Holiday rentals in Berkshire

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.

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.

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!

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!

Cozy Vermont Home Near Jay Peak & Wedding Venues

Enjoy stunning sunrises over Jay Peak from this 3BR, 2BA home in Berkshire, VT. This spacious home offers a large deck with mountain views and modern, cozy comforts. Just 25 mi. to Jay Peak Ski Resort & nearby wedding venues, Swiss & Bloom, Berkshire Barn & Gardens and The Abbey. 5 mi. from Canada—perfect for day trips to Montreal. Golf, skiing, wineries, Lake Carmi State Park, scenic bike trails, hiking, local breweries, relaxation and adventure awaits. A perfect year-round Vermont getaway!

The Berkshire House - Spacious Farmhouse

Our huge 1860s farmhouse offers both privacy and gathering space with 7 bedrooms, great room, sitting room, large dining room, in 3800 SF. Recent whole-house renovations include a new kitchen, 3 full baths, 2 half baths, and multiple safety features. A private backyard and spacious decks offer beautiful pastoral views. Accommodates up to 16 people comfortably; minutes to Jay Peak, Smugglers Notch, Swiss & Bloom, St. Albans, rail trails, and many other Vermont and Quebec destinations

Cozy Cabin in a Cabin • Near Jay Peak Ski Resort

Our cabin would be a great getaway this summer or fall. Come and enjoy our beautiful space and RELAX ! Have you ever stayed in a cabin inside a cabin? This might be a first for you! The original structure was built over 40 years ago, and if you look closely, you’ll still see the original log walls beautifully featured as the heart of the home. Over time, the cabin has evolved, reflecting the lives and stories of those who’ve called it home — and we think that’s part of its magic.

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.

The Farmhouse

Circa 1850s fully renovated Vermont farmhouse less than 15 miles from Jay Peak Nestled in the mountains, yet conveniently located on a main road, this farmhouse has been family owned since 1970, with a completed total renovation in 2022. The property features 4 bedrooms with a total of 6 beds, and 2 bathrooms, with all new appliances for your comfort. Come enjoy rocking chairs on the front porch facing the mountains or a cozy fire pit in the back with a nearby babbling brook.

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!

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!

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)!