Holiday rentals in Berkshire

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!

Cabin in the Woods VT - Discount Jay Peak Lift Tix

Come enjoy the ski season and a relaxing weekend at our private guest cabin in the woods. A brook flows through the backyard, providing a peaceful natural backdrop and a stone outdoor fire pit for great campfire fun. The main floor bedroom has 1 queen bed and the loft has 1 queen and 1 twin. There is also a living room couch. Just 5 min to town, 15-20min to Jay Peak! Use our vouchers for discount lift tickets! **We recently added “The Loft” listing on the other side of the same property**

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 stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

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

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.

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, 35 minutes to Sutton Quebec!!

Hidden Chalet 8 minutes from Jay Peak

This one of a kind property, formerly a Historic Grist mill (with ruins still on the property to explore) is surrounded on 3 sides by the Jay Branch River, a crystal clear mountain stream that runs down from Jay peak. The property is filled with Cedar and Maple and the sound of the River permeates through the trees. With multiple swimming holes and a 20 foot waterfall just steps from the deck there’s not another Airbnb like this in the state of Vermont.

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)

Dog Friendly Apartment near Jay Peak

Enjoy the beauty of Montgomery, Vermont while staying in a very spacious 1-bedroom apartment that is attached to an 1880s farmhouse with a large backyard, garden and and orchard. The apartment is a 15-20 minute drive to Jay Peak Resort and a 3 minute drive to a grocery store and restaurants. It is walking distance from the Hutchins covered bridge and there is private access to the river. Excellent walking for your dog(s)!

Vermont Getaway Cabin

Ski the East while staying just minutes away from Jay Peak! The perfect Vermont getaway! Enjoy the peacefulness of our 4 season camp on private 23 acres of land, and conveniently located to Vermont mountains, lakes, rivers, hiking trails, VAST trail and ATV access. No smoking. No pets. No third party bookings without prior permission.