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.

FamilyLocationSkiing

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.

LocationFamilyCondition

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!

LocationValueBathroom

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

LocationFamilyHospitality

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.

FamilyLocationTV

An aerial view showcases the expansive 10-acre estate surrounded by snow-covered mountains. The property features a serene, spring-fed pond reflecting the landscape, with a spacious home nestled near the water, offering an inviting retreat in a tranquil setting.

4.95 out of 5 average rating, 40 reviews

Mountain Top - Fresh Pond - Killington - Hot Tub

This magnificent 10-acre estate - ~15 minutes away from Killington and Pico resort - offers breathtaking views of the Killington and Pico ski slopes and the lush Green Mountains, creating an invigorating and awe-inspiring setting. The property's oasis-like atmosphere features a 12-foot-deep spring-fed pond and a stream that provides abundant fresh water, perfect for taking a dip and enjoying the outdoor shower. Please note that the indoor fireplace has been disabled for safety reasons

FamilyValueAccess

4.97 out of 5 average rating, 110 reviews

Chalet in Killington

The Overlook - Views | Hot Tub | Fire Pits | Games

Escape to stunning mountain views at The Overlook. Just 5 min from Killington Resort, restaurants, and shops. Enjoy the peacefulness of this private cozy mountain chalet after a long day of adventure and unwind in the hot tub, game room, or by the fireplace. Convenient Level 2 EV charger compatible with all EVs at the chalet. 🏔️ Mountain View 🌄 Large decks and balcony 🏖️ Hot tub ⚽️ Game room 🍗 Propane grill 🍳 Fully stocked kitchen 🪵 Fire pit 🔥 Fire table ⚡️Level 2 EV Charger

FamilyLocationAmenities

4.97 out of 5 average rating, 155 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.

FamilyValueAmenities

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.

ValueFamilyRiver

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.

FamilyLocationHospitality

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.

FamilyLocationComfort

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.

LocationValueBiking

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

FamilyValueAmenities

Holiday home in Pittsfield

The spacious Great Room features a vibrant red pool table at its center, surrounded by comfortable seating areas. A large flat-screen TV is positioned near large windows, allowing natural light to illuminate the wooden ceiling and floors.

4.91 out of 5 average rating, 64 reviews

The Barn Door Lodge

LocationValueNearby

4.95 out of 5 average rating, 38 reviews

Post & Beam Home Ideal for Families or Groups

FamilyValueSkiing

A modern cabin stands surrounded by lush greenery, featuring a dark exterior that contrasts with the natural landscape. A spacious deck is supported by wooden beams, and large windows invite natural light. A stone wall borders the property, adding character to the setting.

4.96 out of 5 average rating, 45 reviews

Skye Ridge Lodge: Private Hot Tub, Open Concept

FamilyLocationBathroom

5.0 out of 5 average rating, 16 reviews

Cedar Wood Lodge

FamilyLocationSkiing

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

LocationFamilyNearby

5.0 out of 5 average rating, 22 reviews

Home in Stockbridge

Ski Home/Arcade Mountain Views Near Killington/Woo

LocationFamilySleep quality