Vacation Rentals By Owner In Chester, VT

Relax on the patio on the bank of the Williams River to watch the leaves turn, explore hiking trails, enjoy the outdoor fire pit, and mnt bike. Play soccer on indoor turf or corn hole in the rec room—half mi. from outdoor ice skating, disk golf, and VAST. Our three-bedroom home has one1 bunk room, two rooms overlooking the Williams River, and two full bathrooms- perfect for a family getaway. Enjoy grilling on the private back patio. brJust 15 minutes to Magic & 20 minutes to Okemo. The historic Town of Chester is an amazing destination to visit during the fall and winter months.

Riverfront, family fun, amazing rec room, close to Magic & Okemo

Chester, Vermont, United States

Bed

Bath

Sleeps

$166.05

Pet Friendly w/ Fee (Max 1) | Close to Hiking & Skiing | On-Site Goats | Foliage ViewsbrbrFrom crisp autumn mornings to snowy winter days and star-filled summer nights, the beauty of Vermont is yours to enjoy year-round at this cozy 2-bed, 1-bath vacation rental. On-site, wander the property's lush brookside grounds and wave hello to the adorable resident goats, then go for a scenic hike in Mt. Ascutney State Park or shred the slopes at Okemo Mountain Resort. The 'Getaway at Great Brook' awaits!brbr-- THE PROPERTY --brbrMRT-11153470-001brbrSLEEPING ARRANGEMENTSbr- Bedroom 1: 1 full bedbr- Bedroom 2: 1 full bedbrbrINDOOR FEATURESbr- Flat-screen TV, electric fireplacebr- Dining table, sunroombr- Mid-century furnishings, nature-themed decorbrbrOUTDOOR SETTINGbr- Deck w/ gas grillbr- Sun deck w/ lounge seatingbr- Peaceful brookside surroundingsbrbrKITCHENbr- Cooking basics, dishware/flatwarebr- 4-burner range, microwave, toasterbr- Drip & Keurig coffee makersbr- Complimentary coffee, tea, sugar, spices, oilbrbrGENERALbr- Free WiFi, washer/dryerbr- Linens/towels, complimentary toiletriesbr- Central heatingbr- Room-darkening shadesbrbrFAQbr- Pet fee (paid pre-trip, max 1)br- No A/CbrbrACCESSIBILITYbr- Single-story home, 4 stairs to enterbrbrPARKINGbr- Driveway (4 vehicles)br- RV/trailer parkingbrbr-- THE LOCATION --brbr- Orchards & sugar houses nearbybr- 7 miles to Chester shops & restaurantsbr- 10 miles to Okemo Mountain Resortbr- 17 miles to Mt. Ascutney State Parkbr- 28 miles to Rutland Southern Vermont Regional Airportbr- 135 miles to Boston Logan International Airportbrbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $150 fee (+ fees & taxes)br- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbrbrADDITIONAL INFORMATIONbr- This single-story home requires 4 stairs to enterbr- The property does not have air conditioning

Peaceful Brookside Getaway ~10 Mi to Okemo Slopes!

Chester, Vermont, United States

Bed

Bath

Sleeps

$344.28

Welcome to The Farmhouse of VT. Step back in time in this 1869 farmhouse, showcasing both antique rustic furnishings, combined with modern comfortability. The Farmhouse comfortably sleeps 8 people, across 5 beds.brbrYou are only:brbr- 10 mins to Grafton, Vermont (one of the prettiest villages in all of VT)br- 15 mins to Magic mountainbr- 20 mins to Okemo mountainbr- 30 mins to Bromley mountainbr- 40 mins to Killington mountainbrbrSkiers Paradise - after a day of hitting the slopes at one of the amazing ski mounts nearby, come back to the farmhouse, drop your skis, boots and coats in the mudroom; take a warm shower and walk down the street two doors to Pizza Stone! Open Thurs, Fri, Sat. with great pizza, live music, and a great craft beer menu. A three minute walk back to the house and hit the jacuzzi, to soothe those tired muscles, from a long fantastic ski day.brbrThe farmhouse has something for everyone!brbr- Ping Pong tablebr- Board Gamesbr- Puzzlesbr- Harry Potter Booksbr- Kids Room with drawing booksbr- Yoga Studiobr- Jacuzzi (I mean let’s be honest - is it a vacation without a jacuzzi )br- Outdoor Fire Pitbr- BBQ Grillbr- Outdoor activities (football, badminton set, horseshoes, croquet, cornhole)br- Cable TV (Don't miss a great football game!)br- Pianobr- NordicTrack Elliptical brbrPIZZA - 2 minute walk to a great local pizzeria/ bar. Open Thurs-Sat, with live music.brbrWIFI - the farmhouse wifi is laser fast! Fast wifi and an entire office space to work.brbrLIVING ROOM - Grab a warm coffee, from our fully-stocked coffee bar and lay down on the new living room couch, and enjoy the solitude of The Farmhouse. Or grab a blanket, throw on the TV and watch a movie. Access to any main streaming app (Netflix, HBO Max, Hulu, Amazon, etc.). Cable TV is included.brbrKITCHEN - Enjoy the fully-equipped kitchen with spices, olive oil, and all the equipment you would need to make a large dinner spread. Serve your food on the large antique farmhouse dining table, bringing a sense of old family dinner vibes to your evening.brbrBEDROOMS - In this four bedroom house, every bedroom is equipped with a brand new memory foam mattress. Close your eyes to a peaceful home, and recharge for the next day’s adventure.brbrOUTDOOR SPACE - Enjoy our peaceful backyard, sitting on 0.5 acres of land, surrounded by large mature trees and forest. Plenty of space to throw around the football, set up the badminton set, or just lounge around the fire pit. The garage is stocked with plenty of firewood for your group. brbrJACUZZI - In the evening, turn on the solar powered low lit string lights and take a soak in the brand new 7 person jacuzzi. This jacuzzi was installed in October, 2023. This jacuzzi is salt water operated, making it fantastic for your skin. Therefore, this isn’t just a jacuzzi, it’s your own personal rejuvenation spa. brbrYOGA STUDIO - this yoga studio is in our unfinished barn. Furnished with old farmhouse doors and windows left on the property. This old barn is not meant for kids, but is great for any adult looking to grab a yoga mat and recharge.brbrMessage me if you have any questions. I look forward to hosting you and your group's stay at The Farmhouse.

Agritourism

Rustic 150-year-old farmhouse, Jacuzzi includednn

Chester, Vermont, United States

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Bath

Sleeps

$577.29

Enjoy a historic stay in this former Chester Schoolhouse recently renovated into a massive yet cozy home. Located only 13 min away from Okemo Mountain and central to restaurants, shopping, hiking, and recreational activities. This unique property has parking for up to 5 cars, sleeps 7 comfortably, and has a spacious backyard for outdoor activities. Relax in the new 7 person hot tub, or make smores at the fire pit under a starry night!

UNIQUE/HISTORIC STAY IN AN 1874 ERA SCHOOLHOUSE!!

Chester, Vermont, United States

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Bath

Sleeps

$508.2

This home is located in the heart of the Stone Village in Chester and was built in 1844 by the Clark brothers. This is one of the Three Sisters homes that was built with beautiful local quarry glimmerstone in the Greek Revival stylings known to the area. This home has been tastefully renovated to maintain its original character while being updated for modern conveniences. Inside you will find ornate trim work, original wide plank flooring, breathtaking windows, and plenty of charm!brbrThis well-appointed 5 bedroom, 2 bath furnished home is perfect for your family vacation. Maximum of 8 overnight guests are allowed.brbrBedroom 1: Queen bed brBedroom 2: Queen bed brBedroom 3: Queen bed + 2 twins brBedroom 4: Full bed brBedroom 5: Full bed brbrPerfect getaway in the heart of Chester close to downtown shopping and restaurants. Limitless opportunities for outdoor activities like skiing, snowmobiling, hiking, canoeing, swimming, golfing, and more. 15 minutes to Okemo and close proximity to plenty more local, EPIC, and IKON mountains!brbrPerfect for a comfortable and convenient getaway in Vermont!brbrYou are renting in a quiet neighborhood. Please, no parties.brbrThis home is almost 200 years old. It has some quirks, but you will be blown away by the charm!

Spacious 5-bedroom Historic Stone House near Okemo

Chester, Vermont, United States

Bed

Bath

Sleeps

$418.72

Spacious, private and fully outfitted for a group getaway to Vermont, this 3-bedroom, 3-bath vacation rental is ready for 4 seasons of adventures! Set on 4 private acres with a wraparound deck for summertime relaxation, and a floor-to-ceiling stone fireplace for staying cozy in the winter, this Chester home ensures a stress-free stay. Numerous nearby state parks offer endless hiking and fishing, while Okemo Mountain Resort is under 10 miles away, and Killington is just 32 miles from the home!brbr-- THE PROPERTY --brbrMRT-11153470-001 | Ping Pong & Foosball | 2,700 Sq Ft | Free WiFi | ~10 Miles to SkiingbrbrIdeal for groups of friends and multi-generational families, this expansive home makes an ideal home base for launching mountain adventures and spending time together!brbrBedroom 1: Queen Bed | Bedroom 2: Twin Bed, Twin/Full Bunk Bed | Bedroom 3: Queen Bed | Living Room: Twin Sleeper LoveseatbrbrINDOOR LIVING: Vaulted ceilings, floor-to-ceiling stone fireplace, built-in shelves, 4-person table, laptop-friendly workspacebrOUTDOOR SPACE: Wraparound deck, Adirondack chairs, wooden porch swing, fire pit, spacious private yardbrKITCHEN: Fully equipped, stainless steel appliances, 2-person island, microwave, coffee maker, toaster oven, cooking basics, dishware & flatware, blenderbrREC ROOM: Ping pong table, 4-person table, seating area, flat-screen TV w/ Sling Blue Netflix & HBO Go/Now apps, yard accessbrGENERAL: Washer/dryer, iron/board, mudroom w/ ski racks and gear shelving, ceiling fans, suitable for children, suitable for elderlybrPARKING: Garage (2 vehicles), driveway (3 vehicles)brbr-- THE LOCATION --brbrWINTER REC: Okemo Mountain Resort (9.9 miles), Killington Ski Area (31.4 miles), Stratton Mountain Resort(29.6 miles), Magic Mountain Ski Area (17.3 miles), Mount Snow Grand Summit Resort (41.1 miles), Bromley Mountain Ski Resort (26.4 miles)brSUMMER REC: Fort At No 4 (12.5 miles), Wilgus State Park (16.9 miles), Mt Ascutney State Park (18.0 miles), Killington Ski Area (31.4 miles)brATTRACTIONS: Okemo State Forest (12.8 miles), Buttermil Falls (12.6 miles), Bromley Adventure Park (26.4 miles), Mt Ascutney State Park (18.0 miles), Saint-Gaudens National Historic Park (23.2 miles), Pillsbury State Park (39.1 miles), Mt Sunapee State Park (35.3 miles)brDINING: MacLaomainn's Scottish Pub (5.7 miles), the Pizza Stone (5.9 miles), The Hatchery (8.9 miles), Country Girl Diner (5.9 miles), Two Neanderthals Smokin' BBQ (5.5 miles)brAIRPORTS: Lebanon Municipal Airport (36.4 miles), Bradley International Airport (120 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties or large gatheringsbr- NOTE: Your safety matters. There is an exterior security camera, facing the driveway and main entrancebr- Please note all-wheel-drive car may be necessary to drive the 50-yard uphill driveway in the winterbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- This home's MRT ID # is MRT-11021438

Private Chester Home w/ Deck, Mins to Skiing!

Chester, Vermont, United States

Bed

Bath

Sleeps

$609.36

Maple Leaf Manor provides its guests with a comfortable stay in a renovated 1864 Brick Federal Style Farmhouse on 8 acres, as well as a true Southern Vermont experience in the heart of Chester, Vermont. brbrNestled on lovely grounds, this home is surrounded by natural beauty. The property is tucked away just 2 miles from town offering the perfect balance between seclusion and convenience. This property is ideally located being in close proximity to a variety of summer activities and everything that Vermont has to offer.brbrMaple Lead Manor consists of the following:brbrDOWNSTAIRSbrbr• Game Room with full size air hockey table and 75 Smart TV with soundbar and wireless subwoofer. Also includes retro stand up arcade game including classic 80s such as Galaga, Pac Man, Dig Dug, Mappy and more! Plus a large Connect 4, a large Jenga, and a beautiful wooden chess set. brbr• Laundry Room with washer and dryer. Fragrance free washer pods and dryer sheets provided.brbr• Kitchen with full amenities including microwave, air fryer, toaster, and air fryer. brbr• Den with reading library and 65 Smart TV with soundbar and wireless subwoofer. Also includes a pull out couch. brbr• Bathroom with clawfoot tub and bath salts and bath balls provided for those hot soaking moments after a long day on the mountain. brbr• Dining Room that seats 8. Leafs are available to increase the table to 10. brbr• Coffee Bar that included a Keurig and Drip Coffee Maker. Variety of coffees from Vermont's own GreenMountain Coffee Company.brbr• Living Room that consists of two sitting areas and a pellet stove. Guests have access to the pellet stove which is perfect after a long day on the mountain.brbr• Outdoor dining patio with seating for 8brbr• Jacuzzi with seating for 4. Towels provided. brbr• Pack and play and high chair available.brbrbrUPSTAIRSbrbr• The Maple Room - King Bed with dresser, bench, closet and extra pillows and blankets. Includes fresh bed linens, quilt, comforter and 4 pillows (two soft and two memory foam). Plus two extra pillows (one soft, one firm), extra quilt, and an extra comforter. Also includes a luggage rack for your suitcase. brbr• The Burgundy Room - Queen Bed with dresser, bench, closet and extra pillows and blankets. Includes fresh bed linens, quilt, comforter and 4 pillows (two soft and two memory foam). Plus two extra pillows (one soft, one firm), extra quilt, and an extra comforter. Also includes a luggage rack for your suitcase. brbr• Sage Room - Queen Bed with PRIVATE BATHROOM and SHOWER. Also includes dresser and bench. Includes fresh bed linens, quilt, comforter and 4 pillows (two soft and two memory foam). Plus two extra pillows (one soft, one firm), extra quilt, and an extra comforter. Also includes a luggage rack for your suitcase. brbr• The Twin Room - Two Twin beds with dresser, closet and extra pillows and blankets. Includes fresh bed linens, quilt, comforter and 4 pillows (one soft and one memory foam for each bed). Plus two extra pillows (one soft, one firm), extra quilt, and an extra comforters. Also includes a luggage rack for your suitcase. brbr• Full bathroom with shower and amenities including shampoo, conditioner, and body wash.brbrACCESS TO MOUNTAINSbrbr• 10 mins to Grafton, Vermontbr• 20 mins to Magic Mountainbr• 25 mins to Okemo br• 30 mins to Bromleybr• 45 mins to Strattonbr• 50 min to Killingtonbr• 50 min to Mount SnowbrbrPROPERTY ACCESSbrbr• Guests have access to the entire home including laundry room and jacuzzi. br• The Garage is NOT accessible.br• The Barn is NOT accessible at this time.br• Sorry, NO PETS.br• Ring camera installed at front door for security purposes.

Maple Leaf Manor - 1864 Brick Federal Style Farmhouse with a modern touches.

Chester, Vermont, United States

Bed

Bath

Sleeps

$326.4

Country Riverside RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrNestled just a short distance from the charming center of Chester, VT, this 1840 farmhouse exudes character and charm at every turn. With wide plank pine floors, original doors, and moldings, this home offers a cozy retreat for those looking to experience a piece of history. Step inside and be greeted by an inviting front porch that leads you into a country kitchen featuring a Viking range, built-in shelving, and a wood-burning stove perfect for those chilly winter nights. brbrOn the first floor, you'll discover a cozy den ideal for a home office, a beautiful formal dining room, and a spacious living room with a classic wood-burning fireplace (not for guest use) and access to the backyard stone patio. Upstairs, two bedrooms, a common space, and a second full bath await, offering comfort and relaxation for all guests. brbrSituated on 16.5 acres separated by Grafton Rd, the property boasts approximately 5 acres on the house side with a lovely meadow, privacy, and an impressive 800 ft of frontage on the south branch of the Williams River. Enjoy the serene riverfront setting and take in the picturesque views from the comfort of your own home.brbrConveniently located near major ski areas, town amenities, and with easy access to Rt 91, this home offers the perfect blend of tranquility and accessibility. Whether you're looking to explore the outdoors or simply unwind in a peaceful setting, this Chester farmhouse is the ideal destination for your Vermont getaway. Book your stay today and create unforgettable memories in this historic gem!brbrParking notes: There is free parking available for 3 vehicles.brbrbrbrDamage waiver: The total cost of your reservation for this Property includes a nightly damage waiver fee, plus tax if applicable (the “Damage Waiver”). (A discount may be applied for stays of 28 nights or longer, if permitted.) The Damage Waiver covers you for up to $3,000 of accidental damage to the Property or its contents (such as furniture, fixtures, and appliances) as long as you report the incident to the host prior to checking out. The Damage Waiver fee eliminates the need for a traditional security deposit.brMore information can be downloaded from the Rental Agreement on the checkout page.brbrDue to local laws or HOA requirements, guests must be at least 25 years of age to book. Guests under 25 must be accompanied by a parent or legal guardian for the duration of the reservation.

Charming farmhouse, riverfront, views, woodstove, w/d, wifi, TV, kitchen, deck

Chester, Vermont, United States

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Bath

Sleeps

$776.49

Lovingly updated antique 6 bedroom home in the historic Stone Village of Chester, VT. Sleeps 8+ comfortably making it the perfect vacation home for 1 or 2 families. brbrMain stone house was built in 1833 as an addition to the 1798 farmhouse. Combined it creates a classic Vermont home with 6 bedrooms and 3 full baths (includes 1st floor bedroom with en suite full bath). 3 living rooms with working fireplaces, comfortable seating for conversation and laughter, and beautiful artwork. Screened fieldstone floor side porch to pass the evening. Tuned piano for the musician in the yellow living room. Formal dining room that seats 10, plus a farmhouse kitchen with table that seats another 10, (great for the kids). Home is decorated with period antiques. brbrAttached via the kitchen, the renovated barn has a large family room with new wood burning stove, cozy seating, flat screen tv with Bose surround sound, smart TV for streaming Netflix, etc, 100 dvd movie collection huge game and puzzle closet, and beautiful view to the back yard and neighboring fields. brbrAdditional new electric wall heat/AC units in family room and each bedroom makes it easy to heat or air condition. Sliding doors open to stone patio with gas grill and large fire pit, festive lighting, outdoor speakers, with quality seating to gather around. brbr2 bedrooms and full bath await you on the 2nd floor of the barn. brbrComfortable well equipped kitchen has all your cooking essentials, plus, plus: blender, cuisinart, crock pot, up to date spices, oils, vinegars. Large variety of quality pans and every tool under the sun. If you like to cook you will be right at home. New washer and dryer in kitchen. A little quirky, but it's very convenient. brbrNew Ping Pong, Dart board, and Foos Ball table in the barn’s renovated playroom with new dry bar, including Sub Zero beverage fridge, Sonos speakers and heat/AC.brbrProperty sits on cleared 2 acres of land, with beautiful sunsets and open space to run around, throw a ball or play some frisbee.brbr Easy 1/2 mile walk - on a sidewalk, to a convenience store and terrific butcher. brbrThe home is located in Chester VT, a true treasure of a town with lots of conveniences. Lovely small town that is home to great restaurants, a Scottish pub, a delicious bakery for fresh bread and an out of this world pie shop, gourmet pizza restaurant with live music, knitting and quilting shops, art and furniture stores, a good sized bookstore, a couple of inns and large antique stores. 1 mile away from home is the pinnacle, the town of Chester's recreation area. In winter, it's a great sledding hill with a new well maintained outdoor ice skating rink. In Summer, it offers a skate park, frisbee golf, basketball, tennis, baseball field, pickle Ball, and town swimming pool.brbrEasy access to Weston Playhouse for high quality summer theater, hiking, Okemo golf resort, and Tater Hill Golf. Four Frisbee golf courses within 10 miles, Buttermilk Falls for hiking and cooling off. Okemo (straight 20 minute drive up route 103), Magic Mountain (20 minutes down Rt 11) or Bromley, and Stratton mountains nearby. brbrSingle dog over the age of 1 welcome. Sorry no cats or other critters. brbrArticle on the historic stone villagebrhttps://www.onlyinyourstate.com/vermont/tiny-village-vt-2/

Luxury stone farmhouse.Perfect for families or company retreats! Close to Okemo!

Chester, Vermont, United States

Bed

Bath

Sleeps

$342.72

Rest, relax, and enjoy the tranquil surroundings when you visit this vacation rental home in Chester, Vermont! The stunning house has 4 bedrooms, 3 bathrooms, and boasts exposed beams, wall-to-wall windows, and vaulted ceilings. Complete with an immaculate yard, the property features a private swimming pond ideal for cooling off in the summer! Spend fall days admiring the changing leaves and hit the nearby slopes come winter. This perfect all-season getaway has everything you need!brbr-- THE PROPERTY --brbr* NOTE: Guests must follow the State of Vermont quarantine regulations prior to their arrival. The regulations can be found on the Vermont Department of Health website * brbrMRT-11153470-001 | Wooded Views | Outdoor Living Space brbrPerfect for families, this spacious and welcoming home in Chester is comfortably furnished and boasts amenities sure to entertain everyone! brbrBedroom 1: King Bed | Bedroom 2: King Bed | Bedroom 3: King Bed | Bedroom 4: Full Bed, Twin Bed | Additional Sleeping: Queen Air Mattress, Twin Air MattressbrbrOUTDOOR LIVING: Private swimming pond, outdoor dining table, covered patio, rocking chairs, fire pit, seasonal deck & gas grill (unavailable in winter)brKITCHEN: Fully equipped, coffee maker, dishware, flatware, 4-person breakfast bar, crockpot, basic cooking spices brINDOOR LIVING: Smart TV, 2 flat-screen TVs, fireplace, stereo, music collection, 8-person dining table, heated floors (first floor) brGENERAL: Free WiFi, washer/dryer, linens/towels, complimentary toiletries, hairdryerbrFAQ: 4WD recommended, no A/CbrPARKING: Gravel driveway (6 vehicles)brbr-- THE LOCATION --brbrSKI RESORTS: Magic Mountain Ski Area (17.2 miles), Bromley Mountain Ski Resort (26.3 miles), Okemo Mountain Resort (9.9 miles), Stratton Mountain Resort (32.1 miles), Viking Nordic Center (18.9 miles) brOUTDOOR RECREATION: Lowell Lake (16.6 miles), Herrick's Cove (16.7 miles), Bellows Falls Country Club and Golf Course (12.4 miles) brHISTORIC SITES: President Calvin Coolidge Homestead (20.6 miles), Hildene - Lincoln Family Home (36.8 miles), Saint-Gaudens National Historical Park (23.1 miles) brAIRPORT: Manchester Boston Regional Airport (92.7 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- No pets allowedbr- No events, parties, or large gatheringsbr- Must be at least 25 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The back deck and gas grill are unavailable in the winter monthsbr- NOTE: The property does not offer A/Cbr- NOTE: Your safety matters. This property features 2 exterior security cameras, located above the backyard and front yard, all facing outward. They do not look into interior spacesbr- NOTE: Guests must follow the State of Vermont quarantine regulations prior to their arrival. The regulations can be found on the Vermont Department of Health websitebr- NOTE: 4-wheel drive or all-wheel drive is highly recommended in the winter months to access the property

Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort!

Chester, Vermont, United States

Bed

Bath

Sleeps

$260.0

Sportsman themed, real log cabin that has comfortable wood stove & hearth, plus backup regular heat. Bathroom with shower for two and upstairs standable loft with a queen and full double bed. Plus one day bed cot & inflatable-single twin, w/pump. Upstairs & downstairs HD Smart TV/DVD player setups, plus internet service. Funky front porch with rocking chairs and beautiful gazebo for dining when not using the mini-great room's picturesque, view dining room table. Privacy plus, located on nice, quiet, town maintained gravel road. Over 100 free-use good DVD movies for your viewing pleasure. Small kitchenette with double sink, full size refrigerator and four burner gas stove with oven, plus microwave and pantry. All utensils and pots, pans, plates, cups & glasses included. You MUST bring your own linens (bedsheets & towels) &/ or sleeping bags. Blankets & quilts are available. Absolutely No Pets (sorry). No garbage pickup, so you Must remove any trash you create (plastic bags are provided). Brooms and vacuums provided for light self-cleaning before departure. Call Emergency 911 on your cell phone for EMT/Fire service in town. Installed landline phones are not connected and working currently. br Nearest hospital is in Springfield, VT, about 18 miles away.

Cabin

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

Chester, Vermont, United States

Bed

Bath

5

Sleeps

$344.9

Experience 180 degrees mountain views at this quaint farmhouse. World Class Skiing at Okemo Mountain is just 23 mins, Bromley is 30 mins, Magic Mountain is 17 mins and Stratton is only 25 miles away. Gather with friends and family and enjoy the large open living-dining room. This spacious mountain home boasts 4 large bedrooms in the 2nd floor and a quaint loft on the 3rd floor. Wake up with the breathtaking views of the mountain. Enjoy a cup of coffee at the outdoor porch and relax in our outdoor cedar barrel sauna. EV car charger is also available in the garage. The kitchen is well equipped with your cooking needs.

Agritourism

Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR

Chester, Vermont, United States

Bed

Bath

Sleeps

$201.6

Our Carriage House is less than a mile to charming Chester Village-enjoy quaint restaurants and taverns, antique shops, art galleries and a country market.brbrExplore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers and breweries (near Harpoon & Long Trail)brbrClose proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington)brbrCome experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!brbrOur quaint and cozy Carriage House, which once held horses in the 1880's is located in Okemo Valley and is perfect for city dwellers looking for a country escape, traveling families, romantic getaways, retreat weekends, girls trips, holiday stays, reunions, celebrations etc;brbrOur beautifully appointed space will make for a relaxing and peaceful getaway.brbr*Please note the main living areas (dining, kitchen, bedrooms, bathroom) are located on the second floor of the converted barn. There is a flight of stairs from entryway to living areas*brbrThe Carriage House offers 3 bedrooms each with luxurious queen memory foam mattresses. It comes equipped with full kitchen amenities for preparing fresh meals from the local farmer's market or general store across the street. We provide fresh ground coffee, creamer and assorted teas. There's even a laundry room! We are also happy to provide a Pack and Play, high chair and baby gates for those traveling with little ones.brbrFor Spring and Summer fun- take a hike! There are several popular hiking trails in Chester-Lost Mine Hiking Trail and Green Mountain Nature Trail. In Chester there is a town pool you can access or check out Buttermilk Falls in Ludlow for waterfall/swimming adventures. In Springfield there is a pick your own farm-Wellwood Orchards for strawberries, blueberries, raspberries, peaches, plums and cherries. For more outdoor adventures, bring your bikes, kayaks or golf clubs!brbrFall is a time of wonder and delight in this quintessential Vermont town-perfect for leaf peeping, picnicking, apple picking, scenic train rides at Chester Depot (only footsteps away from Elm House) or enjoy the annual fall festival on the green in September.brbrIn the Winter months, bring your ice skates, skis, snowshoes and snow boards! We are conveniently located near 5 of Vermont's finest ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington)brbrAnytime of the year is a great time to visit a maple sugar house, Mitch's Maples (less than a mile from our home) or the Vermont Country Store (less than 10 miles) or take a driving tour of Vermont's many covered bridges!brbrBe sure to check out the local dairy farm, Jersey Girls Dairy & Farm Store for fresh milk and dairy products or the nearby Farmers Markets in Ludlow and Londonderry.brbrFor a more relaxing and rejuvenating adventure, spa services are available at Castle Hill Spa-an Aveda Concept Spa.brbrThe Spring House Pool and Fitness Center at Okemo is another great place to unwind after a long day. Indoor pool, hot tub and fitness center.brbrDISTANCE FROM CARRIAGE HOUSE TO:brGrafton Inn-8 miles (12.8 km)brMagic Mountain Ski Area-13 miles (20.9 km)brOkemo Mountain Resort-15 miles (24 km)brBromley Ski Resort-22 miles (35.4 km)brStratton Mountain Resort-26 miles (41.8 km)brKillington Resort-29 miles (46.6 km)brWoodstock, VT-31 miles (49.8 km)brManchester, VT-31 miles (49.8 km)brManchester-Boston Regional Airport-Manchester, NH (MHT)-93 miles (149.6)brBradley International Airport-Hartford, CT (BDL)-114 miles (183.4 km)brBoston, MA-136 miles (218.8 km)brNew York City-249 miles (400.7 km)brbrPlease note:br**There is a glitch on VRBO showing pool, hot tub, gym-we do not have these items, nor have them selected as an option**brbrWe don't live on the property, but we have a caretaker nearby who can assist if needed. If an issue arises, please contact us right away so that we can solve it and you can relax + enjoy your stay!brbrWe're only a text or phone call away!brbrYou will find that cell phone service is sporadic in this southern region of Vermont-the Carriage House has a landline phone and long-distance service. (US & Canada)brbrIn Summer months-we have a window unit AC-we do not have central air.

Guest House

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

Chester, Vermont, United States

Bed

Bath

Sleeps

$317.37

Welcome to 'Smokeshire Hilltop Farmhouse!' This lovely 5-bedroom, 2-bathroom vacation rental sits on a plateau above the Williams River in Chester. Located on a working farm with beautiful grounds, the rustic farmhouse offers travels the ideal escape at any time of the year! Spend your day hiking the nearby trails in the summer or skiing the slopes at Okemo in the winter. After your adventures, cozy up by the wood-burning fireplace and enjoy a peaceful evening at home.brbr-- THE PROPERTY --brbrMRT-11153470-001 | Pet Friendly w/ Fee (Dogs & Horses Only) | Furnished Sunroom | Sleigh/Carriage Rides AvailablebrbrBedroom 1: Queen Bed | Bedroom 2: Full Bed | Bedroom 3: Queen Bed | Bedroom 4: 2 Twin Beds, Full Bed | Bedroom 5: 2 Twin Beds | Study: Sleeper SofabrbrOUTDOOR SPACE: Spacious unfenced yard, outdoor diningbrINDOOR LIVING: Flat-screen TV, DVD player, fireplace, dining table, shower/tub combobrKITCHEN: Stove/oven, microwave, dishwasher, refrigerator, dishware/flatware, toaster, spices, Keurig single-serve coffee maker, drip coffee maker, kettle, standing mixerbrGENERAL: Free WiFi, washer/dryer, linens/towels, central heating, mini-split A/C & heating unitsbrACCESSIBILITY: 2-story home, stairs required, 1 bedroom on 1st floorbrFAQ: Pet fee (paid pre-stay), 1 exterior security camera (facing front entry), 4WD recommended in winter, homeowner on-site (private home, same property), limited cell servicebrPARKING: Driveway (5 vehicles)brbr-- THE LOCATION --brbrWINTER REC: Okemo Mountain Resort (8 miles), Magic Mountain Ski Area (18 miles), Bromley Mountain Ski Resort (29 miles), Killington Ski Area (30 miles), Stratton Mountain Resort (32 miles), Mount Snow Grand Summit Resort (46 miles)brSUMMER REC: The Fort At No 4 (17 miles), Wilgus State Park (20 miles), Mt Ascutney State Park (21 miles), Killington Ski Area (30 miles)brATTRACTIONS: Okemo State Forest (11 miles), Buttermilk Falls (11 miles), Mt Ascutney State Park (21 miles), Saint-Gaudens National Historic Park (27 miles), Pillsbury State Park (42 miles), Mt Sunapee State Park (40 miles)brAIRPORTS: Lebanon Municipal Airport (40 miles), Bradley International Airport (122 miles)brbr-- REST EASY WITH US --brbrEvolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.brbr-- POLICIES --brbr- No smokingbr- Pet friendly w/ $50 fee (+ fees & taxes, dogs & horses only)br- No events, parties, or large gatheringsbr- Must be at least 28 years old to bookbr- Additional fees and taxes may applybr- Photo ID may be required upon check-inbr- NOTE: The 2-story property requires using stairs to enterbr- NOTE: This house is located on a working farm and animals may be present during your staybr- NOTE: Four-wheel drive or all-wheel drive is recommended in the winter months to access the propertybr- NOTE: The property does have cell phone service, but it may be spotty since the property is located in a rural area. Please check with your provider to confirm your service quality. There is a landline in the propertybr- NOTE: Your safety matters. This property features an exterior security camera located at the front door facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video and sound when motion is detected by the devicebr- NOTE: The homeowner lives on-site, in a completely separate unit, and may be present during your stay

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Chester, Vermont, United States

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$543.97

This incredible log home is the perfect spot for a weekend getaway or an extended stay in Vermont. Nestled on 6 acres of beautiful mountain-view land, this 4 bedroom home gives you all the amenities you need and more. Wake up each morning to the fresh air and rolling hills, and catch some restful sleep surrounded by serene nature. Gather with friends and family around the cozy fire-place - whatever you choose to do, enjoy every moment in this perfect oasis. With plenty of activities nearby as well, it's easy to make lasting memories here. Come experience true relaxation amongst nature at its finest!

15 Minutes to ski Okemo - Mountain views from this magical log home on 6 acres

Chester, Vermont, United States

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$1071.84

Nestled in the heart of the majestic Green Mountains, this charming 4-season retreat offers 12-acres of stunning views, modern comforts, and a peaceful atmosphere. Our cabin is ideal for families, couples, or anyone looking to unwind in nature.brbrAdd us and tag us @whiskicabinvt for photos, shoutouts, local recommendations, and more!brbrThis tranquil 2 story home has plenty of space to comfortably sleep 12 people with its 3 bedrooms and a bonus room with 2 full-sized baths. brbrFloor 1:br1 bedroom with 1 queen bed brbr1 bedroom with 2 full bunk bedsbrbr1 full-size bathroom with bathtub brKitchen - fully stocked with kitchen essentials , spices, dishware/flatware, dishwasher, refrigerator, stove, microwave, coffee maker, toaster oven, and ice maker brDining RoombrLiving Room (smart TV)brbrFloor 2:br1 Bedroom with 2 queen bedsbrBonus Room with 1 queen bed (smart TV)br1 full-size bathroom with bathtubbrbrWhile the house is officially listed for 3 bedrooms, we have ample space and comfortable arrangements for extra guests. We aim to provide a pleasant and accommodating stay for larger groups or families traveling together.brbrImportant Notes:brPlease note that our home is serviced by a septic system, and we kindly ask all guests to be mindful of water usage and waste disposal.brLocal regulations may limit the number of guests, so please confirm the maximum occupancy when booking.brbrOutdoor space: spacious deck with propane grill and a mountain view! brbrAmenities: High speed WiFi, Washer/Dryer, central air/cooling, heated garage access, ski racks in garage, parking on site, stainless steal appliances, board gamesbrbrTo ensure your stay is hassle-free, we include complimentary plowing and sanding services. Our trusted plowing team will clear the driveway and deck after every snowfall of more than 2-3 inches. brbrWhile our plowing service ensures easy access, we still recommend a 4WD vehicle during the winter months for the driveway, as well as navigating the road in which we are located. brbrIn Vermont, the winter weather takes its toll on road surfaces, causing wear and tear. Every May, the road the house is located on is re-surfaced with material to rejuvenate the surface. brbrThere are shovels located in the garage if you need during your stay. brbrWe’ve made it easy for you to store your ski gear safely and without hassle. Our secure ski racks, located in the heated garage, ensure your skis and snowboards are well-protected and ready for your next run down the slopes.brbrAll remote access with keyless entry for maximum guest convenience!brbrRight in your backyard, we offer 12-acres of wooded area that is yours to hike! There are orange markers leading you up and down the property, for your convenience brbrLocated close to multiple ski resorts:brOkemo - 15 minsbrKillington - 40 minsbrStratton, Bromley - 40 minsbrSunapee - 50 mins brbrCentral to surrounding towns for sightseeing and shopping:brSpringfield - 10 minsbrLudlow - 15 minsbrWindsor - 35 minsbrManchester - 45 minsbrBrattleboro - 45 minsbrWoodstock - 45 minsbrWeston - 45 mins brClaremont - 45 mins brbrDisclosure: We prioritize the safety and security of our guests and the property. To enhance security, we have installed Ring cameras in certain areas on the exterior of the the property. Cameras are NOT located inside the house as to respect your privacy during your stay.brbrA detailed welcome guide is provided when you arrive to help you settle in quickly!

WhiSki Cabin - 12 Acres With a Mountain View!

Chester, Vermont, United States

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Sleeps

$178.08

Enjoy a private room, bathroom & shower in the historic Chester Inn, circa 1780. This charming property is conveniently located on Main Street in walking distance to restaurants, shops & galleries.brbrPublic hiking /snowshoeing trails can be entered right through the backyard & Okemo mountain is just a short drive away!brbrAlthough the building is bed & breakfast style we do not provide breakfast.brbrRoom #4 is located on the second floor and contains the only jacuzzi tub on premises. This quaint room has bathrobes, a TV, mini fridge, coffee maker, mugs/wine glasses & bathroom essentials (Fireplace is currently not working). Shared spaces are available for reading, relaxing, watching TV, getting your coffee fix or enjoying board games. There is also a front porch available for your leisure.brbrGuests are free to access:br- Living roombr- Dining roombr- Kitchenettebr- Patiobr- Porchbr- Access to trails via backyard...brbrEstimated driving distance to popular skiing / snowboarding / tubing destinations:br- Magic Mountain - 15 minutesbr- Okemo - 19 minutesbr- Stratton - 31 minutesbr- Killington - 39 minutesbr- Mt. Snow - 50 minutes

Bed & Breakfast

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester, Vermont, United States

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$279.82

OVERVIEWbrOur historic 1868 'Elm House' is located in the picturesque town of Chester, nestled in the heart of Chester Depot. The 'Elm House' is perfect for city dwellers looking for a country escape, traveling families, romantic getaways, retreat weekends, girls trip, holiday stays, reunions, celebrations etc; brbrOur beautifully appointed and spacious space will make for a relaxing and cozy getaway. The Williams River flows behind our home amongst the chestnut and apple trees.brbrKITCHENbrOur home has a traditional farmhouse style kitchen complete with rustic wood floors and modern amenities. We have provided everything you need to prepare your own farm-to-table dinner with fresh food from the local farmer's market or country store across the street. We also have a Keurig and french press. For your added convenience we have provided a starter supply of fresh ground coffee, creamer and assorted teas.brbrDINING ROOMbrIn the formal dining room, we have a designated bar area equipped with glassware and other bar essentials as well as a full china set for your use.brbrBEDROOMSbrThe 'Elm House' offers 4 bedrooms, each designed to provide a relaxing and cozy atmosphere. Each bedroom is furnished with memory foam queen beds. There is one bedroom and bathroom on the first floor and three guest bedrooms and 1.5 bathrooms on the second floor.brbrWIFI & TVbrThe house has WIFI and a 'Smart TV' (Netflix, Hulu, Amazon, etc. streaming for your devices). brbrDECK & YARD AREAbrOutside, there is a large wraparound deck with rocking chairs where you can enjoy coffee or cocktails. The yard space has plenty of room for a picnic or for yard games.brbrMUDROOM/SKI STORAGEbrThere is also a large mudroom that is perfect for ski and snowboard storage.brbrWHAT TO DO:brIn the village of Chester-enjoy quaint restaurants and taverns, antique shops, art galleries, and a country market.brbrExplore southern Vermont’s famous hiking trails, world class skiing, farms, winding rivers and breweries (near Harpoon & Long Trail)brbrClose proximity to the best of Vermont's ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington)brbrCome experience why Chester has been voted one of the top 10 most beautiful towns in Vermont!brbrFor Spring and Summer fun- take a hike! There are several popular hiking trails in Chester-Lost Mine Hiking Trail and Green Mountain Nature Trail. In Chester there is a town pool you can access or check out Rainbow Rock (a local swimming hole) or Buttermilk Falls in Ludlow for waterfall/swimming adventures. In Springfield there is a pick your own farm-Wellwood Orchards for strawberries, blueberries, raspberries, peaches, plums and cherries. For more outdoor adventures, bring your bikes, kayaks or golf clubs!brbrFall is a time of wonder and delight in this quintessential Vermont town-perfect for leaf peeping, picnicking, apple picking, scenic train rides at Chester Depot (only footsteps away from Elm House) or enjoy the annual fall festival on the green in September.brbrIn the Winter months, bring your ice skates, skis, snow shoes and snow boards! We are conveniently located near 5 of Vermont's finest ski resorts! (Magic Mountain, Bromley, Stratton, Okemo and Killington)brbrAnytime of the year is a great time to visit a maple sugar house, Mitch's Maples (less than a mile from our home) or the Vermont Country Store (less than 10 miles) or take a driving tour of Vermont's many covered bridges!brbrBe sure to check out the local dairy farm, Jersey Girls Dairy & Farm Store for fresh milk and dairy products or the nearby Farmers Markets in Ludlow and Londonderry.brbrFor a more relaxing and rejuvenating adventure, spa services are available at Castle Hill Spa-an Aveda Concept Spa.brbrThe Spring House Pool and Fitness Center at Okemo is another great place to unwind after a long day. Indoor pool, hot tub and fitness center.brbrWe don't live on the property, but we have a caretaker nearby who looks after our home and can assist if needed. If an issue arises, please let us know immediately so we can solve and you can relax + enjoy your stay!brbrDISTANCE FROM ELM HOUSE TO:brGrafton Inn-8 miles (12.8 km)brMagic Mountain Ski Area-13 miles (20.9 km)brOkemo Mountain Resort-15 miles (24 km)brBromley Ski Resort-22 miles (35.4 km)brStratton Mountain Resort-26 miles (41.8 km)brKillington Resort-29 miles (46.6 km)brWoodstock, VT-31 miles (49.8 km)brManchester, VT-31 miles (49.8 km)brManchester-Boston Regional Airport-Manchester, NH (MHT)-93 miles (149.6)brBradley International Airport-Hartford, CT (BDL)-114 miles (183.4 km)brBoston, MA-136 miles (218.8 km)brNew York City-249 miles (400.7 km)brbrPlease note: br**There is a glitch on VRBO showing pool, hot tub-we do not have these items, nor have them selected as an option**brbrCell service is sporadic in this region of southern Vermont. Cell phone + GPS services may be limited in certain areas.brbrIn Summer months-we have window unit AC's in the bedrooms-we do not have central air.brbr

Circa 1868 Chester Home-Less than 20 MIN TO OKEMO

Chester, Vermont, United States

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Sleeps

$287.72

Welcome to Zen of the Woods! A cozy, thoughtfully designed tiny cabin retreat minutes from Okemo. Set amongst hundreds of acres of forest and farmland, find peace as you enjoy your morning coffee on the front porch overlooking the landscape. Take a walk in the woods out your front door. Enjoy the peace and solitude and unplug, or utilize the fiber optic high speed internet to work remotely in a beautiful setting! 15 minutes to Ludlow, 10 to the quaint villages of Chester and Proctorsville. Enjoy the outdoor shower in summer!

Cabin

Zen of the Woods Tiny Cabin in Okemo Valley

Chester, Vermont, United States

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