
Holiday houses in Berkshire
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Top-rated holiday rentals in Berkshire
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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!

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.

Hillwest Mountain View
We are close to Jay Peak and Canada including Montreal. If you like hiking, the Long Trail is close by. If you like star gazing you will love seeing the Milky Way in our backyard. Our house is good for both couples and families. We have a private hiking trail that leads down to a cool mountain stream where you can cool off. Take a dip in the nearby Hippie Hole or go fishing or canoeing in nearby lake Carmi. There are three bedrooms and a master bath with a spa tub. Wifi, fireplace and more.

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.

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!

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!

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

The Book Barn: Newly Renovated Guesthouse
Enjoy all Vermont has to offer in this bright, airy space minutes away from Burlington and the mountains. On 14 acres with a brook, it’s a short walk down a dirt road to a historic covered bridge and town common. Fall colors are breathtaking when taken in from the barn deck, while Spring and Summer visitors enjoy free concerts on the town green on Sundays. Spectacular sunsets and hot air balloons are familiar sights. It doesn’t get much more Vermonty. *Note: No Cleaning Fee!

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.

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)

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!

The Country House in the Mountains
Spacious and private chalet, 5 minutes from the ski slopes and the magnificent village of Sutton. Access to your own spa on the terrace, which is open 3 seasons. Private lot with a birch forest at the back of the chalet, wood fireplace in the living room to relax, outdoor fireplace, swimmable pond with pure water sourced from the mountain. Tranquility assured!
Popular amenities for Berkshire holiday rentals
Other great holiday rentals in Berkshire

Luxury Converted Country Church

The Farmhouse

Coeur du village CITQ: 296265

Modern, clean, natural light filled chalet

The Berkshire House - Spacious Farmhouse

Peaceful Farm Stay w/Mountain Views & Stargazing

Shadow Lake house

Ecological cabin forest retreat in Frelighsburg
Destinations to explore
- Plainview Holiday rentals
- Tuckahoe Holiday rentals
- Long Island Holiday rentals
- Boston Holiday rentals
- East River Holiday rentals
- Hudson Valley Holiday rentals
- Québec City Holiday rentals
- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Island of Montreal Holiday rentals
- Erie Canal Holiday rentals
- East Side Holiday rentals
- Jay Peak Resort
- Owl's Head
- Mont Sutton Ski Resort
- Ski Bromont
- Jay Peak
- Zoo de Granby
- Bolton Valley Resort
- Jay Peak Resort Golf Course
- Pump House Indoor Waterpark
- Stowe Mountain Resort
- ECHO, Leahy Center for Lake Champlain
- University of Vermont
- Shelburne Museum
- Boyden Valley Winery & Spirits
- Shelburne Vineyard
- Bleu Lavande
- Quartier Dix30
- Mont-Orford National Park
- Lake Champlain Chocolates
- Waterfront Park
- Spa Bolton
- Kingdom Trails
- Snow Farm Vineyard & Winery
- Marais de la Rivière aux Cerises




