Vacation Rentals By Owner In Pittsfield, VT

| Welcome to The Skyeburst House | brbrReimagined 1970's Mountain Home 15 mins from the Killington K1 Gondola. This is a newly renovated modern home boasting lots of natural light, spa like bathrooms, open floor plan, and exposed cathedral ceilings. Curated with a mix of rustic and modern decor. High quality king and queen beds. Modern appliances. Samsung 75 QLED 4K TV. Sonos Sound System. Fire pit. Deck. Grill. Stars. Your Vermont adventure awaits.

3-bedroom house in lovely Pittsfield close to wedding venues, trails and skiing!

Pittsfield, Vermont, United States

Bed

Bath

6

Sleeps

$265.02

POWDER RUN: SMART 3BR BASECAMP W/ HOT TUB, AC, EV CHARGER & FLAT PARKINGbrbrSKIP THE RESORT TRAFFIC. brPositioned exactly on the Killington-Pittsfield border, Powder Run offers the easiest winter logistics in the area. This renovated 2,100 sq. ft. home removes the stress of travel: pull into the large flat parking area (no icy driveway drama), plug into the dedicated Level 2 EV charger, and drop your gear in a mudroom equipped with commercial boot dryers. You are ten minutes from the lifts but lightyears away from the noise of the crowded condo complexes.brbrDESIGNED FOR THE APRES SQUAD. brThe lower patio features a private six-person hot tub that is professionally maintained for your arrival. Upstairs, the open-concept Great Room creates a central gathering point with coffered wood ceilings and a red enamel gas stove. The kitchen is built for real cooking, featuring quartz counters, stainless appliances, and sharp knives. In warmer months, mini-split AC units in every room ensure you sleep cool.brbrFLEXIBLE LAYOUT FOR 8 GUESTS. brWe designed the sleeping arrangements to handle mixed groups easily. Adults can claim the Queen bedroom or the Full bedroom, both laid with clean hardwood floors. The younger crowd has their own space in the bunk room (Twin-over-Full with stairs) or the flex room, which features convertible futons and a TV. Blackout shades and premium mattresses are standard in every room.brbrLOCAL EXPERTS & TICKET DEALS. brWe are a professional local team, living here year-round to support your stay. Booking this property gives you access to our Curated Local Guide, plus preferred access to ski/board rental savings and limited lift ticket deals through our partners.brbrNOTESbr• Shared Access: You share the driveway/parking with our neighbor, Peak Hill Home, but your deck and hot tub are strictly private. br• Large group Ask us about booking both homes to sleep 14.brbrHOUSE RULES & FEES br• Hot Tub: Included free for peak ski weekends (late Dec to mid-March). Optional $95 setup fee for all other dates.br• Quiet Hours: Strictly enforced from 10:00 PM to 8:00 AM. br• Occupancy: Max 8 guests. No parties.br• Smoking/Pets: Strictly no pets. No smoking/vaping inside or within 75ft ($500 fine). br• Exterior Cameras: For safety, cameras are located on the exterior corners of the home. There are no cameras in living areas. br• Safety: No fireworks. Guests must e-sign rental agreement.

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

Pittsfield, Vermont, United States

Bed

Bath

8

Sleeps

$481.22

Silver Spring Chalet — Your Ski-Area Hideaway Near Killington & PicobrBrought to you by GetAwaybrbrWelcome to Silver Spring Chalet, your ideal mountain escape nestled in charming Pittsfield, Vermont. Perfectly situated just 15–20 minutes from the expansive slopes of Killington Resort and Pico Mountain, this inviting home offers comfort, adventure, and relaxation surrounded by Vermont's natural beauty.brbrInside, you'll find a thoughtfully designed retreat spanning two levels with four bedrooms and three full baths, comfortably hosting up to 11 guests. The main level welcomes you with an open living area, vaulted ceilings, a cozy fireplace, and large windows framing sweeping mountain views. A fully equipped kitchen and dining space make mealtime easy and social.brbrDownstairs offers added flexibility with its own kitchenette, family room with game table, and two additional bedrooms — perfect for kids, extended family, or friends. The upper floor features two more bedrooms and a second living area, giving guests plenty of space to relax in style.brbrAfter a day of skiing, snowmobiling on nearby VAST trails, or hiking through lush Green Mountain trails, unwind beneath the stars in your private hot tub on the deck — the perfect spot to soak in crisp Vermont air and mountain views. Whether you're chasing powder, leaf-peeping in the fall, or enjoying quiet evenings by the fire, Silver Spring Chalet is where your Vermont getaway begins.brbrVermont Meals & Rooms Tax Account: MRT-10067229-059

Silver Spring Chalet – Spacious 4BR Retreat in Killington Region, Pittsfield, VT, Sleeps 11

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$687.4

Nestled in the heart of the Green Mountains, this spacious and welcoming home is conveniently located just off Vermont's scenic route 100. Minutes away from Killington Resort's world class skiing, riding, mountain biking, two golf courses (Green Mountain National & Killington) and a stones throw away from the VAST trail system with plenty of parking for trailers. Walking distance to the Clear River Tavern. Enjoy the privacy of this 4-bedroom (each with its own ensuite) 4.5 bath home.brbrThe house has 4 separate bedrooms all on the second floor each with an attached bathroom (shower, sink toilet) and a guest 1/2 bath downstairs. brbrThe large Great Room is perfect for relaxing after a long day of outdoor fun, featuring oversized comfy couches, fur pillows & blankets, a big screen TV, board games & a full sized pool table. brbrEnjoy privacy in the spacious and welcoming backyard, with ample patio furniture set up on the large deck, a propane grill, a sparkling new hot tub, & a custom dug firepit.brbrPlenty of free parking in the private driveway.

Spacious 4BR / 5 Bath Home - Hot Tub / Pool Table / Ample Private Outdoor Space!

Pittsfield, Vermont, United States

4

Bed

4

Bath

10

Sleeps

$147.69

Apartment - Hawk 1-A Mountain Vista RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrEscape to this cozy, one-bedroom, one-bath apartment located on the ground floor with peaceful mountain views, located in Pittsfield, VT. Enjoy your morning coffee on the seasonal patio, complete with outdoor furniture, or unwind inside with the comfort of mini-split A/C, TV, and WiFi.brbrThe well-equipped kitchenette includes a fridge, microwave, dishwasher, coffee maker, toaster, and a spacious island with seating for four—perfect for relaxed meals at home. (Please note: the wood-burning fireplace is not available for guest use.) A portable grill is also provided for easy outdoor cooking.brbrAfter dinner, take a short stroll to the shared private pond and watch the wildlife as the sun sets—an ideal way to end your day. While the pond area is great for relaxing, please remember that swimming, boating, and fishing are not permitted.brbrIdeally located for fun and recreation, you’ll find Thundering Brook Falls, Killington Ski Area, and Silver Lake State Park all within a 20-mile radius. Spend a day hiking amidst gorgeous waterfalls, mountain biking, boating, and fishing in a scenic setting. In the colder months, enjoy easy access to world-class skiing, snowboarding, and other winter recreation. Whether you’re here to explore the mountains or simply savor the quiet surroundings, this inviting retreat offers a comfortable and scenic place to call home.brbrParking notes: There is free parking available for 2 vehicles.brThis rental is located on floor 1.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage 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 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Tranquil apartment w/ mountain views, pond, patio, a/c, kitchenette

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$449.56

8 miles from Killington/Pico mountains, restaurants, nightlife. brbr1000 SqFt 3 Bedroom, 1.5 Bathroom mountain home, recommended for 6 adults, or families with children totaling 8 or less. Floor to ceiling Fieldstone Fireplace with firewood, lots of windows, all wood floors, rustic beams and details. Very neat and clean, with linens provided. Downstairs: Living room opening onto large wraparound deck with BBQ grill and outdoor seating, kitchen seating area for 4 to 6, bedroom with 2 sets of bunks (4 twin beds) with full bathroom (shower/tub), laundry closet (dryer only), ski gear closet/racks. Upstairs half bath with 2 bedrooms (King BR with master balcony, and Full BR). brbrKitchen includes microwave, coffee maker/filters, toaster, mixer, stove/oven, griddle, crock pot, fridge, spices, pots/pans, knives, utensils, dishes, glassware. brStocked with paper towels, dish detergent, plastic wrap/foil, garbage bags, laundry detergent, hand soap, toilet paper. Also lots of board games/DVDs for varied ages, guidebooks, and firewood!brbrNOTE: there is no floor space for air mattresses

Four Season KILLINGTON Getaway!

Pittsfield, Vermont, United States

Bed

1

Bath

8

Sleeps

$551.0

Architect-Designed Chalet in the Green Mountains - A Serene Vermont EscapebrbrbrbrWelcome to your private mountain retreat nestled in the heart of the GreenbrbrMountains. Just minutes from Killington and Pico resorts--and a short scenicbrbrdrive to charming Woodstock--this architect-designed, 4-bedroom, 3-bathroombrbrchalet offers the perfect blend of nature, comfort, and modern design.brbrbrbrThoughtfully built to celebrate the beauty of its wooded surroundings, thisbrbrserene getaway features soaring vaulted ceilings, a striking fieldstonebrbrfireplace, walls of windows, and multiple decks that bring the forest right tobrbryour doorstep. Whether you're sipping coffee among the treetops or unwindingbrbrby the fire, you'll find peace and connection in every corner of this home.brbrbrbrInside, the open-concept layout makes gathering easy and memorable. Thebrbrkitchen is fully updated and ideal for entertaining, while wood floors andbrbrmodern furnishings add warmth and style. Curl up with a book in the cozy loft,brbror relax in the lower level's private sauna after a day of mountain adventure.brbrWith space for up to 10 guests, it's the ideal setting for family retreats orbrbrquiet group escapes.brbrbrbrNote: There are stairways to access the property. Please keep in mind thesebrbrstairways are not accessible with wheelchair.brbrbrbrHighlights include:brbrbrbr * Spacious layout with forest views from nearly every roombrbr * Wood-burning fireplace and firepit (adult use only, seasonal safety rules apply)brbr * Private sauna and cozy loft for reading or remote workbrbr * High-speed Wi-Fi for remote work or streaming (may vary with weather)brbr * Multiple decks for lounging, dining, or stargazingbrbr * Pet-friendly with prior approval and added cleaning feebrbrbrbrCome slow down, breathe deep, and let this tranquil mountainside haven be yourbrbrhome base for Vermont adventure--or simply for rest, reflection, andbrbrreconnection.brbrbrbrPlease Note:brbrbrbrQuiet hours 10 PM–7 AM to preserve the peace of the woodsbrbrbrbrAWD/4WD strongly recommended in winter due to steep gravel drivewaybrbrbrbrFive minutes to a local market; 20 minutes to full grocery storesbrbrbrbrCheck-in is from 4:00 PM; check-out is by 10:00 AM. Early or late check-outbrbrrequests are considered with advance notice.brbrbrbrThere are stairways to access the property. Please keep in mind thesebrbrstairways are not accessible with wheelchair.brbrbrbrMaximum occupancy is 10 registered guests. Events or outside gatherings arebrbrnot permitted.brbrbrbrKindly leave outdoor shoes at the front door and help us preserve the naturalbrbrcharm of the chalet.brbrbrbr

NEW! Serene Architect-Designed Vermont Chalet

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$1866.67

Please don’t waste your valuable time comparing the Swiss Farm Inn to other venues that host group guests (up to 30 people).brNone of them in the Killington area offers an exclusive, spacious living room where all group members can gather and enjoy quality time together quite like we do.brbrAfter sharing meaningful moments in our charming Vermont-style living room and our restaurant-quality commercial kitchen, you can retreat to one of our 14 rooms, each featuring a private bathroom—providing the perfect balance of togetherness and personal space.brbrIn other words, there’s simply no comparison. :)brbr brTake advantage of our commercial kitchen, spacious dining area, large living room with a 70” smart TV, traditional fireplace, and many other amenities.br brWorried about how to feed everyone in your group We’ve got you covered with great meal options:br bra. For those who love to cook, our fully equipped commercial kitchen and spacious dining area are ready for you. It’s a kitchen that can turn even a novice into a Michelin-level chef!br brb. If cooking isn’t your thing, treat yourself to top-shelf, delicious meals from our catering service, lovingly prepared by the town’s best chef. Simply request this service in advance, and we’ll handle the rest to make your stay even more enjoyable.br br brPlease note that Swiss Farm Inn is intended for serene, quality time with family, friends, and loved ones. While we are happy to host large groups, we kindly ask that you treat the inn as you would your own home.br brIf you’re seeking a peaceful retreat, we believe Swiss Farm Inn will be the perfect setting for your stay. Additionally, with advance notice, my husband, a seasoned CPA, CFP, CDFA, PFS, and MBA in Finance, is available to provide complimentary tax and financial consulting. He has been serving clients in public accounting in New York since 2007.br brWe look forward to welcoming you and ensuring your stay is both relaxing and enjoyable. We’re here to assist in any way.br brThank you for choosing Swiss Farm Inn.brbrbrPlease be aware that in Vermont, during the winter season with heavy snowfall, power outages may occur due to snow accumulating on power lines.brbrbrGroup guests during the off-ski season can enjoy kayaking, canoeing, and paddleboarding on Kent Pond.brWe provide 1 canoe, 3 kayaks, and 3 paddleboards with USCG-certified life jackets.brWe can deliver the equipment to the pond on your behalf free of charge.brbr* Please let us know at the time of booking if you plan to use this equipment so we can have everything prepared for your stay at the Swiss Farm

Killington area entire Inn to yourself! 14bd/15bth

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$660.76

Offering free parking pass @ Killington resort! brbrThis magnificent 10-acre estate (~15 mins away from Killington resort) offers breathtaking views of the Killington and Pico ski slopes and the lush mountains, creating an invigorating and awe-inspiring setting. The property features a 12-foot-deep spring-fed pond and a stream that provides abundant fresh water, perfect for taking a dip after a long day.brbr This colossal mountain escape packs a punch with over 4000 square feet of spacebrbrMain floor - Kitchen, dining room, screened in porch, living room and a separate sunroom, master bedroom with bathroom. One half bathroom. brbr1st floor - game room with queen sofa bed. common room, two bedrooms. One bathroom brbr2nd floor - office with one queen sofa bed and one bedroom with a bathroom.

Mountain Top - Fresh Pond - Killington - Hot Tub

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$280.0

This peaceful home is far enough from the commercial Killington Access Road and its crowds, yet not completely isolated. Experience the ultimate mountain vacation -- whether you're in search of vigorous outdoor activities in a beautiful setting, or just a cozy, serene getaway.br2 miles from the Killington town line and 8 minutes from the Access road; 45 minutes from Sugarbush & Okemo; an hour from Mad River Glen. This 5 bedroom/3 bath home has a Gas fireplace in a cozy living room with 50” smart HD television.Minutes away from winter activities such as: downhill skiing / snowboarding cross-country skiing snowshoeing snowmobiling and sleigh riding. Summer activities include hiking, mountain biking, horseback riding, fishing, and much more. Located 2.5 miles from Vermonts #1 public golf course (Green Mountain CC). Kitchen features: dish washer, microwave oven, full size refrigerator, conventional oven with 4 burner range double sink, pots and pans, dishes, glasses and silverware. Washer and dryer 2500 square feet. Has a large deck with hot tub, charcoal grill and gas grill. The house sleeps 14 people: The master bedroom has a queen size bed and a private bath (sleeps 2) with Jacuzzi tub and 50” smart TV. The secondary bedroom has a queen size bed(sleeps 2), third bedroom has 2 twin beds sleeps (2-4 people), bedrooms upstairs include a room with 3 twin beds and lots of floor space and other room has a full size bed (sleeps 2). House includes high speed Wi-Fi. brbrKeywords: House

Killington Vermont Ski and Snowmobiling House

Pittsfield, Vermont, United States

5

Bed

Bath

14

Sleeps

$428.4

Escape to this stunning 4-bedroom, 2-bathroom Cape nestled on 2.4 private acres with panoramic mountain views and the soothing sounds of Townsend Brook as your backdrop. Whether you're here to hit the slopes or simply unwind, this 2005 custom-built home offers the perfect blend of rustic charm and modern luxury. Imagine starting your day with a cup of coffee on the large, covered porch, watching the sun rise over the mountains. Spend your afternoons exploring nearby trails or skiing at world-class Killington, just a quick 15-minute drive away. After a day of adventure, return to your private oasis where relaxation is at your fingertips. The heart of the home is the spacious, open-concept kitchen and dining area, featuring stainless steel appliances, a large island, and a cozy stone fireplace with a convenient gas insert—perfect for creating instant ambiance. The expansive living room, with its comfy seating and a woodstove (non operational), is ideal for gathering with family and friends. Step outside onto the expansive deck, where you'll find a luxurious hot tub and a fire pit waiting to melt your stress away. Breathe in the crisp mountain air as you take in the stunning views—this is where you'll want to spend your evenings, every single night. Upstairs, you'll find four beautifully appointed bedrooms, ensuring everyone has their own space to relax. definitely. With two full bathrooms and sleeping arrangements for eight, this home is perfect for families or groups of friends. Need even more space The walkout lower level features a large laundry room, a versatile bonus room, and plenty of storage for all your gear. Whether you're soaking in the hot tub under the stars, cozying up by the fire, or exploring the natural beauty of Vermont, this home is your ultimate getaway. Don't miss out on this incredible opportunity to experience mountain living at its finest.brbr• The hot tub is included for the peak ski season weekends (December 1st-March 31st). For other periods, there is an optional $195 set up fee. You understand the use of hot tub is at your own risk. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless.br• Our minimum rental age is 25.br• We will provide you with access codes for our smart locks to come and go as you please.br• We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge.br• Our entire home is non-smoking (e-cigs included). There is a $500 charge for smoking.br• For your safety and ours, we have a camera on the front of the house pointed at the driveway. br• Quiet hours are from 10pm - 8am, out of respect of our neighbors and community.br• Fireworks are not permitted.br• This house has a set of steep stairs going up to the front door, however guests may enter on the ground level. br• Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended.brbrSKI RESORTS: Killington Snowshed Base (10.9 miles), Killington K1 Base (11.5 miles), Pico Mountain (9.1 miles)brGOLF: Killington Golf Course (10.9 miles), Green Mountain National Golf Course (5.8 miles)brNIGHTLIFE: Pickle Barrel (8.7 miles), Wobbly Barn (9.2 miles), The Foundry at Summit Pond (8.3 miles)brWEDDINGS: Killington Grand Resort (10.9 miles), Mountain Top Inn & Resort (20.1 miles)brAIRPORT: Rutland Regional Airport (23.9 miles), Burlington International Airport (83.2 miles), Albany International Airport (117 miles), Manchester-Boston Regional Airport (122 miles)

The Getaway: Relax with hot tub, fire pit, and mountain views—just 15 mins from Killington slopes!

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$394.82

Mountain TimebrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWith a warm and welcoming atmosphere and a secluded location close to hiking trails and skiing, this beautiful home is going to make for the ideal space for your next getaway with the people you love. Explore the scenic scenery around you together or pack your clubs and hit the fairway after a short drive to White River Golf Course. Try one of the local restaurants before heading back to your vacation retreat to wind down.brbrInside, the home features three levels of comfort and convenience, the main level boasting an attractive open concept that encompasses the living, dining, and kitchen areas. After a day of hot-weather hiking or some winter action, you can kick back in the living room to catch up with old friends or head into the sitting room to pluck a book off the private library shelves. The kids can spread out some of the provided board games while the wood-burning stove keeps the home nice and toasty. Throw a good record on the turntable then head into the full kitchen to prepare a delicious meal for everyone to savor at the dining table with seating for six. brbrYou can use the private gas grill to host those fun outdoor barbecues on the deck. Don't worry about stains - the private washer and dryer will easily knock out whatever the kids pick up while they eat. Downstairs, you'll find a spacious entertainment area featuring comfortable furniture, a TV, and a work desk for remote workers with and students to handle those last-minute tasks as this property has recently been upgraded with fiber optic internet. When evening falls, gather everyone around the firepit to toast some S'mores and enjoy an evening of stargazing.brbrTHINGS TO KNOWbrStreaming services are available, but guests must log in using their accounts.brThis vacation home is not equipped with air-conditioning.brFour-wheel drive is highly recommended to access the home during winter months.brParties and loud noise are not permitted.brbrParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage 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 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Lovely home close to hiking & skiing w/WiFi, firepit, balcony, wood stove, & W/D

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$542.4

—- The Tweed River House -—br15 minutes to Killington, 11 to Pico. On The Tweed River. Ride & Hike In & Out on the Green Mountain Trails for endless mountain biking, hiking, snowshoeing & X/C skiing. Stunning mountain views. brbrHigh quality furnishings, furniture, textiles, décor and more. Fluffy pillows, dreamy mattresses, Egyptian cotton sheets and soft towels. Fully and tastefully equipped for your visit.brbrHere at the Tweed, come for the true Vermont experience. Pittsfield Village location. You may forget that Killington Resort even exists. Nature is your resort. brbrThe residence was designed for comfort with inviting spaces for cooking, dining, entertaining and privacy with two separate living rooms. brbrUPSTAIRS: Living room with vaulted ceilings and direct mountain views. Oversized windows, and new Vermont sourced oak flooring. We love how the living room flows into the open kitchen and dining room. Perfect for entertaining. With a bespoke butcher block kitchen island and reclaimed wood dining table, the vibe is homey and grounded. Statement wrought iron lighting with Edison bulbs really make the space pop. Convenient powder room off the kitchen with craftsman wainscotting and Danby, VT marble tile. We've got super fast, fiber optic, 500mg internet, reliable wi-fi and a 55-inch smart TV with ROKU streaming your apps. Two more TV's in the Den and BR2.brbrThe upstairs en-suite bedroom is so Zen, that you might not want to get out of bed. Especially with mesmerizing view. Separate dressing room for all your flannel, ripped jeans, and wool socks. Full bathroom with funky globe lights and double sinks. brbrDOWNSTAIRS: Den / Living Room. A sprawling, separate entertainment space with two seating areas, flatscreen TV and two big bedrooms. One with a queen bed, the other with two queen beds and a bunk bed. Full bathroom with jacuzzi tub, infra-red heat lamps and Carrera marble tile. Laundry room with washer / dryer.brbrThree outdoor spaces to enjoy. A 40-foot long deck with direct mountain views, three-season screened porch with dining area and front porch sunset deck. brbrThe Tweed is surrounded by mountains and rivers, nestled in what we think is the most picturesque part of the Green Mountains. Walking distance to the village. Pittsfield is designated as a scenic byway by the state of Vermont. A quintessential village with quaint general stores, farm to table fine dining, and a local watering hole with live music and pool tables. Some say this is Vermont's most authentic ski town. No lifts - tons of character. If you crave secret local spots, ask us .... but don’t tell. :-)brbrWe are looking forward to hosting you here at the Tweed.

15 Minutes to Killington - 2 Living Rooms - Private Mountain Views

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$401.82

Sweet Life — Cozy Mountain Chalet with Hot Tub, Game Room & Pet-Friendly ComfortbrBrought to you by GetAwaybrbrEscape to Sweet Life, a warm and welcoming mountain chalet tucked into the heart of Vermont. Just minutes from Killington Resort, this inviting retreat blends comfort, relaxation, and year-round adventure. Skiing, hiking, vibrant fall foliage, and peaceful woodland scenery are all within easy reach.brThoughtfully designed across three levels, Sweet Life sleeps up to 12 guests and is pet friendly—so the whole family can join the fun. The main living area features vaulted ceilings, a fully equipped kitchen ready for home-cooked meals, and large windows offering partial, seasonal mountain views. After a day on the slopes or trails, gather around the natural stone fireplace and enjoy the firewood provided for your stay.brThe lower level brings the entertainment: a cozy game room with a bumper pool table and flat-screen TV. Nearby, a private indoor hot tub room—wrapped in warm wood paneling and polished tile—offers the ultimate spot to unwind après-ski or after a day of exploring.brStep outside to find a spacious deck and gas grill, perfect for summer barbecues, morning coffee in the crisp mountain air, or stargazing beneath Vermont's night sky.brWhether you're chasing powder at the Beast of the East, exploring foliage routes, or seeking a peaceful retreat in nature, Sweet Life is your comfortable home base for every Vermont adventure. Enjoy mountain charm, cozy touches, and the simple pleasures that make Sweet Life truly special..brbrVermont Meals & Rooms Tax Account: MRT-10067229-020

Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington

Pittsfield, Vermont, United States

Bed

2

Bath

10

Sleeps

$699.47

Hawk 1-A Mountain Vista RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrWelcome to your tranquil mountain retreat in peaceful Pittsfield, VT—a two-story getaway featuring a spacious 4-bedroom, 2-bath main home plus a cozy ground-floor 1-bedroom, 1-bath apartment. With unobstructed views of Killington’s five peaks and a private pond, this property offers everything you need for an unforgettable escape in every season.brbrIn the main house, step inside to discover warm, inviting living spaces filled with expansive windows, plush seating, and rustic, nature-inspired décor. Curl up on the sofa to stream your favorite shows or head upstairs to the fitness area for a quick workout before settling into vacation mode. The well-appointed kitchen is fully equipped with modern appliances, generous storage, and all the essentials for preparing home-cooked meals. In warmer months, take advantage of the outdoor grill and enjoy a summer barbecue on the spacious deck while soaking up the sunshine and breathtaking mountain views. After dinner, wander down to the private pond and watch wildlife gather as the sun sets. Each of the home’s bedrooms welcomes you with soft linens, thoughtful touches, and stunning mountain scenery.brbrThe apartment is perfect for added privacy or extra guests, the separate ground-floor apartment offers peaceful mountain views and a seasonal patio with outdoor furniture—an ideal place to sip your morning coffee. Inside, you'll find mini-split A/C, TV, WiFi, and a well-equipped kitchenette featuring a fridge, microwave, dishwasher, coffee maker, toaster, and a large island with seating for four. A portable grill is provided for easy outdoor cooking. Please note: the wood-burning fireplace is not available for guest use.brbrIdeally located for fun and recreation, you’ll find Thundering Brook Falls, Killington Ski Area, and Silver Lake State Park all within a 20-mile radius. Spend a day hiking amidst gorgeous waterfalls, mountain biking, boating, and fishing in a scenic setting. In the colder months, enjoy easy access to world-class skiing, snowboarding, and other winter recreation.brbrParking notes: There is free parking available for 6 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 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Tranquil house w/ apartment, mountain views, pond, bbq, patio, wifi

Pittsfield, Vermont, United States

Bed

Bath

Sleeps

$373.31

QUIET, WOODED PROPERTY ON KILLINGTON BORDER, minutes from slopes!brbrPeak Hill is a newly rebuilt ski home on the border of Killington and Pittsfield, Vermont and close to all the activity! This home features three bedrooms, two full bathrooms, living room, kitchen, large deck and outdoor area. Spend a day on the slopes (only 10 minutes away) and come back to cook a meal, relax by the gas stove, or catch a show on the smart TV. Sleeping up to 6 people, this is the perfect holiday choice for your family or group. brbrStep into this inviting mountain retreat where the first floor welcomes you with a spacious mudroom, two cozy bedrooms, and a convenient full bathroom complete with a washer and dryer. Ascend the stairs to the heart of the home, featuring a kitchen and living room adorned with a vaulted ceiling, skylights, and abundant windows that flood the space with natural light. The main living area is a cozy haven boasting a gas stove, a smart TV, and plush sofas and lounge chairs for relaxation. Delight in the fully-equipped open kitchen with quartz countertops, sleek dark stainless steel appliances, and a dining area perfect for enjoying meals together. Connected to the living room is a third bedroom and another full bathroom for added convenience. Step outside onto the expansive deck to revel in breathtaking views of the mountain slopes.brbrBedding is as follows:br- Bedroom 1: Queenbr- Bedroom 2: Twin over full bunk bedbr- Bedroom 3: Twin over full bunk bedbr brThe outdoor area and surroundings:brHome offers outside amenities for all seasons and offers a large flat parking space to accommodate everyone.brbrIn SUMMER, FALL and SPRING:br- Enjoy the outdoor fire pit and seating area - roast your marshmallows by the fire.br- Sip your beverage and play outdoor games in a quiet wooded setting br- Soak in the fall foliage and peaceful surroundings br- Take advantage of two free golf, mountain bike, gondola and adventure center passes (upon request, limited availability)br- Enjoy the large spacious deckbrbrIn WINTER:br- Store your ski and snowboard in the dedicated storage shed by the front doorbr- Park in the flat parking area right off major Vermont roadbr- Hang your gear in the foyer/mudroom and dry your boots with the provided boot dryerbr- Warm up by the gas stovebr- Take advantage of discounted 50% off lift tickets (upon request, limited availability) brbrOTHER THINGS TO NOTEbr• Hot Tub: The hot tub is included for the peak ski season weekends (late-December to mid-March). For other periods, there is an optional $95 set up fee. You understand use of hot tub is at your own risk and that special risks may be involved in using the hot tub. You accept full responsibility for any bodily injury arising from use of the hot tub, and hold owner and property manager harmless.br• Peak Hill shares a driveway and parking area with another property - Powder Run. Each house has a dedicated parking for 2+ cars with overflow parking located at the base of the property.br• For your safety and ours, we have a camera on each corner of the house. They are not in any of the living areas.br• The Killington, Vermont area is the perfect place to get away from it all no matter what season it is. There are tons of outdoor activities including: skiing, snowboarding, hiking, antiquing, golf, swimming, shopping, sightseeing, mountain biking and many more.br• We're located less than 4 miles to the Killington Access Road and 8 miles to the slopes. Two golf courses are within 10 minutes of the house with Green Mountain National only 5 mins away. The town recreation center is just a short distance away and features a swimming pool, soccer field, tennis courts, baseball diamond and playground. You'll also find plenty of trails, ponds, lakes, swimming holes and quaint Vermont towns a short drive away.br• Please be sure that you have entered the correct number of guests as we may have a per-person per-night surcharge to cover expenses. You can contact us for a custom quote before booking.br• Our minimum rental age is 25.br• We will provide you with door codes for our smart locks for contactless check in and out.br• We have some flexibility around our standard check in and check out times depending on other bookings. Guaranteed early check in or late check out may be available for an additional charge.br• Our entire home is non-smoking (e-cigs included). You may only smoke 75 feet away from the property. There is a $500 fine for smoking in or near the house.br• You must e-sign and return our written rental agreement after you complete your booking.br• The property is NOISE SENSITIVE. Strict quiet hours must be observed from 10pm - 8am. We use Minut, smart home technology that measures volume levels throughout the property and allows us to respond to noise nuisances without disrupting your stay. Minut is 100% privacy compliant and is required on this property. If you have any questions, please ask. We are committed to your comfort so please let us know if we can do anything during your stay to make it more enjoyable.br• Fireworks are not permitted.br• Pets are not permitted. There is a $750 fine for any unauthorized pets.br• Please be advised that this property utilizes a ladder to access the bunk beds. By renting this property, you are agreeing to hold the owner and property manager harmless for any injury or death that is resulting from the use of the ladder.br• Winter weather is unpredictable. We do not offer weather-related refunds and recommend purchasing travel insurance for any unforeseen events. All wheel drive and winter tires are also recommended.brbrSKI RESORTS: Killington Snowshed Base (7.9 miles), Killington K1 Base (8.6 miles), Pico Mountain (6.2 miles)brGOLF: Green Mountain National Golf Course (2.9 miles), Killington Golf Course (7.9 miles)brDINING / NIGHTLIFE: Pickle Barrel (5.8 miles), Wobbly Barn (6.3 miles), The Foundry at Summit Pond (5.4 miles), Rivershed (4.8 miles)brWEDDINGS: Killington Grand Resort (8.0 miles), Mountain Top Inn Resort (14.1 miles)brAIRPORT: Rutland Regional Airport (21.2 miles), Burlington International Airport (71.6 miles), Albany International Airport (113 miles), Manchester-Boston Regional Airport (116 miles)brbrWe look forward to hosting you!

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Pittsfield, Vermont, United States

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$1666.0

Rent an entire Inn to yourself (really, the whole place is yours)! brbrEarly check in times and late check outs! Check in as early as 10am, check out by 4pm! brbrPrivate bathroom with shower for each of the 9 guest rooms, The Northeast House is located a quick 15 minute from the lifts at Killington. We welcome you to cook in the commercial kitchen, seat everyone together in the dining room, enjoy a drink at the bar, & relax in the living room where we have satellite TV service. Your stay at The Northeast House is sure to be relaxing, comfortable, convenient, and fun!brbrThere is high-speed fiber optic internet at the house with enough power to connect everyone's device!brbrEric resides in the apartment connected to the rear of the house, it does not share any common walls with the main house and has it's own entrance and driveway. Eric is available for any needs that arise during your stay.brbrAny questions Feel free to ask! brbrOccasionally we can accommodate two night stays, please message to discuss

Private Killington Area Inn all to Yourself!

Pittsfield, Vermont, United States

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$436.52

Main - Hawk 1-A Mountain Vista RetreatbrbrOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'brbrThis tranquil, two-story home, surrounded by lush green areas and nestled into the peaceful Pittsfield landscape, boasts unobstructed views of Killington's five peaks and everything you need for an unforgettable escape. brbrIdeally located for fun and recreation, you’ll find Thundering Brook Falls, Killington Ski Area, and Silver Lake State Park all within a 20-mile radius. Spend a day hiking amidst gorgeous waterfalls, mountain biking, boating, and fishing in a scenic setting. In the colder months, enjoy easy access to world-class skiing, snowboarding, and other winter recreation.brbrInside this gorgeous hideaway, you’ll discover ample living areas bursting with expansive window views, plush seating, and charming rustic decor that seamlessly blends the natural elements. Feel right at home snuggled up on the sofa while streaming your favorite movies. Perhaps sneak in a quick workout in the upstairs fitness area! A well-appointed kitchen boasts modern appliances, plenty of storage space, and everything you need to create delicious home-cooked meals. Even better, utilize the outdoor grill for a summer barbecue while everyone lounges on the spacious deck, basking in the sun and breathtaking scenery. After dinner, walk down to the private pond on the property and observe the wildlife as the sun sets. Each bedroom welcomes you with soft, cozy linens, thoughtful accents, and even more mountain views. brbrThings to KnowbrCheck-in time: 4:00 p.m.brCheck-out time: 10:00 a.m.brAll guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 p.m. to 8:00 a.m.brNo smoking is permitted anywhere on the premises.brbrParking notes: There is free parking available for 4 vehicles.brbrPlease note: this home resides in a noise-sensitive area and the owners participate in our Good Neighbor protection program. Our smart home technology will alert our team if excessive decibel or occupancy levels are detected, allowing us to reach out directly with a reminder of maximum occupancy and quiet hours. This technology is privacy compliant, and only monitors the presence of decibels and devices-not any personal conversation or information. Thank you for supporting our efforts to be good neighbors!brbrDamage 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 21 years of age to book. Guests under 21 must be accompanied by a parent or legal guardian for the duration of the reservation.

Tranquil retreat with generous deck, fitness area, & amazing views

Pittsfield, Vermont, United States

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$372.11