Vacation rentals in Pittsfield

Guest suite in Stockbridge

5.0 out of 5 average rating, 116 reviews

Studio Suite with Vermont Style & Amazing Views

Central to Killington, Pico & Sugarbush Ski Areas. Breathtaking views. Features all Vermont has to offer in any season - Golf, Downhill & X-country Skiing, nearby VAST trails, Snowshoeing, Hiking, Trail & Road Biking. Unit is en suite w/sitting area, dining table/desk, kitchenette (no stove). Shower and toilet with ADA bars. Handicap accessible. Large closet, dresser. Streaming TV/DVD/VHS, selection of games, discs and tapes. 2 entrances - public and private. Stone patio and fire pit. Quiet.

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5.0 out of 5 average rating, 56 reviews

Hot tub|Sauna|Movie Room! 8 min to Killington Mtn!

Welcome to your perfect Killington retreat! Our home offers the ideal getaway for relaxation & adventure. Unwind in the HOT TUB, rejuvenate in our outdoor SAUNA, or simply take in the stunning VIEWS that surround you. Located 7 miles, <10 minutes from Snow Shed & the slopes of Killington & <9 min to Pico Mtn, as well as an array of downtown restaurants, our home is the perfect base for your VT adventures. Once you experience the warmth & comfort we provide, you'll want to return again & again!

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A spa-like bathroom features a luxurious soaking tub beside a modern shower enclosed by glass. Multiple windows offer views of the wooded surroundings, while elegant wood accents complement the radiant floor heating. A stylish sink and cabinetry enhance the tranquility of the space.

4.93 out of 5 average rating, 54 reviews

Romantic Retreat, Hot Tub, near Killington Mtn

This architect-designed, contemporary mountain chalet features all the classic elements – including stone fireplace with wood stove, soaring vaulted wood ceilings, walls of glass and wide pine floors. This stunning home has a lovely wooded backdrop adjacent to Hawk Mountain pond. It is located in Pittsfield, 8 miles from Killington. Kitchen has high-end appliances, quartz countertops and custom backsplash. Stunning spa-like oasis bathroom. Several decks, fire pits, next to pond.

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4.98 out of 5 average rating, 195 reviews

Cabin in Pittsfield

Tiny Vermont Cabin!

Newly built tiny cabin in the woods of Vermont! Perfect for a quiet get away and close by outdoor fun! Killington and Pico Mountain is 15 minutes away! Sugarbush is 50 minute drive. Coming to Pittsfield for a wedding? Riverside Farm is only .7 of a mile down the road! Winter: MUST have AWD/4x4 for winter access on dirt road and driveway. Snow tires recommend. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the beauty Vermont has to offer!

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4.95 out of 5 average rating, 64 reviews

Trailside Retreat: Hike & Bike From Your Doorstep

Airbnb Top 10% Guest Favorite - Ride & Hike the Green Mountain Trails from your door. Location: 5 mins to Green Mountain National Golf, 15 mins to Killington Resort. 1 minn to Village Green Stores. The Space: Modern retreat with stunning mountain views. Two separate living rooms offer privacy for families. Amenities: River swimming access, hiking and mountain biking from your door. Fast Fiber-optic Wi-Fi, secluded, quiet setting. Reliable, 5-star hospitality in the heart of Vermont

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4.98 out of 5 average rating, 123 reviews

An exterior view of the home showcases a patio adorned with string lights, providing a warm glow against the backdrop of rolling green hills. The hot tub is visible nearby, adding to the inviting outdoor space perfect for gatherings.

Cabin in Killington

Camp Poe: HotTub/AC/Game Room/6acres/Patio/EVchrgr

Experience the heart of the Green Mountains on our private 6 acre estate. Camp Poe at Estabrook is the ultimate Vermont getaway--wide plank floors, fully stocked farmhouse kitchen, wooden beams and a two story family room w/ a wood burning stove. This 3200 sq ft house is perfect for entertaining with two separate living rooms, bar, game room, 10ft dining tables (inside AND outside) and hot tub. 13 min to Killington Mtn & 4min to the #1 golf course in VT! EV Charger available for guest use.

LocationFamilySkiing

5.0 out of 5 average rating, 19 reviews

NEW 3BR Home: Hot Tub, AC, EV & Lift Ticket Deals

BRAND NEW HOME. You want the mountain access without the condo noise. Powder Run is your answer. It is a brand new 2,100 sq. ft. sanctuary on the Pittsfield border of Killington with exclusive ski rental and limited lift ticket deals. Park in the flat driveway, plug in your EV, and dry your boots in the mudroom. Whether you are soaking in the private hot tub or gathering by the red enamel gas stove, this is where the adventure slows down. Sleeps 8 with AC and generator.

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4.97 out of 5 average rating, 165 reviews

A stone pathway is framed by lush greenery and garden beds leading to the entrance of the chalet. Soft lighting from lanterns illuminates the steps, creating a welcoming atmosphere as it transitions from the natural surroundings to the home's entrance.

Chalet in Stockbridge

Gnome Home Mountain Ski Chalet w/Sauna Killington

Mountaintop Chalet perched in the heart of Green Mountains. Enjoy true mountain living all year long 25m to Killington, White River access minutes from home, abundance of hiking trails, and golf courses. Central to Killington, Rochester, & Woodstock. After your adventures, return to a welcoming & comfortable home with beautiful views from every room, multiple decks, new! fireplace, & sauna, and plenty of special touches to help you unwind and relax.

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A spacious living area features a large leather sectional sofa facing a glass coffee table. Natural light floods in through multiple large windows, framed by dark trim. A cozy reading nook is seen in the corner, adorned with a decorative throw and a small side table.

4.98 out of 5 average rating, 44 reviews

Skyeburst | Modern Mtn Home

| Welcome to The Skyeburst House | Reimagined 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.

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Vacation home in Pittsfield

The exterior of a spacious home is viewed from the backyard, featuring a wooden facade and large circular window. A well-maintained lawn surrounds a deck with outdoor seating, an umbrella, and a hot tub, framed by lush greenery and trees.

4.91 out of 5 average rating, 64 reviews

The Barn Door Lodge

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 and Pico 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. Enjoy the privacy of this 4-bedroom (each with its own ensuite) 4.5 bath home.

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4.81 out of 5 average rating, 16 reviews

Mountain Home with Scenic Views

A unique post and beam log cabin with beautiful scenic mountain views. 15 minutes from Killington and Pico ski areas. This one of a kind house offers an open floor plan with a great room and fireplace. Master suite has its own fireplace, jacuzzi tub and balcony. A loft area with pool table and tv . Outside hot tub with mountain views. Two car garage to park in on cold snowy nights. Large basement off garage makes getting out of your ski gear easy.

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A welcoming living area features a large fieldstone fireplace, with a soft couch and several armchairs arranged for comfort. A coffee table sits in the center of the space. Above, warm lighting illuminates an adjacent dining area, enhancing the cozy atmosphere.

4.85 out of 5 average rating, 256 reviews

Killington area home - 4 seasons - hot tub and A/C

Set on a private road in the hills of Pittsfield, our house welcomes you year-round. Right in the heart of the Northeast’s best winter-sports, it's convenient to Killington ski resort, VAST snowmobile trails, Mountain Meadows cross country skiing and Green Mountain National Golf course. Furthermore, there are wonderful hikes and mountain biking to be done on the property and beyond - particularly beautiful in the fall.

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Popular amenities for Pittsfield vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Pittsfield

4.95 out of 5 average rating, 38 reviews

Post & Beam Home Ideal for Families or Groups

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4.95 out of 5 average rating, 77 reviews

Killington Chalet: Hot Tub, Fireplace, spacious 4b

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A spacious deck offers a serene view of rolling hills and trees. Two chairs and a coffee table are positioned, with two cups placed on the table. The structure extends with wooden railings, creating an inviting space for relaxation amidst nature.

4.86 out of 5 average rating, 96 reviews

Beautiful ski house 8 min from mountains

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5.0 out of 5 average rating, 16 reviews

Cedar Wood Lodge

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5.0 out of 5 average rating, 88 reviews

The exterior of the A-frame cabin is showcased against a twilight sky, featuring distinctive triangular architecture and warm, inviting lights. Large windows are framed by dark cladding, while the entrance is highlighted by a set of steps leading to a welcoming front door.

Cabin in Killington

Green Mountain Yay Frame

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A spacious yellow house is set against a backdrop of trees, with snow covering the ground. Sunlight casts soft shadows on the surface. The architecture features multiple gabled roofs and large windows, creating a bright, inviting appearance that complements the winter landscape.

5.0 out of 5 average rating, 21 reviews

Entire home- Killington, Vermont Ski, Hike, Bike

LocationFamilyQuiet

Superhost

Home in Stockbridge

4.92 out of 5 average rating, 13 reviews

Ski/MTB/Arcade/Pool Table near Killington/Pico/Sug

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A spacious game area features a shuffleboard table at center, illuminated by overhead lighting. Large windows provide natural light and views of the outdoors. Comfortable seating is available at a circular table nearby, complemented by a decorative area rug on the wooden floor.