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Holiday rentals in Berkshire

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Top-rated holiday rentals in Berkshire

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

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Top guest favourite
Cabin in Enosburg
4.99 out of 5 average rating, 181 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. When morning comes, enjoy your coffee while cozied up in front of the fireplace. Or simply stay in bed and admire the view. With plenty of land to explore, a hike is always welcome. The choice is yours!

Top guest favourite
A serene outdoor space features a patio table surrounded by chairs, set against the calm waters of Metcalf Pond. A large umbrella provides shade, while an American flag gently flutters nearby. The backdrop includes rolling hills adorned with autumn colors.
Cottage in Fletcher
5 out of 5 average rating, 163 reviews

Metcalf Pond Camp Convenient to Smugglers Notch

Handcrafted cozy waterfront camp on Metcalf pond. Propane fireplace provides for welcome warmth after fall or winter adventures. Soak in the Hot tub on the deck. Custom spiral staircase accesses carpeted sleeping loft with books, TV, rocking chair. Enjoy the quiet off season brings to the area when most camps are shuttered for winter. Enjoy staying in and cooking and taking in the cozy atmosphere or make the approximately 20 minute drive to Smugglers Notch or enjoy other local attractions.

Top guest favourite
A serene winter landscape displays gently rolling snow-covered hills, with distant mountains rising under a clear blue sky. Small structures are scattered across the meadow, surrounded by sparse trees, creating a peaceful and open atmosphere.
Home in Richford
4.99 out of 5 average rating, 156 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 from every window! Here, you are perfectly poised to explore both the quaint, foodie-focused, French-Canadian, 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!

Top guest favourite
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
4.99 out of 5 average rating, 202 reviews

The Binocular: 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

Top guest favourite
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
4.95 out of 5 average rating, 154 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.

Top guest favourite
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
4.95 out of 5 average rating, 151 reviews

Jay Peak Retreat

The Jay Peak Retreat – Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This warm, stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski lounging. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, patio, fire pit, and plush outdoor chairs. Just 1 hour from Burlington, 2 from Montreal, and 3.5 from Boston.

Guest favourite
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, 233 reviews

Le chalet des bois, Peace and calm in the woods

*$* WINTER PROMOTION *$* For a weekend reservation (Fri. & Sat.) the 3rd night on Sunday is $90.00!. 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

Top guest favourite
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.
Guest house in Highgate
4.97 out of 5 average rating, 710 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!

Top guest favourite
A spacious living and dining area features a wooden dining table surrounded by chairs. A floral-patterned sofa and a futon provide seating, complemented by a wooden coffee table. Natural light enters through multiple windows, enhancing the warm wooden accents throughout the space.
Cottage in Dunham
4.98 out of 5 average rating, 211 reviews

Cozy Little Orchard House in Dunham

This newly built house is located on our 90 acre property. It is surrounded by an orchard, a vineyard and forest. The quaint and natural setting is perfect for couples, solo travellers or families. Cross country skiing, running and hiking can be practiced on the property. Bromont and Sutton downhill ski slopes are a 35 minutes drive away. Jay Peak, Vermont is 1h15 away by car. The surrounding country roads provide for wonderful bike rides.

Guest favourite
A bright and airy kitchen space is visible, showcasing a blend of white cabinetry and natural textures. A round dining table with a woven centerpiece is prominently displayed. Soft light enhances the serene ambiance, while a woman in a stylish outfit walks gracefully towards an open doorway.
Cottage in Dunham
4.85 out of 5 average rating, 221 reviews

Dunham Lake Cabin - Lake, Vineyards, Cycling

Just a 4 minute walk from lake access, The Dunham Lake Cabin is the perfect retreat for relaxation and adventure. Ideal for couples, solo travellers, or family, this charming and fully equipped cabin offers three cozy beds, a fireplace, paddle board, a fire pit, Adirondack chairs, and a covered outdoor dining area with a BBQ. Unwind in nature, paddle on the lake, or gather around the fire for a memorable stay.

Top guest favourite
The A-frame house is surrounded by a winter wonderland, with snow-covered trees and a blanketed yard. Sunlight reflects off the snow, enhancing the serene atmosphere. The house features large front windows and a balcony, creating a welcoming exterior in this peaceful, snowy setting.
Loft in Sutton
5 out of 5 average rating, 271 reviews

Loft des Marmites

CITQ #306547 Tourisme Québec Cozy and private loft on Mont Sutton, surrounded by trees, in a very quiet and peaceful area, yet 2 minutes away from the ski and mountain bike station as well as the P.E.N.S. hiking trails (Parc d'Environnement Naturel de Sutton). The Round Top trail leads to the summit with a fabulous view of the region, and a excellent panorama of Jay Peak and the "Green Mountains of Vermont".

Top guest favourite
The exterior of the charming studio is surrounded by lush greenery and vibrant flowering plants. Large glass doors offer a glimpse into the interior, while a gravel pathway guides visitors to the entrance. A wooden railing lines the pathway, adding to the welcoming atmosphere.
Place to stay in Sutton
4.95 out of 5 average rating, 243 reviews

Between village and summit – pet-friendly

Charming studio with a private entrance, situated on a semi-private dead-end street in a tree-filled, quiet neighborhood. Located near Maple Street, it’s just a 5-minute drive from Mont Sutton and 2 minutes from the village. Close to hiking trails, 5 minutes by car from Mont Sutton and 2 minutes from the village. A very friendly Standard Poodle is on site.

Popular amenities for Berkshire holiday rentals

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