Vacation rentals in Berkshire

Jay Peak Retreat

Jay Peak Retreat, Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This cabin offers an open-concept layout perfect for cozy gatherings and après-ski. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, fire pit, outdoor furniture. 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!! Four ski resorts nearby of the cabin Jay, Smuggs, Stowe, Mont Sutton!

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!

La Binocle: 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

Scandi Cabin • Expansive Deck & Green Mtn Views

A Scandinavian cabin where floor-to-ceiling windows frame sweeping views across Vermont’s Green Mountains and the Missisquoi River Valley. Maison Alice is one of two thoughtfully positioned cabins on our four-acre hillside, each with its own entrance and outdoor living spaces. This is a place where it’s easy to slow down. Some mornings begin with coffee on the deck. Others with a walk through the meadow. Either way, there’s no hurry. Outside has a way of becoming part of the day.

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!

Rustic Log Cabin in Berkshire, Vermont

Welcome to 94 acres of serenity. This quiet, cozy log cabin is an easy 25 minute drive to the Jay Peak Ski Area. Come home and sit by the fire after a day on the slopes or splashing at the waterpark. Or stay in and cook in the fully-equipped kitchen. Bring your snow boots to explore the trails in the woods. Wifi and Direct TV included. Enosburgh Falls Village, 5 miles away, offers groceries, restaurants, banks and more.