Vacation rentals in Stockbridge

4.99 out of 5 average rating, 223 reviews

A rustic sugarhouse cabin is surrounded by lush greenery, with trees lining the background. The building features a metal roof and several windows that reflect natural light. A picnic table is placed on the covered porch, offering a comfortable space for relaxation.

Cabin in Royalton

Genuine Vermont Sugar House on 70 peaceful acres.

Stay in this genuine Vermont sugarhouse. Our family took great pride in making Maple Syrup and now we take that same pride in sharing this private piece of Vermont with you, our guests. There are trails that will take you through our 70-acre property including the sugar bush we used for the sugarhouse. Relax in the quiet beauty of rural Vermont. Located near the geographical center of VT. We do welcome friendly housebroken dogs. Please see other details under show more. Part of Three Maples LLC.

Guest suite in Stockbridge

A charming red barn-style building is shown, featuring a metal roof and large display windows. A sign indicating 'Gallery & Gifts' is visible, alongside a stone pathway. The surrounding green grass and mountains in the background add to the rural setting.

5 out of 5 average rating, 100 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.

The exterior of the upper unit duplex is surrounded by snow, showcasing a wooden deck with a railing and steps leading to the entrance. A prominent stone chimney rises from the roof, and large windows provide a view of the surrounding forest.

4.92 out of 5 average rating, 183 reviews

Killington ski house winter MTbike -new jacuzzi

Killington Ski Area with access to snowmobile mountain biking trails. This 3 bedroom, 2 bath upper unit duplex. with outdoor private Jacuzzi open year round with barbecue on very nice decks for those nicer days , snow mobile right from the house , on the tweed valley vast trails , in the summer mountain bike on the green mountain trail system right on our mountain keep us in mind for the summer event like the spartan race and the peak series Mt biking events Fantastic unit check our reviews

4.93 out of 5 average rating, 123 reviews

The treehouse design features large windows and wooden siding, surrounded by lush greenery. An expansive deck is equipped with comfortable seating and a fire table, providing a serene outdoor space for relaxation.

Treehouse in Stockbridge

Romantic Treehouse- Hot tub, A/C, 20 Min to KLT

New treehouse was built by me with my own two hands during the pandemic. The architect styled design is one of a kind with huge windows. Radiant Heat, custom bathroom/kitchen. My grandparents once owned and operated a dairy farm in the area and I want to share this treehouse and surrounding area with my guests. Ski or Ride in only 20 min to Killington and resorts. My treehouse is located on the historic ski highway with Killington-20 min, Pico, Okemo, Sugarbush, Saskadena Six, and Stowe.

Superhost

An A-frame chalet features a sloped metal roof and wooden exterior, surrounded by verdant greenery. A welcoming wooden deck with stairs leads to the entrance, inviting guests to enjoy the natural setting. Large windows allow for sunlight to illuminate the space.

4.84 out of 5 average rating, 164 reviews

Vermont Chalet

Killington Skiing, Pico Peak, Sugar Bush, Mad River are all within distance. Killington is 14 miles away. Fall folliage is fabulous; kitchen well equipped; very light and lovingly cared for. Spring and summer are just as wonderful. I am walking distance to the White River where there is canoeing, tubing and swimming. Within walking distance is the Gaysville Campgrounds. Here you'll find river access to a fabulous swimming hole in the White River as well as trails to explore or walk your dog.

Superhost

A charming farmhouse exterior is shown at night, with warm light glowing from multiple windows. The snowy landscape surrounding the house is accentuated by tall trees under a dark blue sky. The roof displays a gentle slope covered in a blanket of snow.

Home in Stockbridge

4.87 out of 5 average rating, 146 reviews

Escape to Vermont

Welcome to the Red House at Stony Brook! This remodeled 1800's farmhouse offers peace, solitude and comfort in Vermont's national forest. Gaze at stars from the bedroom window and decompress in the mountains. Or, set out for a day of cycling, hiking, skiing and exploring all Vermont has to offer. A chance to experience wildlife, such as moose, birds, bears, turkeys and more. Nearby are Killington Mtn, Sugarbush, famous cycling roads, and several of VTs world renowned eateries and breweries.

4.95 out of 5 average rating, 112 reviews

A spacious outdoor deck features a mix of seating, including lounge chairs and a table set for two. String lights are elegantly draped above, providing a warm glow. Surrounding trees add to the natural setting, enhancing the peaceful atmosphere.

Cabin in Stockbridge

1958 Classic "Hunting Cabin" w/ Breathtaking Views

Welcome to CAMP TREETOPS, located in the heart of the beautiful Vermont mountains. Our cabin is nestled at the top of a private mountain, surrounded by breathtaking views of Killington, Pico mountains, and the White River. Originally purchased from a Sears & Roebuck catalog as a hunting cabin owned by the same family until 2019. The cabin has since been transformed into its original vintage classic camp décor with antique furnishings and unique vintage finds that take you back in time.

4.98 out of 5 average rating, 160 reviews

A newly built tiny cabin is nestled among lush green trees, accessed by a wooden deck leading to a cozy seating area. Natural stones and grass surround the cabin, enhancing its peaceful woodland setting, while warm lights add a welcoming touch.

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! MUST have AWD/4x4 for winter access on dirt road and driveway. Cozy up by the newly added propane fireplace with an easy click of a button! Come experience the winter beauty Vermont has to offer!

4.99 out of 5 average rating, 247 reviews

A modern wooden house is surrounded by lush greenery, featuring a small pool on a wooden deck. Views of distant mountains and a serene lake are visible in the background, creating a tranquil outdoor setting.

Tiny home in Warren

Luxury Glass Tiny House - Mountain View + Hot Tub

Immerse yourself in nature at Vermont's most unique Airbnb, located in the heart of the Green Mountains. This upscale mirrored glass house was built in Estonia and combines Scandinavian design with jaw-dropping Vermont views for an unforgettable experience. You'll return home feeling rejuvenated after relaxing in a hot tub overlooking Sugarbush Mountain or waking up with a panorama of Blueberry Lake at your feet. *One of Airbnb’s Most Wish-listed Stays of 2023*

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.

4.96 out of 5 average rating, 132 reviews

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.

4.95 out of 5 average rating, 481 reviews

A spacious living area features a light grey sectional sofa with cozy throw pillows. Natural light floods in through large glass doors that open to the yard, while a modern ceiling fan hangs above. A rug defines the seating arrangement, and simple decor adds warmth.

Cabin in Rochester

Black haus: a hip, cool house hidden in a forest.

You’ll love our place because of the high ceilings, the rural location, the coziness and its sense of place in nature. Our place is great for couples and solo adventurers who enjoy their privacy, who want to get away from it all but be close enough to a more 'country-urban' vibe. There is a deck for sunning, quite a large front and back yard. A great kitchen for meals at home, a forest to explore and miles of trails to mountain bike or hike.

4.98 out of 5 average rating, 113 reviews

The treehouse is perched among lush green foliage, showcasing a rustic wooden exterior with an A-frame design. A spacious deck features seating areas, inviting relaxation while surrounded by towering trees. The natural setting enhances the sense of seclusion and connection to the forest.

Treehouse in Bethel

Crooked Maple Treehouse

Nestled in the heart of the Vermont Green Mountains, the Crooked Maple Treehouse is handcrafted from timber harvested and milled on-site by the owner, Brett. Thoughtfully crafted to create a rustic and cozy retreat. Take this opportunity to escape your busy everyday life to appreciate the simplicity and solitude of living off the grid at the Crooked Maple.

Vacation rentals for every style

Get the amount of space that is right for you

Houses

A space thats all yours, with room for everyone

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Stockbridge vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Stockbridge

5 out of 5 average rating, 29 reviews

A spacious dining area features a large wooden table surrounded by black chairs, with natural light flowing through expansive glass doors. The high ceiling accentuates the open floor plan, and a glimpse of an outdoor seating area is visible through the doors.

Home in Pittsfield

Skyeburst | Modern Mtn Home

5 out of 5 average rating, 15 reviews

An overhead view of the open-concept living area is captured, showcasing vaulted ceilings and a combination of modern and retro furnishings. A large sectional couch with orange throw pillows complements a coffee table, while the fully equipped kitchen is adjacent, featuring sleek appliances and a decorative rug.

Home in Pittsfield

Chalet Suite | 2BR+Loft (Secure Mtn Bike Storage)

Superhost

A small wooden cabin is positioned amidst snow-covered ground, with a clear blue sky overhead. Large windows allow natural light to enter, while bare trees surround the structure, creating a serene winter landscape.

Cabin in Stockbridge

4.91 out of 5 average rating, 47 reviews

Stunning Artist Retreat Cabin

4.93 out of 5 average rating, 28 reviews

An inviting cabin is illuminated by warm string lights, highlighting its rustic wooden exterior. The porch is furnished with a small table and chairs, while a golden retriever sits calmly on the deck. Lush greenery surrounds the cabin, enhancing the tranquil setting.

Cabin in Rochester

The Creek Cabin at Sky Hollow

4.95 out of 5 average rating, 83 reviews

A cozy cabin with a crisp wooden exterior is located amidst lush greenery and trees. A serene pond is visible nearby, with a flower farm and several outbuildings in the background. Expansive fields lead towards the picturesque landscape of mountains under a cloudy sky.

Cabin in Bethel

The Gourmet Cabin at Stitchdown Farm

4.98 out of 5 average rating, 60 reviews

The exterior of a two-story house is depicted, featuring dark green siding and a welcoming entryway under a wooden porch. A manicured lawn surrounds the property, with a gravel path leading to the entrance. Trees and distant vehicles are visible in the background.

Cottage in Barnard

31 Lili West - across from Silver Lake on 5 acres

4.89 out of 5 average rating, 66 reviews

A spacious living room features large windows that provide views of the surrounding trees. A comfortable sectional sofa is adorned with colorful cushions, while a decorative coffee table sits on a patterned rug, complementing the wooden beams above.

Home in Pittsfield

Hideaway Mountain at Killington

The chalet is surrounded by a vibrant autumn landscape, with trees displaying a range of warm colors. The wooden structure is elevated, providing a view of the natural beauty, while the nearby area showcases the changing foliage of the season.