Home Vacation Rentals By Owner In Woodstock, VT

Showing 57 Of 57 Vacation Rentals
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Exceptional(1)

$747.72

/ Nightly
Private Vacation Home

Private Retreat in Woodstock, 21 Acres, Views, Dog-friendly

Woodstock, Vermont, United States

Our private, four bedroom house is nestled on 21 acres with incredible views, stone walls and a historic maple sugar shack, and is just minutes from the village green in Woodstock, Vermont. Dog-friendly. Terrific location for a ski getaway, hiking and mountain biking, fall foliage excursions or just a place to disconnect and spend quiet time. The completely furnished yellow house on the hill features a kitchen with an eat-in counter, a sitting area off the kitchen with french doors that open up into the backyard great for grilling and hanging out. The living room has a wood burning stove and opens up to a large farmers porch with Adirondack chairs, great for mountain and wildlife viewing in our meadow. The dining room is bright with amazing views and a large harvest table that seats 8. The family room is perfect for playing games, early morning yoga, and relaxing. Upstairs office. Wireless Internet access throughout. Central heating. Two-car garage with access to snow shoes, sleds and bikes. Wood shed. Fire pit.
Bed 4

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Bath 2

Bath

Sleep 6

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Exceptional(7)

$1130.0

/ Nightly
Private Vacation Home

Premier Woodstock Village Riverfront Home

Woodstock, Vermont, United States

Welcome to one of Woodstock's most iconic houses — Where history, elegance, and nature meet.brbrStep into a piece of cinematic and architectural history in this beautiful home—once the set of the classic film Dr. Cook’s Garden staring Bing Crosby and Blythe Danner (Gwyneth Paltrow's mom). brbrThis elegant, thoughtfully appointed home offers a truly unique Vermont experience. From its timeless design to its peaceful riverfront garden setting, every detail invites you to relax, explore, and immerse yourself in the rich heritage of one of Vermont’s most beloved towns.brbrSpend quality time together enjoying the riverside fire pit, relaxing and dinning on the back porch overlooking the river, or playing corn hole or classic board games, and let the youngest guests explore the tiny fairy houses at the front of the home - magical little touches that spark imagination and smiles.brbrThis home spans over 5,000 square feet, but during your stay, you’ll enjoy exclusive access to a fully self-contained 3-bedroom, 2.5-bath portion of the property. This private space includes its own kitchen, laundry, living areas, and a separate entrance—everything you need for a comfortable and independent stay. The remaining portion of the home is securely closed off and unoccupied while guests are present. No shared spaces, no other occupants—just peace, privacy, and plenty of room to relax. The house is more house than most people need, so we’ve made sure you have exactly what you needbrbrHere, you’ll discover not just comfort, but a place where unforgettable memories are made!brbrWe offer convenient door codes for self-check-in, details will be provided 2 weeks (or less) prior to arrival by email and text message. brbrEarly check-ins or late check-outs: If the property happens to be ready earlier than the standard 3pm check-in time on the day of your arrival, we are happy to offer an early arrival option. brLate check-outs must be confirmed 2 day prior to the date of departure.brbrYour comfort is my priority! I’m always here to help make your stay comfortable and memorable. Guests are welcome to contact me anytime between 8:00 AM and 8:00 PM, 7 days a week—you’ll receive my personal cell number before your arrival for easy communication.brbrI always check in to ensure everything is going smoothly, but I also respect your privacy and space. Whether you’d like local recommendations, assistance during your stay, or simply peace and quiet, I’m happy to follow your lead.brbrPrime Location:brThis home is ideally situated to make the most of everything Woodstock has to offer. A 5-minute walk over the iconic Middle Covered Bridge brings you to the village’s shops, restaurants, and the Woodstock Inn. Outdoor enthusiasts will love the proximity to the Billings Farm and Museum and Marsh-Billings-Rockefeller National Historical Park, both just steps away. Hiking trails up Mount Tom and through the Park begin right across the street.brFor winter sports lovers, the Saskadena Six ski area is just a 7-minute drive, while the Killington Skyeship Base Lodge is a quick 20-minute trip. Okemobrand Pico ski areas are also within easy reach.brbrHouse Rules: br- Sadly, the stone fireplace cannot be usedbr- Reservation holder must be minimum 25 years of agebr- All guests must be counted in the reservation. br- Check-in time is 3:00 p.m. Check-out time is 11:00 a.m.br- This is a No Pets propertybr- This is a No Smoking propertybr- Please contact us for commercial photography and filming usebrbrTown of Woodstock registration #002018
Bed 3

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Bath 2

Bath

Sleep 6

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Exceptional(10)

$487.52

/ Nightly
Private Vacation Home

Genuine Farm! - The Homestead at Winterfound Farm

Woodstock, Vermont, United States

Summary:brbrNestled on the edge of Woodstock, VT, The Homestead at Winterfound Farm stands as a beacon of history and charm, inviting guests to experience the essence of vintage Vermont. This long standing farmhouse, once a thriving moss farm, combines charm with the pastoral beauty of its surroundings.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbr*2027 Winter Seasonal Program - Ask How to Save 35%brbrbrbrThe Space:brbrThe Homestead at Winterfound Farm, Home Features:brbr• 5 Bedroom, 3 Bath - Available for up to 8 Guests!brbr• Well-Appointed Kitchen with All the Essentialsbrbr• Large Hearth Fireplacebrbr• Experience the Rhythms of our Farm - Farm Animals!brbr• Free WiFi & Smart TVsbrbr• Pack 'n play and/or high chair may be available upon request (subject to availability)brbrbrbrStep through the door and find yourself amidst sprawling acres of lush grass and open fields, the perfect prelude to miles of scenic trails winding through the verdant hillsides of Vermont. The property is also home to a natural pond and a working farm, where guests can enjoy the sights and sounds of farm life from a distance to appreciate its charm. This house was built in 1778. At around 250 years old, it is the oldest home in Barnard and a real working farm. While it has the quirks you'd expect from an authentic historic home, its character, warmth, and classic Vermont charm make it a truly special place to stay.brbrbrbrThe main family room balances historical authenticity with modern comfort, featuring plush new furniture arranged to create a warm, inviting space for gatherings. The well-appointed kitchen is equipped with all essentials for preparing delightful meals, ideally enjoyed outdoors while admiring the expansive views of the countryside. Next to the kitchen, a quaint breakfast table for four offers a cozy nook by the woodstove, ideal for enjoying morning coffee and the picturesque outdoor scenery. Just a few steps out the backdoor leads to a large hot tub overlooking the backyard space.brbrbrbrExplore the rich heritage of each room on the first floor. The study houses a complete collection of National Geographic issues, while the den boasts a large hearth fireplace to warm up by after a day of outdoor adventures. The ground floor also hosts a master bedroom with a king-sized bed and abundant natural light, providing a tranquil retreat. Upstairs, the sleeping quarters feature four bedrooms and two bathrooms to accommodate various needs: two rooms with full beds, a bunk room with a full bed under a twin, and another bedroom with a full bed and plenty of storage space.brbrbrbrThe property includes several farm structures that seamlessly integrate into the historic Vermont farmhouse scenery, further enhancing the authentic experience. At The Homestead at Winterfound Farm, every detail is carefully curated to ensure your stay captures the historical and natural beauty of Vermont. Book your visit and step into a picturesque world where history and modern comfort meet amidst the tranquility of Woodstock, VT. Revel in breathtaking views of the valley and our vibrant farm, enhanced by a suite of thoughtfully curated amenities. Experience the rhythms of our farm as you observe a variety of animals in their natural setting. You may even spot our on-site farmer tending to the land! Venture from your doorstep to discover extensive VAST trails that wander past our scenic pond—perfect for hiking, biking, and soaking in Vermont’s natural splendor.brbrbrbrFor relaxation, unwind in our private covered hot tub or enjoy the serene waters of the pond. Winter brings the thrill of skiing, with our property conveniently located just a short drive from the premier ski resorts of Quechee, PICO, and Killington, and only minutes from Saskadena Six. Golf enthusiasts will find a paradise here, with many golf courses within a 50-mile radius, offering a variety of challenging layouts and stunning landscapes that cater to all skill levels. During the summer, bask in the picturesque beauty of our farm and the vibrant, changing foliage in autumn.brbrbrbrOur farmhouse marries rustic charm with modern amenities, providing you a unique opportunity to experience a tranquil countryside retreat unlike any other. This is a place where nature's beauty and homely comforts converge seamlessly, making every day a new opportunity for discovery and relaxation. Don’t miss your chance to enjoy a serene, high-end getaway at The Homestead at Winterfound Fields. Book your stay today and step into a world of adventure, relaxation, and golf in the heart of Vermont.brbrbrbrbrbr*2027 Winter Seasonal Program (Long-Term Reservations): Looking ahead to ski season Make Vermont home for the season with Portoro Homes’ 2027 Winter Seasonal Program. It’s the perfect way to enjoy an extended stay near the mountains, cozy up for the season, and experience winter the right way. Designed for guests seeking a seamless extended stay in professionally managed homes across sought-after winter destinations. Plan ahead and save 35%. Reach out now to learn more about seasonal availability and details.brbrbrbr*Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Field and Farm by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.brbrbrbrThings to See & Do:brbr• Local Fun: horseback riding, hiking, fishing, skiing, golf & more!brbr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbrbr• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National, Killington Mountain Coursebrbr• Explore: Mount Peg trail system, Hike Mount Tom, Historic Covered Bridge Tour, Billings Farm and Museum, Hike the Quechee Gorge “Vermont's Little Grand Canyon”, Visit the charming village of Quechee, take in the views of the Ottauquechee Riverbrbr• Museums: Billings Farm & Museum, Hood Museum of Art, Montshire Museumbrbr• Local Markets: Gillingham's, Woodstock Farmers Market, Feast and Field Market, Mac’s Marketbrbr• Local Restaurants & Shoppingbrbr- Restaurants: The Prince & The Pauper Restaurant, Worthy Kitchen, Mon Vert Café, Simon Pearce Restaurant, Cloudland Farm, Kelly Way Gardens, Village Butcher, Dr. Coburn's Tonicbrbr- Shops: Sudie’s, VT Flannel Co., Woodstock Sports, Yankee Bookstore, Red Wagon Toy Company, Farmhouse Pottery, Simon PearcebrbrbrbrAnnual Festivals & Events:brbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Covered Bridges Half Marathonbrbr• Feast and Fieldbrbr• Taste of Woodstockbrbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• Wassail Weekendbrbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Woodstock Art Festivalbrbr• Hunter Jumper Show brbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrVillage of Woodstock Rental Registration Number #brbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Field and Farm by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
Bed 5

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(7)

$490.15

/ Nightly
Private Vacation Home

200ac, Views! 10min to Town - Scenic Ridge Retreat

Woodstock, Vermont, United States

Summary:brbrEscape to the beauty of Woodstock with a stay at this delightful private cabin. Enjoy endless family fun and relaxation no matter what the season is as you immerse yourself in the stunning surroundings. brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*This is a no pet/animal home.brbr*2027 Winter Seasonal Program - Ask How to Save 35%brbrbrbrThe Space:brbrScenic Ridge Retreat, Home Features:brbr• 4 Bedroom, 3 Bath - Available for up to 8 Guests!brbr• Relax on the Porch with Stunning Viewsbrbr• Cozy Wood-Burning Fireplacebrbr• Woodstock is Just 3 Miles From Your Doorstepbrbr• Free WiFi & Smart TVsbrbr• Pack 'n play and/or high chair may be available upon request (subject to availability)brbrbrbrThis peaceful retreat is at the end of a quiet Vermont road and has been thoughtfully designed to provide you with everything you need for a memorable stay. Perched high up with breathtaking views year-round, this cabin is the perfect spot for outdoor enthusiasts, with direct access to the Appalachian Trail, Saskadena Six, mountain biking, hiking, and ski trails all waiting at your doorstep for you to discover.brbrbrbrThe quintessential historic village of Woodstock is just three miles from your doorstep, offering a wealth of local markets, shops, restaurants, and unique attractions to explore during your stay. But with so much to offer right on your doorstep, you may not even want to leave! Spend your days exploring the natural beauty of your surroundings or simply relax on the porch and soak up the stunning views. Inside the cabin, you'll find everything you need for a comfortable stay. The well-appointed living area boasts plenty of natural light, comfortable seating, and a cozy wood-burning fireplace. The kitchen comes fully equipped with everything needed to prepare meals during your stay, and the dining area provides the perfect spot to enjoy a home-cooked meal with loved ones. The cabin features four bedrooms, each with its own unique charm and style. The primary bedroom boasts a comfortable King-sized bed and stunning views of the surrounding countryside. The other bedrooms offers a Queen downstairs, two twin beds and a comfortable double bed for additional guests.brbrbrbrWith attractions such as Saskadena Six (steps from your front door), Mt. Tom, Billings Farm and National Park, Silver Lake, Barnard, Quechee Gorge and State Park, Dartmouth College in Hanover, NH, Killington Ski Resort, and Okemo Mountain Resort all located within easy reach, you'll have no shortage of things to see and do during your stay.brbrbrbrbrbr*2027 Winter Seasonal Program (Long-Term Reservations): Looking ahead to ski season Make Vermont home for the season with Portoro Homes’ 2027 Winter Seasonal Program. It’s the perfect way to enjoy an extended stay near the mountains, cozy up for the season, and experience winter the right way. Designed for guests seeking a seamless extended stay in professionally managed homes across sought-after winter destinations. Plan ahead and save 35%. Reach out now to learn more about seasonal availability and details.brbrbrbr*Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Field and Farm by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.brbrbrbrThings to See & Do:brbr• Local Fun: horseback riding, hiking, fishing, skiing, golf & more!brbr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbrbr• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National, Killington Mountain Coursebrbr• Explore: Mount Peg trail system, Hike Mount Tom, Historic Covered Bridge Tour, Billings Farm and Museum, Hike the Quechee Gorge “Vermont's Little Grand Canyon”, Visit the charming village of Quechee, take in the views of the Ottauquechee Riverbrbr• Museums: Billings Farm & Museum, Hood Museum of Art, Montshire Museumbrbr• Local Markets: Gillingham's, Woodstock Farmers Market, Feast and Field Market, Mac’s Marketbrbr• Local Restaurants & Shoppingbrbr- Restaurants: The Prince & The Pauper Restaurant, Worthy Kitchen, Mon Vert Café, Simon Pearce Restaurant, Cloudland Farm, Kelly Way Gardens, Village Butcher, Dr. Coburn's Tonicbrbr- Shops: Sudie’s, VT Flannel Co., Woodstock Sports, Yankee Bookstore, Red Wagon Toy Company, Farmhouse Pottery, Simon PearcebrbrbrbrAnnual Festivals & Events:brbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Covered Bridges Half Marathonbrbr• Feast and Fieldbrbr• Taste of Woodstockbrbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• Wassail Weekendbrbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Woodstock Art Festivalbrbr• Hunter Jumper Show brbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrVillage of Woodstock Rental Registration Number #brbrbrbrGetting Around:brbrCome and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you're soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest.brbr brbrTraveling to/around the Upper Valley region of Vermont - Explore by foot, by ski, by bike, or by horseback:brbr• You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car.brbr• Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. brbr brbr brbrAirports:brbr• Burlington (BTV) [VT]brbr• Lebanon (LEB) [NH]brbr• Manchester (MHT) [NH]brbr• Boston Logan (BOS) [MA]brbr brbrPopular Landmarks:brbr• Mount Ascutneybrbr• Norman Williams Public Librarybrbr• Woodstock Town Hallbrbr• Marsh Billings Rockefeller Historical Sitebrbr• The New England Falconrybrbr• President Calvin Coolidge State Historic Sitebrbr• Sugarbush Farmbrbr• Hanover, home to Dartmouth UniversitybrbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Field and Farm by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
Bed 4

Bed

Bath 3

Bath

Sleep 8

Sleeps
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Exceptional(7)

$486.44

/ Nightly
Private Vacation Home

Views! Sauna Historic - Woodstock Riverside Escape

Woodstock, Vermont, United States

Summary:brbrStep into 200 years of history at this 1825 riverside home served as a coach house and tea house in the early 1900s, just a short walk from Woodstock Village. Wake up to the sound of the river from the covered porch, unwind in the private sauna, and relax in the hammock overlooking the water. Three bedrooms, 2.5 baths, and an open kitchen/living area with original wide-plank floors, a working fireplace, and a library filled with books.brbrbrbrThe stone patio and terraced gardens lead right down to the river. Grill out, dine al fresco, or simply sit and watch the water flow by.brbrbrbrHighlights: Private sauna, riverside hammock, stone patio, covered porch with river views, walk to village shops and restaurants, jacuzzi tub, 2,186 sq ft, sleeps 6.brbrbrbrThe Space:brbrWoodstock Riverside Escape, Home Features:brbr• 3 Bedroom, 2.5 Bath - Available for up to 6 Guests!brbr• Only a Short Walk to the Villagebrbr• Fireplace in Living Roombrbr• Sauna in Lower Level, Charcoal Grill in Backbrbr• Free WiFi / Smart TVsbrbr• Pack 'n play and/or high chair may be available upon request (subject to availability)brbrbrbrA thoughtfully decorated three bedroom, two and a half bathroom house that comfortable sleeps six, it’s the perfect mix of modern and classic New England. Only a short walk to the Village, this home is a great launching point to enjoy all that the Green Mountain state offers – whether it’s the hundreds of miles of surrounding recreational trails or Killington Ski Resort (the East Coast’s largest ski area, only 20 minutes away).brbrbrbrThe first floor is furnished comfortably with an open kitchen living and dining room space and 1/2 bath, along with master bedroom, private bath and library. There is a working fireplaces in the library for chilly fall evenings. On the second floor there are two additional bedrooms, an office/sitting area and a bathroom with a jacuzzi bathtub. Exceptional stonework in the back with pathways and a terrace – all exceptionally outline amazing views of a covered bridge, a lovely spot for dining outdoors or just relaxing by the river. You can nap or read in the hammock or on the covered porch off the living room, enjoy the beautiful plantings and gardens that the owners have lovingly created from a private bench.brbrbrbrbrbr*2027 Winter Seasonal Program (Long-Term Reservations): Looking ahead to ski season Make Vermont home for the season with Portoro Homes’ 2027 Winter Seasonal Program. It’s the perfect way to enjoy an extended stay near the mountains, cozy up for the season, and experience winter the right way. Designed for guests seeking a seamless extended stay in professionally managed homes across sought-after winter destinations. Plan ahead and save 35%. Reach out now to learn more about seasonal availability and details.brbrbrbr*Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Field and Farm by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.brbrbrbrThings to See & Do:brbr• Local Fun: horseback riding, hiking, fishing, skiing, golf & more!brbr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbrbr• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National, Killington Mountain Coursebrbr• Explore: Mount Peg trail system, Hike Mount Tom, Historic Covered Bridge Tour, Billings Farm and Museum, Hike the Quechee Gorge Vermont's Little Grand Canyon, Visit the charming village of Quechee, take in the views of the Ottauquechee Riverbrbr• Museums: Billings Farm & Museum, Hood Museum of Art, Montshire Museumbrbr• Local Markets: Gillingham's, Woodstock Farmers Market, Feast and Field Market, Mac's Marketbrbr• Local Restaurants & Shoppingbrbr- Restaurants: The Prince & The Pauper Restaurant, Worthy Kitchen, Mon Vert Café, Simon Pearce Restaurant, Cloudland Farm, Kelly Way Gardens, Village Butcher, Dr. Coburn's Tonicbrbr- Shops: Sudie's, VT Flannel Co., Woodstock Sports, Yankee Bookstore, Red Wagon Toy Company, Farmhouse Pottery, Simon PearcebrbrbrbrAnnual Festivals & Events:brbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Covered Bridges Half Marathonbrbr• Feast and Fieldbrbr• Taste of Woodstockbrbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• Wassail Weekendbrbr• Woodstock Art Festivalbrbr• Hunter Jumper ShowbrbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrVillage of Woodstock Rental Registration Number #brbrbrbrGetting Around:brbrCome and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you're soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest.brbr brbrTraveling to/around the Upper Valley region of Vermont - Explore by foot, by ski, by bike, or by horseback:brbr• You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car.brbr• Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. brbr brbr brbrAirports:brbr• Burlington (BTV) [VT]brbr• Lebanon (LEB) [NH]brbr• Manchester (MHT) [NH]brbr• Boston Logan (BOS) [MA]brbr brbrPopular Landmarks:brbr• Mount Ascutneybrbr• Norman Williams Public Librarybrbr• Woodstock Town Hallbrbr• Marsh Billings Rockefeller Historical Sitebrbr• The New England Falconrybrbr• President Calvin Coolidge State Historic Sitebrbr• Sugarbush Farmbrbr• Hanover, home to Dartmouth UniversitybrbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Field and Farm by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
Bed 3

Bed

Bath 2

Bath

Sleep 6

Sleeps
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$320.12

/ Nightly
Private Vacation Home

Fireplace, Library - 21 Mountain Ave, Woodstock*

Woodstock, Vermont, United States

Summary:brbrEscape to this enchanting retreat and experience the perfect blend of luxury, comfort, and convenience in the heart of Historic Woodstock, VT.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbr21 Mountain Ave, Home Features:brbr• 4 Bedroom, 3.5 Bath - Available for up to 8 Guests!brbr• Cozy Fireplace & Librarybrbr• Spacious Gourmet Kitchen, Updated Appliancesbrbr• Dedicated Office Space -- Work Remotely!brbr• Free WiFi & Smart TVsbrbr• Pack 'n play and/or high chair may be available upon request (subject to availability)brbrbrbrWelcome to your dream getaway nestled in the heart of historic Woodstock, VT. This charming home awaits you on a peaceful street, offering the perfect starting point for your adventure. As you enter through the side entrance, you'll be greeted by a spacious and inviting gourmet kitchen, complete with updated appliances that are ideal for entertaining guests. Just beyond the kitchen lies the cozy lounge area, featuring a large sectional couch and a dedicated office space for those who need to catch up on work or simply unwind.brbrbrbrAdjacent to the lounge area, you'll discover the elegant formal dining room, boasting a grand dining table that comfortably seats 8 guests and a working fireplace, setting the scene for memorable dining experiences. Venture further through the foyer to find the inviting living room and library area, where you can enjoy relaxing evenings with your fellow guests, whether it's a spirited game night or a cozy movie marathon after a day of exploring historic Woodstock. As you ascend to the second floor, you'll find the tranquil sleeping quarters and the luxurious primary suite. Tucked away at the back of the home, the private primary suite offers an ensuite bathroom complete with a spacious jacuzzi tub and his and her sinks, providing the ultimate retreat.brbrbrbrContinuing down the hall, you'll discover the next bedroom featuring a queen bed and a full bathroom conveniently located just next door, ensuring a restful night's sleep in the utmost comfort. At the front of the home, two beautifully appointed bedrooms await, each offering a queen bed and unique amenities. To the right of the stairs, you'll find a generously sized bedroom with a queen bed and a cozy sitting area, perfect for unwinding with a good book. Meanwhile, the other bedroom boasts a queen bed and a dedicated office space, providing the ideal balance of comfort and productivity.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Field and Farm by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.brbrbrbrThings to See & Do:brbr• Local Fun: horseback riding, hiking, fishing, skiing, golf & more!brbr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbrbr• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National, Killington Mountain Coursebrbr• Explore: Mount Peg trail system, Hike Mount Tom, Historic Covered Bridge Tour, Billings Farm and Museum, Hike the Quechee Gorge “Vermont's Little Grand Canyon”, Visit the charming village of Quechee, take in the views of the Ottauquechee Riverbrbr• Museums: Billings Farm & Museum, Hood Museum of Art, Montshire Museumbrbr• Local Markets: Gillingham's, Woodstock Farmers Market, Feast and Field Market, Mac’s Marketbrbr• Local Restaurants & Shoppingbrbr- Restaurants: The Prince & The Pauper Restaurant, Worthy Kitchen, Mon Vert Café, Simon Pearce Restaurant, Cloudland Farm, Kelly Way Gardens, Village Butcher, Dr. Coburn's Tonicbrbr- Shops: Sudie’s, VT Flannel Co., Woodstock Sports, Yankee Bookstore, Red Wagon Toy Company, Farmhouse Pottery, Simon PearcebrbrbrbrAnnual Festivals & Events:brbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Covered Bridges Half Marathonbrbr• Feast and Fieldbrbr• Taste of Woodstockbrbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• Wassail Weekendbrbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Woodstock Art Festivalbrbr• Hunter Jumper Show brbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrVillage of Woodstock Rental Registration Number #brbrbrbrGetting Around:brbrCome and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you're soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest.brbr brbrTraveling to/around the Upper Valley region of Vermont - Explore by foot, by ski, by bike, or by horseback:brbr• You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car.brbr• Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. brbr brbr brbrAirports:brbr• Burlington (BTV) [VT]brbr• Lebanon (LEB) [NH]brbr• Manchester (MHT) [NH]brbr• Boston Logan (BOS) [MA]brbr brbrPopular Landmarks:brbr• Mount Ascutneybrbr• Norman Williams Public Librarybrbr• Woodstock Town Hallbrbr• Marsh Billings Rockefeller Historical Sitebrbr• The New England Falconrybrbr• President Calvin Coolidge State Historic Sitebrbr• Sugarbush Farmbrbr• Hanover, home to Dartmouth UniversitybrbrbrbrOther Things to Note:brbrPlease pay close attention to following the house rules. Non compliance could result in sizable fines.brbr- All guests staying at an Field and Farms Vacation Homes by Portoro (Portoro Homes) are required to sign (esignature) a rental agreement and complete identity registration.brbr- Age restrictions apply. Reservation holder must be 25 years of age.brbr- Upon arrival, we aim to ensure your safety, proper access to the home, and guest features. Should you have any questions, please don't hesitate to reach out to Field and Farm by Portoro directly. brbr- Known damages incurred during your stay must be reported to the property manager immediately. brbr- Before check in, we will send you detailed directions to ensure a seamless arrival.brbr- Check-in time is 3:00 p.m. Check-out time is 10:00 a.m.brbr- We cannot guarantee early check ins or late checkouts. When it is possible to check in early or check out late, there will be a fee for anything outside of a one hour window within our standard times. If your need for an early check in or late check out is great, your best option is to book an additional night.brbr- Some homes have cameras for external monitoring only.brbr- In the State of Vermont and in Windsor County, all hotel and vacation rental hosts are required to collect hotel tax. We collect these taxes within the booking transaction. brbr- There is no guard around the pools. - Use at your own risk.brbr- This is a No Smoking property. Penalty fees for violations will apply and you may be asked to vacate the premises with no refund at the discretion of the Host.brbrbrbr- Animals/Pets -- Dogs Only, Guidelines and Fee*brbrAnimals/pets must be disclosed prior to reservation arrival date. Only dogs are permitted in “Pet-Friendly” Property listings. Allowed number of dogs will be expressly stated in the listing and a $150.00 fee per animal/pet is required. Animals/pets are not permitted anywhere on the premises unless prior approval is obtained. Any unauthorized animals/pets at the property will result in a $150.00 per day / per animal/pet fee, and may result in your reservation being canceled, and you may be required to vacate from the Property. brbr-- 21 Mountain Ave, Woodstock allows for a maximum of 1 dog at $150.00 per dog per stay.
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$574.76

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Private Vacation Home

Real Farm! - The Barn at Winterfound Farm

Woodstock, Vermont, United States

Summary:brbrWelcome to our beautifully renovated Barn located just ten minutes away from the historic town of Woodstock. Enjoy breathtaking views of the valley and the surrounding farm, while indulging in the various amenities we have to offer.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*This is a no pet/animal home.brbr*2027 Winter Seasonal Program - Ask How to Save 35%brbrbrbrPlease note that this is a working farm. The driveway is shared with the Farm Manager, who happily will show you around! Their living quarters are in a separate barn on the property, across from where you'll stay.brbrbrbrThe Space:brbrThe Barn at Winterfound Farm, Home Features:brbr• 3 Bedroom, 2 Bath - Available for up to 8 Guests!brbr• All Bedrooms Feature Large Windows & Viewsbrbr• Chef's Dream! Well-Equipped Kitchenbrbr• Private Covered Hot Tub brbr• Free WiFi & Smart TVsbrbr• Pack 'n play and/or high chair may be available upon request (subject to availability)brbrbrbrExperience the rhythms of our farm as you observe a variety of animals in their natural setting. You may even spot our on-site farmer tending to the farm! With 3 bedrooms and 2 bathrooms, our farmhouse is perfect for families or groups of friends seeking a serene escape. Take advantage of the miles and miles of VAST trails right outside your doors and past the idyllic pond, perfect for hiking, biking, and exploring the beauty of Vermont. Unwind in our private covered hot tub, perfectly placed to offer stunning views of the farm and valley. Located just a short drive from Quechee, PICO, and Killington Ski Resorts, our property is the perfect base for a winter skiing adventure. We are just minutes away from Saskadena Six. In the summer, enjoy the picturesque beauty of the surrounding farm and the vibrant foliage of autumn. With every modern amenity you could need at hand, our farmhouse offers you a unique opportunity to experience a peaceful countryside getaway like no other. Don't miss out on the chance to stay in our rustic yet high-end getaway. brbrbrbrThe moment you step through the double front doors of this stunning open-concept home, you are immediately enveloped by the charming ambiance that only a cozy farmhouse can provide. Boasting two bedrooms on the first level, this home is perfect for families or groups of friends looking to experience the tranquility of Vermont country living. One of the bedrooms features a bunk bed, with a full-size bed on the bottom and a twin-size bed on top. A trundle bed is also available, offering ample sleeping space for up to four guests. The full bathroom on this level includes a shower, while the stackable washer and dryer found between the bathroom and the bunk room make for convenient and practical living. Across the hall from the bathroom, you will find the Queen room - a peaceful and serene retreat for two. All bedrooms feature large windows, revealing spectacular views of the surrounding countryside, allowing guests to immerse themselves in the natural beauty of this idyllic location.brbrbrbrAt the back of the house lies an inviting sitting room, complete with cozy furnishings and access to a large stone patio overlooking the verdant garden and valley beyond. This is the perfect space to unwind, relax, and take in the breathtaking views of the surrounding landscape. Head upstairs for even more entertainment and relaxation, with a plush King-size bed awaiting you in the primary bedroom. The open-concept space on this level includes a charming living room to your right, with a central woodstove surrounded by plush furnishings. Separating the living space from the gourmet kitchen is the spacious dining area, where a stunning natural wood table seats up to eight guests. The views of the valley from the dining area are spectacular.brbrbrbrThe kitchen is a chef's dream, equipped with every appliance and spice needed to create culinary masterpieces for friends and family. Between the primary bedroom and the kitchen, guests will also find the second full bathroom with a deep soaking tub and shower, offering the ultimate in relaxation and pampering. Guests are invited to enjoy the charm of the farm by observing the animals from a distance as they go about their day. And for those looking to soak up the natural beauty of the area, there is a covered hot tub equipped to accommodate up to four people, perfect for enjoying stunning views of the valley while soaking away any and all cares.brbrbrbrBed setup: 1st Floor: Bunk bed with twin over double and trundle bed (sleeps 4), Queen bed (sleeps 2) / 2nd Floor: King bed (sleeps 2)brbrbrbrbrbr*2027 Winter Seasonal Program (Long-Term Reservations): Looking ahead to ski season Make Vermont home for the season with Portoro Homes’ 2027 Winter Seasonal Program. It’s the perfect way to enjoy an extended stay near the mountains, cozy up for the season, and experience winter the right way. Designed for guests seeking a seamless extended stay in professionally managed homes across sought-after winter destinations. Plan ahead and save 35%. Reach out now to learn more about seasonal availability and details.brbrbrbr*Long Term Reservations: Guests booking reservations lasting 55 nights or more are responsible for and agree to pay all utilities which may include, but are not limited to: Propane, Oil, Electricity, Firewood, Trash Removal, and Snow Removal. These charges will be assessed within 60 days after check-out. Reservations with any dates between 1/4/27 and 3/6/27 must be 55 nights or more.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Field and Farm by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.brbrbrbrThings to See & Do:brbr• Local Fun: horseback riding, hiking, fishing, skiing, golf & more!brbr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbrbr• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National, Killington Mountain Coursebrbr• Explore: Mount Peg trail system, Hike Mount Tom, Historic Covered Bridge Tour, Billings Farm and Museum, Hike the Quechee Gorge “Vermont's Little Grand Canyon”, Visit the charming village of Quechee, take in the views of the Ottauquechee Riverbrbr• Museums: Billings Farm & Museum, Hood Museum of Art, Montshire Museumbrbr• Local Markets: Gillingham's, Woodstock Farmers Market, Feast and Field Market, Mac’s Marketbrbr• Local Restaurants & Shoppingbrbr- Restaurants: The Prince & The Pauper Restaurant, Worthy Kitchen, Mon Vert Café, Simon Pearce Restaurant, Cloudland Farm, Kelly Way Gardens, Village Butcher, Dr. Coburn's Tonicbrbr- Shops: Sudie’s, VT Flannel Co., Woodstock Sports, Yankee Bookstore, Red Wagon Toy Company, Farmhouse Pottery, Simon PearcebrbrbrbrAnnual Festivals & Events:brbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Covered Bridges Half Marathonbrbr• Feast and Fieldbrbr• Taste of Woodstockbrbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• Wassail Weekendbrbr• Woodstock Apples and Crafts Fair and food truck festivalbrbr• Woodstock Art Festivalbrbr• Hunter Jumper Show brbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrVillage of Woodstock Rental Registration Number #brbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Field and Farm by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
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Exceptional(48)

$1041.22

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Private Vacation Home

Woodstock Village Green Location, Walk Everywhere, River Patio, Covered Bridge

Woodstock, Vermont, United States

Park your car and put away your keys for your stay. 1823 Village Green Colonial. 4 bedrooms, 2 baths (both on the second floor). Sleeps 8. br brRiver location with sweeping views of the Woodstock Middle Covered Bridge and Mount Tom from all back rooms. Fully equipped kitchen, and gracious dining room to host your Thanksgiving, Christmas or holiday dinner. brbrDirectly across from Woodstock Inn. Perfect for people who need kitchen and living areas. Close to Killington, Pico, Suicide Six Ski areas. Walk to trails on MT Tom and Mt Peg.brbrNo Parties or Hosted or Catered Events are allowed. No unsupervised children on the terrace. brbrBack terrace and stairs down are uneven stone and pebbles. Not suitable for young children, elderly or others with unsure footing. Back terrace is not maintained during winter/snow months and not accessible.brbrOnly guests noted in your reservation request are allowed.
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$276.85

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Apartment

Delightful Cozy Space in Woodstock Village

Woodstock, Vermont, United States

Walking distance to everywhere in the Village and Mt Tom and Mt Peg. Parking for 2 cars, beautiful outdoor deck overlooking woods, quiet. Apt is private and above garage. Outdoors clean and tastefully maintained. Beautiful new hardwood floors, two sunny skylights in kitchen and bedroom. Mix of new and antique furniture around the unit. Plenty of closet space at entry and in bedroom. Two HD TVs in unit, one in Living Room and one in Bedroom. Wireless internet included.
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$403.47

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Private Vacation Home

Walk to Trails & Village +Pets - Highland Cabin

Woodstock, Vermont, United States

Summary:brbrEscape to Highland Cabin, a sunlit Woodstock retreat—close to town yet perched on a steep, quiet hillside for extra privacy. Start your morning with a peaceful walk to the Mt. Tom trailhead or enjoy a leisurely 15-minute stroll down into the village and the Woodstock Inn. After exploring, come home to vaulted ceilings, forest views, and a freshly updated, pet-friendly haven that sleeps up to 4 in the heart of Vermont.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*Pet Friendly, fee applies per pet.brbrbrbrThe Space:brbrHighland Cabin Home Features:brbr• 1 Bedroom, 1 Bath - Available for up to 4 Guests!brbr• Stainless Steel Appliances in Updated Kitchenbrbr• Remote Work Desk: Monitor & Keyboardbrbr• Solar Powered!brbr• Free WiFi & Smart TVbrbr• Pack 'n play and/or high chair may be available upon request (subject to availability)brbrbrbrHighland Cabin is your cozy, sunlit retreat nestled at the foothills of Mount Peg in charming Woodstock, Vermont—just minutes from the village and perfectly positioned for both relaxation and adventure. Perched on a steep hillside, the cabin offers a peaceful sense of seclusion while still keeping you close to Woodstock’s shops, cafés, and galleries. The Mt. Tom trailhead is also nearby, making outdoor exploration easily accessible. Traveling with a pet Furry companions are welcome at Highland Cabin! The large open yard and neighborhood trails are perfect for pets to stretch their legs and explore. Please note: there is a pet fee required for each stay—just let us know if you’ll be bringing your four-legged friend.brbrbrbrPerfect for couples, small families, or solo travelers seeking romance, relaxation, or a quiet work retreat, this freshly updated pet-friendly one-bedroom cottage blends classic New England character with stylish modern touches. Step inside to warm wood floors and an open living and dining space, with natural light pouring in through oversized windows that frame beautiful forest views. The spacious king bedroom features vaulted ceilings and an Avocado bed, offering a serene place to recharge after a day’s adventure. A sleeper sofa in the living area (with bedding in the corner cabinet) comfortably accommodates two additional guests, bringing total occupancy to four. You’ll also find a spa-like full bathroom with a soaking tub/shower combo and the convenience of an in-unit washer and dryer for longer stays.brbrbrbrThe welcoming living area offers a comfy sofa, games tucked away in the corner cabinet, and a smart TV on a full-motion mount—perfect for movie nights, game nights, or relaxed downtime. The full kitchen features stainless steel appliances and a beautiful butcher block countertop, ideal for preparing cozy meals at home.brbrbrbrWorking remotely A thoughtfully designed workspace awaits, complete with a desk, ergonomic chair, monitor, and keyboard. Positioned across from the cheerful breakfast bar and kitchen, it offers calming forest views while you work or create. Enjoy year-round comfort with reliable heating, fast WiFi, solar power, and hassle-free parking right at the cabin.brbrbrbrBegin and end your days in the large enclosed porch, offering a convenient bench and shoe rack for easy gear changes. Two classic red rocking chairs are yours to use—bring them out to the front yard to enjoy fresh Vermont air and peaceful mountain views with your morning coffee or evening glass of wine. In winter, the porch serves as a practical mudroom; in the warmer months, it becomes a tranquil sitting area filled with natural light.brbrbrbrWhether you’re skiing at nearby resorts, exploring scenic woodland trails, or simply unwinding in your hillside retreat, Highland Cabin is the perfect base for your Vermont getaway. Experience the beauty, charm, and relaxation that Woodstock has to offer—for you and your furry family members! Let Highland Cabin be your home for your next Vermont escape.brbrbrbrPlease Note: The property is located on an uphill road. During the winter months, we strongly recommend guests use a four-wheel-drive (4WD) vehicle to ensure safe and reliable access to the property.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Field & Farm Vacation Homes by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrThe Neighborhood:brbrWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.brbr brbrThings to See & Do:brbr• Explore: Take the Historic Covered Bridge Tour, Hike the Quechee Gorge,Whistlepig Tasting Room, Visit the Dream Alpaca Farmbrbr• Covered Bridge Tours: Quechee Covered Bridge, Taftsville Covered Bridge, Packered Hill Covered Bridge, Martins Mill Covered Bridge, Willard Twin Covered Bridges, Martins Mill Covered Bridge, Middle Covered Bridge, Waitsfield Village Covered Bridgebrbr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbrbr• Award-Winning Golf Courses: Lakeland Golf Course, Highland Golf Course, Quechee Lakes Country Club, Woodstock Country Club, Green Mountain National, Killington Mountain Coursebrbr• Museums: Simon Pearce Mill, B.f. Southgate Antiques Collaborative, Glenn Suokko Gallery, The Ice House Museum, Vermont Institute of Natural Science, Billings Farm and Museum, Montshire Museum of Science, Hall Art Foundation, Old Windsor Constitution House, Woodstock History Centerbrbr• Local Markets: Jake’s Quechee Market, Quechee General Store - Cabot Stationbrbr• Local Restaurants & Shoppingbrbr- Restaurants: The Skinny Pancake, Public House Pub Quechee, Simon Pearce, Chef Brad’s CrazySide, Thyme Restaurant Vermont, Dewey’s at Quechee Club, Quechee Club, Soulfully Good Cafe, Au Comptoirbrbr- Shops: Quechee Gorge Village, The Vermont Spot, Quechee General Store - Cabot Station, Vermont Antique Mall, Fat Hat Clothing Company, Vermont Alpaca Store, Simon Pearcebrbr brbrAnnual Festivals & Events:brbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• White Mountain Boogie and Blues Festivalbrbr• Vermont State FairbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbr brbrVillage of Quechee Rental Registration Number #brbrbrbrGetting Around:brbrCome and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you're soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest.brbr brbrTraveling to/around the Upper Valley region of Vermont:brbr• You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car. Please keep in mind all wheel drive is recommended for the winter months as it is a steep drive to the home as well as other local areas.brbr• Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. brbr• You can also explore by foot, by ski, or by horseback!brbr brbrAirports:brbr• Burlington (BTV) [VT]brbr• Lebanon (LEB) [NH]brbr• Manchester (MHT) [NH]brbr• Boston Logan (BOS) [MA]brbr brbrPopular Landmarks:brbr• Mount Ascutneybrbr• Norman Williams Public Librarybrbr• Woodstock Town Hallbrbr• Marsh Billings Rockefeller National Historical Parkbrbr• Saint Gaudens National Historic Sitebrbr• President Calvin Coolidge State Historic Sitebrbr• Alden Partridge Plaquebrbr• Joseph Smith Memorialbrbr• Whale’s Dancebrbr• Largest Zipper in North Americabrbr• Vermont Vietnam Veteran’s Memorialbrbr• Hanover, Home to Dartmouth University
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Exceptional(4)

$2034.67

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Country House

S P R U C E ~ T O P

Woodstock, Vermont, United States

Spruce Top beckons you to explore your surroundings. Kick back and relax in this newly renovatedbr4 bedroom, 4.5 bath property. Just minutes to the Village of Woodstock. The home rests on bluff off of a truly special road of legacy farms and families.brbrLocal favorites like The Farmers Market & Long Trail Brewery are at the end of the road. Less than 10 minutes to Woodstock Village, Bridgewater Village & Saskadena Six Ski Mountain. 20 minutes to Killington Mountain.brThe spacebrYou will enter the home through a gorgeous custom-designed front door, or through the heated, one car garage that both lead into a large mudroom with ample storage...no matter the season there is plenty of space for everything.brbrAs you continue through to the first floor you’ll find a dining space that’s flexible for any party. While a round Restoration Hardware table is in place, an additional 8-person farmhouse style table is available upon request to provide seating for up to 14. The massive kitchen island looks out over the expansive views and spring fed pond. This kitchen calls for loved ones to gather; and serves as one of the several entertaining spaces throughout the home.brbrIn the kitchen, additional details include:br- Breville espresso machinebr- Le Creuset cookwarebr- Simon Pearce & Farmhouse Pottery itemsbr- a stunning La Cornue range imported from France, an oversized Sub-Zero french-door refrigerator, and a Thermador speed oven that makes cooking everything a breeze! Whether you cook routinely, or use vacation as your time to shine...this kitchen will make any chef happy! It has also hosted a professional chef several times for those extra special memories.brbrHeading back towards the main living wing, you’ll pass through the speak-easy inspired bar with original brick flooring & wall, custom cabinetry & a vintage Long Trail Brewery mirror.brbrThere are two adjoining living spaces; well thought-out to allow the adults and kid crew separate areas to hang! The Fireplace Room maintains the original character of the home. It is warm & cozy with a large fireplace, original wide plank floors, a big comfy leather couch, and velvet chairs that evoke conversation over a locally crafted beer or cocktail mixed up in the adjoining bar (fully stocked with bar supplies.) This space is also meant for quiet serenity, perhaps with a book, hot tea, and the crackling fire.brbrThe second living space, The Great Room, is perfect for football, movies, or kids! It features high ceilings, hand-hewn beams, an 80-inch Smart TV, a large sectional sofa, a separate seating area to enjoy the views, and a closet stocked with games, puzzles, and other fun finds like a doll house. This room has a full size bathroom.brbrUpstairs you will find a King guest suite with ensuite bathroom, two additional guest rooms (one queen and one full bed), a laundry room with folding counter and stainless-steel utility sink, and a double vanity bathroom. Finally, enter the primary bedroom through your own office/yoga/relaxation area (equipped with a Peloton – just bring your own shoes!) There are free weights and a foam roller (great after a day of skiing.) As you continue to the bedroom, you will enjoy the most stunning sunrises which can be enjoyed right from a lounge chair or the king-sized Restoration Hardware bed. Included in the Primary suite is a TV, a walk-in closet, and an ensuite bathroom with radiant heat flooring, a charming reclaimed soaking tub and oversized glass-enclosed shower. The views from this shower will allow you to pause and appreciate your escape from reality every time!brbrOUTSIDE you will find exceptional views. In addition:br~ A fan favorite is The Overlook, an outdoor living space with so much charm & character, you may not even go inside! This truly special space is original to the home; cathedral beamed ceilings will keep you undercover, allowing you to continue comfortably enjoying the outdoors even if it's raining. West Elm lounge furniture, a fireplace, Rinnai heater and expansive views lend way to the perfect place to enjoy your morning coffee, or charcuterie & wine. This area is at the very top of the list of what makes this home truly special. It is a Vermont experience you do not want to miss.brbrAdditional Outdoor Features:br~ The RASPBERRY bush: Help yourself to fresh raspberries during the summer season.br~ A large spring-fed pond, with the occasional ducks who pay a visit.br~ A dining area under a vined trellis and surrounding beautiful gardens will transport you to Europe.br~ Adirondack chairs & a Solo Stove: enjoy the views, good conversation & smores. The solo stove has a surround which provides additional safety for the kids.br~ The Gardens: beautiful perennials are showcased throughout the year. Guests love walking the property to explore the beauty that surrounds them.br~ Sledding Hill: fun to be had with provided LL Bean tubes & sledsbrbrbrS P R U C E ^ T O P is a property that was designed to truly unwind and be present in the little moments, nature, as well as bringing together loved ones. We can't wait to host you!
Bed 4

Bed

Bath 4

Bath

Sleep 8

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Exceptional(15)

$580.99

/ Nightly
Private Vacation Home

Wood-Burning Stove, Great for Families - Z1040*

Woodstock, Vermont, United States

Summary:brbrExquisite four bedroom, four bath single family home located within one mile to the Quechee Club and amenities.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*This is a no pet/animal home.brbr*Quechee Club access included; activity fees paid directly to the club.brbrbrbrThe Space:brbrZ1040, Home Features:brbr• 4 Bedroom, 4 Bath - Available for up to 8 Guests!brbr• Open Concept Floorplanbrbr• Upstairs Loftbrbr• Wood Burning Stovebrbr• Free WiFi & Smart TVsbrbr• Pack 'n play and/or high chair may be available upon request (subject to availability)brbrbrbrExcellent home for entertaining family and friends with the open concept floor plan. The main floor has 3 bedrooms and three full bathrooms. Open concept floor plan on the main level with the kitchen opens up to a large living/dining room area. The Master Bedroom suite has it's own private bathroom. Two more bedrooms complete the main level of the home. Upstairs is a fourth bedroom with it's own private bathroom.brbrbrbrBed Setup: King in master, Queen in second, two twins in third, and a Queen in upstairs loft.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Quechee Lakes Rentals by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrbrbrAccess To: The Quechee ClubbrbrThis home offers exclusive access to The Quechee Club. There is something for everyone at The Quechee Club, an outdoor enthusiast's haven and every outdoor whim. brbrbrbrIn the summer months, members and renters can enjoy several outdoor activities. The Club offers two championship 18-hole golf courses, Lakeland & Highland, with stunning scenery and conditions. Tennis courts are spread throughout the community with professional tennis lessons and enjoyable competition. Renters can also enjoy the state-of-the-art aquatic center featuring an indoor & outdoor pool with an active kid's zone. Likewise, you can venture over to the beach at Lake Pinneo and rent a kayak or canoe. Then head to The Club to enjoy a cocktail by the pool, a meal on Dewey's Deck, or fine dining at Davidson's.brbrbrbrIn the winter months, Ski Quechee is our featured amenity. Open Friday through Sunday, take the family out for an exciting day on expertly groomed terrain. You can enjoy our wonderful base lodge and après ski gatherings with activities for the whole family. The Club also maintains heated platform tennis with warming huts through the cold months to keep your paddle game sharp. The Club features a full winter recreational calendar, including snowshoeing, x-country skiing, sledding, and much more! Outside of our seasonal offerings, there is so much more at Quechee. The Club offers a modern fitness center with daily fitness classes and top-notch equipment. Hiking trails are spread throughout the community woods. Quechee is home to several special events and incredible dining experiences. brbrbrbrTo elevate your experience further, indulge in the diverse dining options available at The Club House. brbrFor inquiries regarding fees, amenities and availability, please reach out to Member Services directly at The Quechee Club.brbrbrbrThe Neighborhood:brbrWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.brbr brbrThings to See & Do:brbr• Explore: Take the Historic Covered Bridge Tour, Hike the Quechee Gorge,Whistlepig Tasting Room, Visit the Dream Alpaca Farmbrbr• Covered Bridge Tours: Quechee Covered Bridge, Taftsville Covered Bridge, Packered Hill Covered Bridge, Martins Mill Covered Bridge, Willard Twin Covered Bridges, Martins Mill Covered Bridge, Middle Covered Bridge, Waitsfield Village Covered Bridgebrbr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbrbr• Award-Winning Golf Courses: Lakeland Golf Course, Highland Golf Course, Quechee Lakes Country Club, Woodstock Country Club, Green Mountain National, Killington Mountain Coursebrbr• Museums: Simon Pearce Mill, B.f. Southgate Antiques Collaborative, Glenn Suokko Gallery, The Ice House Museum, Vermont Institute of Natural Science, Billings Farm and Museum, Montshire Museum of Science, Hall Art Foundation, Old Windsor Constitution House, Woodstock History Centerbrbr• Local Markets: Jake’s Quechee Market, Quechee General Store - Cabot Stationbrbr• Local Restaurants & Shoppingbrbr- Restaurants: The Skinny Pancake, Public House Pub Quechee, Simon Pearce, Chef Brad’s CrazySide, Thyme Restaurant Vermont, Dewey’s at Quechee Club, Quechee Club, Soulfully Good Cafe, Au Comptoirbrbr- Shops: Quechee Gorge Village, The Vermont Spot, Quechee General Store - Cabot Station, Vermont Antique Mall, Fat Hat Clothing Company, Vermont Alpaca Store, Simon Pearcebrbr brbrAnnual Festivals & Events:brbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• White Mountain Boogie and Blues Festivalbrbr• Vermont State FairbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbr brbrVillage of Quechee Rental Registration Number #brbrbrbrGetting Around:brbrCome and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you're soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest.brbrbrbrTraveling to/around the Upper Valley region of Vermont - Explore by foot, by ski, by bike, or by horseback:brbr• You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car.brbr• Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas.brbrbrbrAirports:brbr• Burlington (BTV) [VT]brbr• Lebanon (LEB) [NH]brbr• Manchester (MHT) [NH]brbr• Boston Logan (BOS) [MA]brbrbrbrPopular Landmarks:brbr• Mount Ascutneybrbr• Norman Williams Public Librarybrbr• Woodstock Town Hallbrbr• Marsh Billings Rockefeller National Historical Parkbrbr• Saint Gaudens National Historic Sitebrbr• President Calvin Coolidge State Historic Sitebrbr• Alden Partridge Plaquebrbr• Joseph Smith Memorialbrbr• Whale’s Dancebrbr• Largest Zipper in North Americabrbr• Vermont Vietnam Veteran’s Memorialbrbr• Hanover, Home to Dartmouth UniversitybrbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Quechee Lakes Rentals by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.
Bed 4

Bed

Bath 4

Bath

Sleep 8

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$540.27

/ Nightly
Private Vacation Home

Walk to Mt. Peg Trail + Village, Enjoy Porch Views

Woodstock, Vermont, United States

Summary:brbrWoodstock Trail Cottage puts you steps from the Mt. Peg trailhead and an easy walk from the shops, dining, and charm of Woodstock Village. Come home to a cozy, light-filled cape with hardwood floors, an easy open layout, and a covered back porch with seating overlooking the perennial gardens—perfect for coffee, conversation, and four-season Vermont views.brbrbrbrPlease SEE: Other Things to NotebrbrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbrbr*This is a no pet/animal home.brbrbrbrThe Space:brbrWoodstock Trail Cottage, Home Features:brbr• 3 Bedroom, 2 Bath - Available for up to 6 Guests!brbr• Steps To Mt. Peg Trailheadbrbr• Walk To Woodstock Village & The Greenbrbr• Covered Back Porch With Seatingbrbr• Open Kitchen With Dining Area + First Floor Laundrybrbr• Free WiFi & Smart TVbrbrbrbrSleeping Arrangements: brbr- Multi-Level Homebrbr• Bedroom 1 - Queen Bed (1st Floor)brbr• Bedroom 2 - Queen Bed (2nd Floor)brbr• Bedroom 3 - 2 twins (2nd Floor)brbrbrbrWelcome to Woodstock Trail Cottage!brbrbrbrTucked on a quiet dead-end street in the heart of Woodstock Village, this charming circa-1880 Cape pairs walk-to-town convenience with a private covered back porch that quickly becomes everyone’s favorite spot. Set directly across from the Mt. Peg trailhead, it’s easy to start the morning with a hike, then stroll into town for coffee, shopping, and the year-round events on the Historic Woodstock Green. Championship golf, fly fishing, and skiing are all close by, making this a true four-season home base.brbrInside, the cottage blends antique character with an easy, comfortable layout. Hardwood floors run throughout, and the open kitchen anchors the main level with a bright, welcoming flow into the dining area and adjacent sitting space—ideal for lingering breakfasts, shared meals, and relaxed evenings in. A first-floor bedroom pairs with a nearby bath featuring soothing green accents, and the convenience of first-floor laundry makes longer stays feel effortless.brbrbrbrUpstairs, the home continues with two additional bedrooms filled with natural light, along with a sweet library nook that’s perfect for curling up with a book on a rainy day. A second bathroom on this level helps the home live comfortably for groups, with space that suits couples traveling together, families, or friends looking for a classic Woodstock getaway.brbrbrbrOut back, the covered porch is the kind of space you’ll use from the moment you arrive. From the seating area, you look out over the private yard and perennial gardens, with trees framing the view and a calm, tucked-away feel that’s hard to find this close to the village. It’s perfect for morning coffee while the light comes up, après-ski conversations as the day winds down, or a quiet hour with a book while you watch the seasons change. The porch is set up for real lounging and easy gathering, with comfortable seating that turns it into an “extra room” in warm months and a front-row seat to snowfall in winter.brbrbrbrWoodstock Trail Cottage delivers a rare combination of village convenience, trail access, and timeless Vermont charm.brbrbrbrGuest Access:brbrWe offer convenient door codes for self-check-in. Field & Farm Vacation Homes by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbrbrbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrbrbrNOTE: The property is best accessed from the back covered porch and instructions are provided in guest check-in details.brbrbrbrThe Neighborhood:brbrWelcome to Woodstock, Vermont, where storybook village charm meets fresh-air adventure at the doorstep. Set on a quiet dead-end street in the heart of Woodstock Village, 13 Golf Avenue sits directly across from the Mt. Peg trailhead, making it effortless to start your day with a hike and end it with a stroll to the Historic Woodstock Green. This beloved village is known for its beautifully preserved architecture, inviting boutiques, galleries, and bookstores, plus cozy cafés and standout restaurants that make wandering around town part of the vacation. Beyond the village, the landscape is pure Vermont—rolling hills, winding roads, and four-season beauty that feels like a postcard in every direction. With golf, fly fishing, and skiing all nearby, this is an ideal home base for a classic New England getaway.brbrbrbrThings to See & Do:brbr• Explore: Hike Mt. Peg From The Trailhead Across The Street, Stroll The Historic Woodstock Green, Visit Billings Farm & Museum, Walk The Village Shops And Galleriesbrbr• Covered Bridge Tours: Taftsville Covered Bridge, Quechee Covered Bridge, Middle Covered Bridgebrbr• Ski: Saskadena Six Ski Area, Killington Ski Resort, Pico Mountainbrbr• Award-Winning Golf Courses: Woodstock Country Club, Quechee Lakes Country Club, Green Mountain National Golf Course, Killington Mountain Coursebrbr• Museums: Billings Farm & Museum, Woodstock History Center, Vermont Institute Of Natural Science, Montshire Museum Of Science, Simon Pearce Millbrbr• Local Markets: Woodstock Farmers’ Marketbrbr• Local Restaurants & ShoppingbrbrRestaurants: Simon Pearce, The Skinny Pancake, Worthy Kitchen, Prince & The PauperbrbrShops: F. H. Gillingham & Sons, Woodstock Scoops, Local Boutiques And Galleries Around The GreenbrbrbrbrAnnual Festivals & Events:brbr• Wassail Weekend In Woodstockbrbr• Quechee Hot Air Balloon, Craft & Music Festivalbrbr• Vermont State FairbrbrbrbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!brbrbrbrVillage of Woodstock Rental Registration Number #brbrbrbrGetting Around:brbrCome and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of nearby Hanover, creating an unforgettable blend of outdoor adventure, historical exploration, and small-town charm. Whether you’re soaking in the scenic wonders, browsing village shops, or planning a day trip to Dartmouth, the Upper Valley promises a little something for every traveler. From Woodstock to Barnard and beyond, you’ll find endless opportunities for hiking, skiing, biking, and relaxed afternoons that feel quintessentially New England.brbrbrbrTraveling To/Around The Upper Valley Region Of Vermont — Explore By Foot, By Ski, By Bike, Or By Horseback:brbr• You’ll definitely need your own car, as there are limited taxis available. While the village itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car.brbr• Bike rentals are available in the village, though biking in the commercial area is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse more rugged areas.brbrbrbrAirports:brbr• Burlington (BTV) [VT]brbr• Lebanon (LEB) [NH]brbr• Manchester (MHT) [NH]brbr• Boston Logan (BOS) [MA]brbrbrbrPopular Landmarks:brbr• Mount Ascutneybrbr• Norman Williams Public Librarybrbr• Woodstock Town Hallbrbr• Marsh-Billings-Rockefeller National Historical Parkbrbr• Saint-Gaudens National Historic Sitebrbr• President Calvin Coolidge State Historic Sitebrbr• Alden Partridge Plaquebrbr• Joseph Smith Memorialbrbr• Whale’s Dancebrbr• Largest Zipper In North Americabrbr• Vermont Vietnam Veteran’s Memorialbrbr• Hanover, Home To Dartmouth UniversitybrbrbrbrInteraction with Guests:brbrOur goal is that your vacation exceed your expectations. Field & Farm Vacation Homes by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.brbrbrbrWe follow the CDC and Airbnb Recommended Cleaning Guidelines. You can rest assured this property has been completely sanitized prior to check-in.
Bed 3

Bed

Bath 2

Bath

Sleep 6

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Exceptional(60)

$525.45

/ Nightly
Private Vacation Home

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Woodstock, Vermont, United States

This exceptionally nice, renovated converted carriage house sits on a private 280 acre estate 2 miles from downtown Woodstock. All windows overlook undisturbed fields, mountains, and the Woodstock valley. It is completely furnished, has outside deck with beautiful views, a slate floor ski/mud entrance, a back entrance perfect for storing bikes, skis gear, and changing out of active wear, and doorstep parking. Convenient to several ski areas (Killington, Pico, Okemo, Suicide Six), downtown Woodstock, great restaurants, shopping, fishing, hiking, Mt. Tom and Rockefeller/Billings National Park Nearly abuts property), Quechee, and other scenic Vermont areas. The property road is one of the most sought after photographed spots in all of Vermont, many coming for the famed Sleepy Hollow photo op. Directly up the hill from us is the Cloudland Farm farm to table restaurant. Come enjoy the serenity of a visit to the Woodstock area.brProperty: The rental is a renovated Carriage House once used to house the horse caretaker. The rental is across the street from the Main House with plenty of privacy. The surrounding 280 acre property is private and undeveloped. There is a small farm with seasonal cows and farming. During the summer months cows graze some of the fields as well. There are multiple secluded ponds that can be fished for trout or to view deer, ducks, birds of prey and other wildlife. The property has miles of private hiking trails (subject to weather and season) as well as extensive gardens that have been featured in local publications as well as highly sought after by artist looking for landscape painting and gardening enthusiasts.brbrPlease read House Rules.
Bed 2

Bed

Bath 1

Bath

Sleep 4

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Exceptional(154)

$188.71

/ Nightly
Apartment

Charming Log Cabin Apartment in Woodstock Village

Woodstock, Vermont, United States

Escape to one of the prettiest towns in America. Make your vacation a quiet visit in a quintessential, charming apartment close to it all. We offer a ideal vacation rental: one bedroom log home apartment in the woods within walking distance of the Woodstock village center.brbrThe vacation rental apartment is 900 square feet and sleeps up to 4 people, 2 on a new queen sofa bed with tempurpedic mattress. There is a separate bedroom with queen bed. The full kitchen opens to the large living room with cathedral ceiling. Full size appliances include a brand new stainless steel refrigerator, stove, oven, dishwasher and both a washer and dryer. Enjoy cable, flat screen TV and wireless internet (WiFi). We do not permit smoking or pets.brbrThe apartment is a short, 1/4-mile walk to the heart of the village. We have wonderful shops, a beautiful library, several covered bridges, many highly-rated restaurants and a National Park.brbrTHINGS TO DO AND SEE: br- QUECHEE GORGE: 10 minutes awaybr- 4 top notch LIVE THEATERS within 20 minutes (2 in Woodstock) Opera and Balletbr- BILLINGS FARM AND MUSEUM: 5 minutes awaybr- Mt. Tom which overlooks the village is a national park, and there are 2 state parks within 20 minutes.br- 3 local BREWERIES: 15 minutes awaybr- PRESIDENT COOLIDGE'S BIRTHPLACE AND MUSEUM: 20 minutes awaybrbrMORE TO DO: br- The VERMONT INSTITUTE OF NATURAL SCIENCE within 10 minutes. It is a place for raptors to heal. Live demonstrations.br- King Arthur Flour home: 20 minutes awaybr- The athletic center includes tennis, pickleball, workout facility, pool: 2 minutes awaybr- The host coordinates pickleball on a daily basis, and would be happy to include guestsbr- DARTMOUTH COLLEGE AND VERMONT LAW SCHOOL a short drive.br- Buy your CHEESE where it's made: Sugarbush Farmbr- Woodstock has an indoor rink for ICE SKATINGbrbrFor last minute reservations, Bob can provide updated snow conditions for DOWNHILL AND CROSS COUNTRY SKIING, SNOW SHOEING AND SLEDDING within minutes of this property. Bob can also assist with dinner reservations.brbrThe second Saturday in December is WASSAIL WEEKEND. Check it out online and BOOK EARLY!
Bed 1

Bed

Bath 1

Bath

Sleep 4

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Exceptional(16)

$1438.21

/ Nightly
Private Vacation Home

Luxury Estate 25 Gorgeous Acres of Privacy Family Getaway Swimming Pond

Woodstock, Vermont, United States

Gorgeous family home on a 25-acre estate in a picturesque natural setting. Escape the bustle of city life.brbr ‍ ‍ ‍ Large, lush house that sleeps up to 8 people, with all the comfort and supplies of a family home. Enjoy the luxury of a crisp, immaculate, well-equipped home in a serene setting.brbr Nestled away in Woodstock, one of New England’s most precious gems, this spacious home is a safe haven for families looking to get away from the city. Surrounded by stunning greenery and nature, it’s the perfect retreat from the chaos.brbr With the picturesque character of a four-season New England town, this gorgeous home overlooks the striking Vermont countryside and Green Mountains.brbr The home is simultaneously secluded and only a 5-minute drive from the colorful, historic and pedestrian town of Woodstock.brbr ️Spacious and stocked kitchen for lavish and healthy dining with your familybrbr✨A private jacuzzi in the picturesque Vermont countryside. Is there a better way to forget the chaos of city life brbr The house is fully disinfected and stocked with cleaning supplies for your convenience.brbrThe space:brbr FIRST FLOOR Built for quality family enjoyment. Everyone can relax in the spacious living room and enjoy family time watching movies with all the premium channels around the cozy fireplace.brbrSteps away the family room is full of games to keep everyone entertained and having fun.brbr Enjoy warm meals cooked in a kitchen that would make the fussiest chef glow. The formal dining room is spacious, sun-lit and designed for a warm family feel, with seating for 8.brbr Need a break from humans This secluded home is an ideal natural getaway with the outdoor jacuzzi and barbecue, the home burrowed is in rolling greens and breathtaking natural views.brbr Spacious and sunny downstairs bedroom with full bathroom and luxury Brooklinen bedding, for a well-rested retreat. This is perfect for any family member that needs easier access.brbr SECOND FLOOR The rest and restoration space. Three huge, private bedrooms. The master bedroom has a regal en-suite bathroom and the finest, plush bedding for the king-size bed. brbrThe remaining two rooms are just as comfortable -- both with queen-sized beds and large windows overlooking calming nature.brbrThe second floor has an additional shared bathroom to comfortably accommodate every family member.brbr ADDITIONAL GUEST HOUSE AVAILABLE If you need a separate oasis for rest or restoration, we have a guest house separate from the main house available with room for 2 people. Please reserve this space in advance. This increases capacity to 10.brbrOther notes:brPlease note you are booking a home versus a hotel. Homes are imperfect. Not every window will be operational but plenty will, not everything will be curated in the way a hotel would be. brbrYou might see outdoor service people during your stay such as gardeners and we have entry point outdoor security cameras outside the front door and garage. No cameras are inside the home.brbrDogs welcome with pre-approval and $295 pet fee
Bed 4

Bed

Bath 2

Bath

Sleep 8

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$1072.4

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Private Vacation Home

Ski-In/Out to S6, Sauna & Hot Tub - Little House

Woodstock, Vermont, United States

Summary:brExperience true ski-in/ski-out luxury at the very top of Saskadena Six in Woodstock, VT, where a stunning, light-filled cottage awaits with soaring ceilings, chef’s kitchen, private hot tub, and glass-front sauna—just steps from the slopes. Unwind in unmatched comfort with chic mountain design, vaulted spaces, cozy fireplace, and an outdoor oasis perfect for après-ski relaxation and memorable mountain getaways.brbrPlease SEE: Other Things to NotebrFor Area Details, Please SEE: The Neighborhood & Getting Aroundbr*This is a no pet/animal home.brbrThe Space:brLittle House, Home Features:br• 2 Bedroom, 1 Bath - Available for up to 4 Guests!br• Private Hot Tub & Solo Stove Firepitbr• Outdoor Private Saunabr• Ski-in/Ski-out to S6!br• Free WiFibrbrWelcome to your ultimate ski-in, ski-out spa retreat, perched at the very top of Saskadena Six (S6) in Woodstock, VT. This beautifully finished 2-bedroom, 1-bath cottage not only puts you just 100 feet from where the S6 lift drops off—so you can step outside and ski straight onto the slopes—but also elevates your stay with luxurious amenities tailored for relaxation. Imagine ending each day with a soothing sauna session or a soak in your private hot tub, all amidst breathtaking mountain views. Whether it’s a romantic retreat, family ski weekend, or Vermont escape with friends, this cottage was designed for style, comfort, and memorable experiences. Arriving is easy, with convenient parking available right in front of the cottage. Once you pull in, simply head to the right to find the front door—no need to haul your gear through the snow. Settle in and enjoy the truly private, peaceful setting with outstanding mountain views.brbrInside, you’ll find a bright, airy open floor plan with vaulted ceilings and skylights filling the home with natural light. The spacious living area invites you to relax after a day outdoors, complete with a cozy electric fireplace to warm up beside during chilly Vermont evenings. The modern kitchen is a chef’s dream, featuring a stainless steel gas stove and hood, plenty of spacious counters for meal prep, and everything you need for home-cooked meals. Grab a seat at the kitchen island with comfortable bar stools for casual dining, breakfast, or to wind down with a glass of wine. Comfort is key throughout the cottage, with minisplit systems for personalized heating and cooling in each bedroom and the main living area—keeping you cozy in winter and cool in summer. The primary bedroom offers a queen bed, while the second bedroom—located just past the kitchen—has two twin beds. Both bedrooms are conveniently adjacent to the shared bathroom, which features a modern standing shower.brbrStep outside and enjoy your own private mountain oasis. Up a set of stone steps, you’ll find a stunning outdoor sauna hut with glass front doors, offering warmth and relaxation with amazing views. Unwind in the private hot tub, or gather on the patio, which includes both dining seating and comfortable chairs for lounging and meals outside. Near the hot tub, Adirondack chairs surround a Solo Stove firepit—perfect for evening conversations and stargazing. Every detail of the outdoor space invites you to relax, connect, and soak up Vermont’s beauty.brbrAlthough the cottage is tucked away in a serene hilltop setting, you’re only a short drive from the heart of Woodstock, with its charming shops, restaurants, and year-round attractions. If you’re searching for true ski-in, ski-out living at the top of S6, with amenities like a glass-front outdoor sauna, private hot tub, patio dining, fireside Adirondack chairs, your own cozy electric fireplace, a chef’s kitchen with stainless steel appliances, a kitchen island with bar stools, and an airy open floor plan with vaulted ceilings and skylights, this is the place to be. Book your stay or reach out with any questions—your unforgettable Vermont mountain getaway awaits.brbrGuest Access:brWe offer convenient door codes for self-check-in. Field & Farm Vacation Homes by Portoro uses convenient keyless entry for self check-in, details provided 2 weeks (or less) prior to arrival by email and text message.brbr• Early check-ins or late check-outs: If the property happens to be ready earlier than the standard 3 pm check-in time on the day of your arrival, in most cases an early arrival option may be available when confirmed with the main office. Late check-outs must be confirmed with main office staff prior to the date of departure.brbrThe Neighborhood:brWelcome to the enchanting Upper Valley, where Vermont's picturesque landscapes blend seamlessly with the cultural richness of Hanover, New Hampshire. Get ready to swoon over Woodstock, Vermont's charming hamlet. This historic village boasts stunning colonial and federal-style buildings that have been lovingly preserved for generations. It's the perfect spot for a dream vacation filled with architectural delights! Discover a collection of unique businesses that make this village extraordinary. From charming art galleries and quaint bookstores to specialty shops, cozy cafes, gourmet restaurants, and lively bars—there's always something delightful to explore! Beyond the allure of local activities, this property is set against one of New England's most stunning landscapes. Historical architecture and rolling hills combine to create a picturesque setting that captures the essence of Vermont's beauty. Located within 15 miles of three championship golf courses in Woodstock and Quechee.br brThings to See & Do:br• Explore: Take the Historic Covered Bridge Tour, Hike the Quechee Gorge,Whistlepig Tasting Room, Visit the Dream Alpaca Farmbr• Covered Bridge Tours: Quechee Covered Bridge, Taftsville Covered Bridge, Packered Hill Covered Bridge, Martins Mill Covered Bridge, Willard Twin Covered Bridges, Martins Mill Covered Bridge, Middle Covered Bridge, Waitsfield Village Covered Bridgebr• Ski: Saskadena Six Ski Hill, Killington Ski Resort, PICO Ski Resortbr• Award-Winning Golf Courses: Lakeland Golf Course, Highland Golf Course, Quechee Lakes Country Club, Woodstock Country Club, Green Mountain National, Killington Mountain Coursebr• Museums: Simon Pearce Mill, B.f. Southgate Antiques Collaborative, Glenn Suokko Gallery, The Ice House Museum, Vermont Institute of Natural Science, Billings Farm and Museum, Montshire Museum of Science, Hall Art Foundation, Old Windsor Constitution House, Woodstock History Centerbr• Local Markets: Jake’s Quechee Market, Quechee General Store - Cabot Stationbr• Local Restaurants & Shoppingbr- Restaurants: The Skinny Pancake, Public House Pub Quechee, Simon Pearce, Chef Brad’s CrazySide, Thyme Restaurant Vermont, Dewey’s at Quechee Club, Quechee Club, Soulfully Good Cafe, Au Comptoirbr- Shops: Quechee Gorge Village, The Vermont Spot, Quechee General Store - Cabot Station, Vermont Antique Mall, Fat Hat Clothing Company, Vermont Alpaca Store, Simon Pearcebr brAnnual Festivals & Events:br• Quechee Hot Air Balloon, Craft & Music Festivalbr• White Mountain Boogie and Blues Festivalbr• Vermont State FairbrWe provide a full list of Things to Do & See and local Restaurants & Shops to experience for our guests including in a personalized Guest Manual in your check-in details provided prior to your stay!br brVillage of Quechee Rental Registration Number #brbrGetting Around:brCome and make unforgettable memories in this charming Vermont haven. We welcome you! This Upper Valley experience seamlessly weaves together the natural beauty of Vermont with the cultural vibrancy of Hanover, creating an unforgettable blend of outdoor adventures, historical exploration, and small-town charm. Whether you're soaking in the scenic wonders or delving into cultural delights, the Upper Valley promises a journey for every traveler. Discover endless opportunities for adventure and relaxation in the Woodstock-Barnard area of Vermont, where every moment is infused with the essence of New England charm. Nestled amidst breathtaking natural beauty, our vacation rental offers unparalleled access to various attractions and activities that cater to every interest.br brTraveling to/around the Upper Valley region of Vermont - Explore by foot, by ski, by bike, or by horseback:br• You’ll definitely need your own car, as there are limited taxis available. While the town itself is walkable, it will be necessary to drive to nearby hikes and sightseeing spots. The outer parts of town, such as South Woodstock, are only conveniently accessed by car.br• Bike rentals are available in the village, though biking in the commercial area of the village is discouraged, as the flow of people and cars can be concentrated. The terrain has many hills, and a mountain bike should be used to traverse such rugged areas. br brAirports:br• Burlington (BTV) [VT]br• Lebanon (LEB) [NH]br• Manchester (MHT) [NH]br• Boston Logan (BOS) [MA]br brPopular Landmarks:br• Mount Ascutneybr• Norman Williams Public Librarybr• Woodstock Town Hallbr• Marsh Billings Rockefeller National Historical Parkbr• Saint Gaudens National Historic Sitebr• President Calvin Coolidge State Historic Sitebr• Alden Partridge Plaquebr• Joseph Smith Memorialbr• Whale’s Dancebr• Largest Zipper in North Americabr• Vermont Vietnam Veteran’s Memorialbr• Hanover, Home to Dartmouth UniversitybrbrInteraction with Guests:brOur goal is that your vacation exceed your expectations. Field & Farm Vacation Homes by Portoro communicates via email and phone. After a booking is confirmed, rental agreement will be emailed to the guest for e-signature. Check-in instructions are sent by email and text message 14 days (or less) prior to arrival date. We offer convenient keyless entry for self-check in. We do typically check in with guests by text 1-2 times during their stays to ensure a 5-star experience and remain available for any questions. We are available to guests 24/7 for any inquiries.brbrWe follow the CDC Recommended Cleaning Guidelines. You can rest assured this property has been completely sanitized prior to check-in.
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