Holiday houses in Pittsfield

Guest suite in Stockbridge

5.0 out of 5 average rating, 117 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.

ValueFamilySleep quality

A cozy outdoor fire pit is surrounded by natural stone, with a warm fire dancing in the center. The modern home is visible in the background, illuminated by string lights. The structure features a deck and tall windows, set against a wooded landscape at dusk.

4.98 out of 5 average rating, 55 reviews

Hot Tub|Sauna|Relax! 5 mins to downtown Killington

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!

LocationFamilyDecor

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, 56 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.

LocationFamilyNearby

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!

LocationValueBackyard

4.95 out of 5 average rating, 65 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

LocationFamilyDecor

4.97 out of 5 average rating, 154 reviews

A bright living area features large windows that frame views of the surrounding forest. Natural light enhances the wood-paneled walls. A comfortable sofa and chair are positioned around a central coffee table. A small, modern wood stove provides warmth, creating a cozy atmosphere.

Cabin in Goshen

The Berghüttli: Glowing Swiss Hut in the Forest

The Berghüttli ("little mountain hut") is a Swiss-inspired hut and farm stay surrounded by National Forest in Goshen, VT (pop. 168). A completely private escape—no other structures in sight, just woods and quiet. Inside, a wall of windows brings the forest right up to you, while glowing maple plywood fills the space with warm light. High-speed fiber internet runs a reliable 300 Mbps. Stay connected or switch off completely. Search "The Berghüttli" on YouTube for a video tour.

FamilyValueWi-Fi

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.

FamilyLocationTV

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, 45 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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Holiday 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.

LocationFamilyBathroom

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.

LocationFamilyView

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.

LocationFamilyAccuracy

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.

4.89 out of 5 average rating, 100 reviews

Game Room + Hot Tub - 7BR updated home

🎿 10 min to Killington Resort 🔥 2 beautiful living rooms – games & entertainment 🛁 5-Person hot tub - open year round! 🍷 Updated kitchen w/ Viking & Frigidaire appliances 🛏️ All bedrooms upstairs for added privacy 🌳 Peaceful setting on a private road 🔥 Seasonal outdoor fire pit & dining area 🅿️ Free on-site parking Perfect for ski trips, family gatherings, golf weekends, and year-round mountain escapes!

LocationValueCleanliness

Popular amenities for Pittsfield holiday rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Pittsfield

4.95 out of 5 average rating, 80 reviews

Killington Chalet: Hot Tub, Fireplace, spacious 4b

ValueLocationIndoor spaces

4.98 out of 5 average rating, 41 reviews

Holiday Haus- AC, game room, near golf

LocationFamilyLaundry

5.0 out of 5 average rating, 16 reviews

Cedar Wood Lodge

LocationFamilyCleanliness

Superhost

Home in Stockbridge

4.92 out of 5 average rating, 13 reviews

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

FamilyLocationKitchen

A kitchen features warm wood tones with modern stainless steel appliances, including a refrigerator and microwave. A central island with seating complements a dining area, where a rustic wooden table chairs invites gathering. Large windows provide views of the surrounding nature.

4.86 out of 5 average rating, 99 reviews

Killington family friendly all season house

ValueLocationCleanliness

5.0 out of 5 average rating, 23 reviews

Rockwell Haus: modern cabin 14 min from Killington

LocationFamilyLaundry

Superhost

Home in Stockbridge

5.0 out of 5 average rating, 4 reviews

Bear Foot Lodge | 4BR/4BA by Killington Ski Resort

LocationFamilySleep quality

Superhost

A secluded cabin is surrounded by a snowy landscape, with tall evergreen trees visible in the background. The sun is seen shining brightly above the cabin, and a thick blanket of snow covers the ground, creating a serene winter scene.