Vacation rentals in Berkshire

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!

Meadow Cottage on Organic Farm with Mountain Views

The Meadow Cottage is perched on a picturesque knoll in the back of our 300 acre working dairy farm. 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, restaurants and antique stores. Or just relax at the farm, watch us milk the cows or cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

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.

Charmante Tiny House bord de l'eau

Découvrez notre charmante Tiny House, idéale pour un séjour chaleureux au bord de la rivière. Profitez de sentiers sur le site et d’un accès privé à l’eau. Ce projet, conçu avec amour, reflète notre bonheur d’avoir un havre de paix où se ressourcer et pratiquer des activités de plein air. Nous souhaitons partager cette expérience avec ceux qui recherchent un doux moment de bien-être en campagne. Offrez-vous un moment de sérénité, seul ou en amoureux, dans notre petit cocon.

Mountain Retreat On The Creek

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.

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

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)!

Frelighsburg. Charming mountain log pavillon

This authentic 4 season log cottage with its large stone fireplace and 2 bedrooms can accommodate 4 people. Ideal for a couple with 2 children. Fully equipped. Large sunny terrace. BBQ. High Speed Wifi. An ideal place for nature lovers, for biking, hiking, skiing or just relaxing. A haven of peace and inspiration for writers, poets at heart and dreamers... Quebec Tourism Reference number : 297222

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.