Vacation rentals in Berkshire

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Top-rated vacation rentals in Berkshire

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

A modern living area features a comfortable brown sofa beside a wooden coffee table. Exposed wooden beams run across the ceiling, while a staircase leads to an upper level. Natural light fills the space through large windows, creating a warm and inviting environment.

Cabin in Montgomery

4.94 out of 5 average rating, 190 reviews

Jay Peak Retreat

Jay Peak Retreat, Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This cabin offers an open-concept layout perfect for cozy gatherings and après-ski. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, fire pit, outdoor furniture. 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!! Four ski resorts nearby of the cabin Jay, Smuggs, Stowe, Mont Sutton!

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Guest favorite

A spacious outdoor area is visible, featuring a large tree providing shade. A gravel driveway leads to a charming cottage with a glass-covered porch. Nearby, a separate structure is partially visible, and several chairs are arranged for seating, inviting relaxation in the serene surroundings.

Cottage in Dunham

4.93 out of 5 average rating, 254 reviews

Quiet stay on 76 acres land with pool!

Please read complete description before you book. A short 1 hr. car ride from Mtl will bring you to the picturesque Eastern Townships. This beautiful little century home is located on 76 acres with a forest and meandering streams. The in-ground swimming pool is open from June till September (it's not heated). The house is bright, clean and has a comfy feel to it. It’s fully equipped kitchen, veranda, BBQ, and the campfire is quite the treat. Trails from the backyard will take you into the woods.

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Guest favorite

A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.

Treehouse in Newport

4.97 out of 5 average rating, 339 reviews

Secluded Luxury Treehouse - Hot Tub + Projector

Our treehouse is a haven of well-being, peace, and elegance. In our stunning modern treehouse we have brought relaxation to a whole new level. Surrounded amongst us is nothing but woods & wildlife. An experience not to be missed. Put your favorite movie on the projector, get Zen in the cozy sun room, jam out to music on the record player, or grab a towel, and head for the custom cedar hot tub. It is time to create core memories that will never be forgotten. Welcome to a little slice of heaven.

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Top guest favorite

A spacious cabin is set in a lush green landscape, surrounded by tall trees. Large windows dominate the front, allowing natural light to fill the interior. The sloped grassy yard leads to a relaxing outdoor space, perfect for enjoying the serene woodland views.

Cabin in Enosburg

5.0 out of 5 average rating, 209 reviews

The Rustic Retreat at Twin Ponds

Take it easy and make yourself right at home in our woodsy cabin tucked away in the Cold Hollow Mountains. As you head down the drive, let your worries fade away. You’re now on cabin time. Relax in the clawfoot tub after a day of travel or prepare a home-cooked meal in the well equipped kitchen. Wake up to coffee on the deck or take a stroll around the pond. And you won’t regret kicking back in the evenings - star gazing is simply magical! We are certain that you’ll have a hard time leaving!

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Guest favorite

A serene landscape shows several Jersey cows grazing on lush green grass near a pond. The water reflects the blue sky and distant mountains, while the surrounding trees add depth to the tranquil rural setting.

Farm stay in Fairfield

4.98 out of 5 average rating, 333 reviews

Organic Farm Hideaway Home and Pond

The house is tucked into the back of our 300-acre working dairy farm and offers breathtaking views of Mt. Mansfield. We are located in between two of Vermont's best ski resorts, Jay Peak and Smuggler Notch. Come for a winter adventure full of downhill skiing, riding or x-country touring. Stay for the local breweries, distilleries and restaurants. Or just relax at the farm, cozy up by the wood stove and cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

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Top guest favorite

Two unique chalet structures, designed with a modern aesthetic, are situated on a sloped landscape. The buildings feature angular shapes and large glass windows, which reflect the surrounding forest, inviting nature indoors. The ground is covered with natural foliage and rocks.

Chalet in West Bolton, Quebec

4.99 out of 5 average rating, 255 reviews

La Binocle: Peaceful Architect Cottage

Cosy timeless chalet conceptualized by the architects of _naturehumaine. Nestled into the cliffside at an altitude of 490 meters (1600 feet), its unique design is distinguished by boldness and originality and fits with harmony in its environment. Surrounded by forest, the cottage offers breathtaking views of Mount Glen and the surrounding nature largely protected by the Appalachian Corridor. The perfect silent place to relax and unwind. Photo: Adrien Williams / S.A. CITQ #302449

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Guest favorite

The exterior of The 1860 Farmhouse is showcased, featuring a blue clapboard facade with white trim. A spacious porch extends along the front, with multiple gabled roof peaks. Lush green lawns surround the house, complemented by colorful flower beds and a glimpse of the countryside in the background.

Home in Berkshire

4.94 out of 5 average rating, 169 reviews

1860 Farmhouse

Enjoy a restful getaway at The 1860 Farmhouse. We purchased the farmhouse in 2018 from a family that had done extensive renovations to the interior. Keeping true to its historic roots, the farmhouse offers modern amenities in a historic setting. A convenient location close to Jay Peak and Smuggler's Notch, and many Vermont and Quebec attractions within an easy drive. Swiss and Bloom wedding venue and Phoenix Manor are close by. The house is 6 bedrooms and sleeps 12 people.

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Top guest favorite

Home in Richford

4.99 out of 5 average rating, 162 reviews

Peaceful + Cozy Farmhouse Near Jay Peak + Sutton

Our guest farmhouse, located 1 mile from the Canadian border, is close to Jay Peak Ski Resort and Mount Sutton. Mountain and meadow views are spectacular! Here, you are perfectly poised to explore both the quaint, foodie-focused, Eastern Townships just across the border in Quebec AND the scenic back-roads, abundant lakes, family farms, mountain trails, local pubs, and old general stores of Northern Vermont. Or just enjoy the porch & peaceful atmosphere!

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Guest favorite

Cottage in Dunham

4.95 out of 5 average rating, 146 reviews

Lovely Selby Lakeside Cottage

Lovely cottage on Lake Selby's shore with all the necessary facilities for a restful stay. - fully equipped kitchen (dishwasher included) - bathroom with cabin shower (no bath) - small bedrooms for maximum 4 - kayaks and pedalboat - outside firepit and inside fireplace (winter only) - wifi with unlimited download (high speed) - few minutes from commodities and Dunham village - close to Route des vins, Brasserie Dunham and mounts (Sutton and Bromont)

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Top guest favorite

A lone fisherman is silhouetted in a kayak, cast against the backdrop of a vibrant sunset over the calm waters of Lake Champlain. The sky features warm hues of orange and gold, reflecting softly on the water's surface.

Guesthouse in Highgate

4.97 out of 5 average rating, 770 reviews

Beautiful lake-front cottage, Lake Champlain

Lakefront cottage located in Highgate Springs, Vermont, on the Canadian border. The 2-bedroom cottage sits adjacent to the owner-occupied main house, on a large one-acre lot, with 120 feet of Lake Champlain shoreline. Enjoy the stunning sunset views while sitting on the deck overlooking the water. Private dock included. Montreal and Burlington each 45 minutes away. Available level-2 car charger. Well-behaved pets allowed. Super-fast WIFI!

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Top guest favorite

A log cabin exterior is covered in fresh snow, with a wooden ramp leading to the entrance. Snowbanks are piled high on either side of the walkway, creating a serene winter scene. The porch is supported by sturdy wooden columns, complementing the rustic setting.

Cabin in Berkshire

4.99 out of 5 average rating, 102 reviews

Rustic Log Cabin in Berkshire, Vermont

Welcome to 94 acres of serenity. This quiet, cozy log cabin is an easy 25 minute drive to the Jay Peak Ski Area. Come home and sit by the fire after a day on the slopes or splashing at the waterpark. Or stay in and cook in the fully-equipped kitchen. Bring your snow boots to explore the trails in the woods. Wifi and Direct TV included. Enosburgh Falls Village, 5 miles away, offers groceries, restaurants, banks and more.

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Guest favorite

A spacious living area features large windows allowing natural light to fill the space. A wood stove is positioned beside a modern, blue sofa. A dining table with green chairs occupies the center, complemented by wooden cubes that serve as additional seating.

Chalet in Sutton

4.96 out of 5 average rating, 274 reviews

Le chalet des bois, Peace and calm in the woods

Monumental open concept, in the heart of nature. Access to trails directly behind the house. Wood stove, large modern bathroom, one bedroom + sofa bed. Another sofa bed in the living room. Ideal chalet for a couple with children or two couples. Wild birds, turkey, and deer lovers welcome! Wifi and EV charger included. Dogs Welcome! CITQ : #308038

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