Holiday houses in Berkshire

4.99 out of 5 average rating, 157 reviews

Cabin in Enosburg

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!

4.94 out of 5 average rating, 117 reviews

Cabin in Montgomery

Mountain Retreat On The Creek

The Jay Peak Retreat - Experience the Northeast Kingdom’s premier destination at Jay Resort, known for its record breaking snowfall and Vermont’s largest indoor waterpark. Upon arrival, welcomed by an open-concept layout perfect for intimate gatherings and après-ski relaxation. The cabin blends high-end resort luxury with tranquility and privacy. Inquire about our Speak Easy Cabin, 15 minutes away. Conveniently located 1 hour from Burlington, 2 hours from Montreal, and 3.5 hours from Boston.

4.99 out of 5 average rating, 141 reviews

Home in Richford

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!

4.96 out of 5 average rating, 403 reviews

Farm stay in Fairfield

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!

4.95 out of 5 average rating, 148 reviews

Home in Berkshire

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.

4.91 out of 5 average rating, 127 reviews

Chalet in Saint-Armand

Nice pied-à-terre, perfect for visiting the area.

In St-Armand🇨🇦, a small house ideal as a pied-à-terre for visiting the area/wine route. 3 km from the border, near 133, it allows you to visit Vermont without sleeping in the United States. With a bedroom (double bed + single inflatable mattress), a living room with smart TV without cable for your subscriptions (Netflix…), a well-equipped kitchen, bathroom/shower and a dining room. There is double parking. It's a modest house near the neighbors and the noisy road.

4.95 out of 5 average rating, 145 reviews

Tiny home in Mansonville

La Cabine Potton

The cabin is a mini Scandinavian-style chalet that will appeal to lovers of nature, calm and ski slopes in winter as well as cycling and hiking in summer. This chalet was designed in harmony with its environment. Moreover, its size allows you to enjoy nature while reducing its ecological footprint. With its two bedrooms, fireplace, large terrace and hot tub, it is fully equipped to meet your needs. Come and relax in this unique place! CITQ Certificate #311739

4.8 out of 5 average rating, 125 reviews

Apartment in Sutton

In the heart of Sutton!

Nice accommodation in the heart of Sutton within walking distance to restaurants, shops, bakeries and cafes. Very bright! The room is quiet even though located in the city center. Perfect for couples and solo travelers. 5-minute drive to Mont Sutton! Dunham - 20 minutes - small village, Dunham Brewery, Wine Route Frelighsburg – 20 minutes – small picturesque village, restaurants and shops Bromont - 20 minutes - skiing, mountain biking, restaurants and shops

4.97 out of 5 average rating, 667 reviews

Guesthouse in Highgate

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!

4.92 out of 5 average rating, 477 reviews

Tiny home in Mansonville

Charming Tiny House bord de l'eau

Discover our charming Tiny House, ideal for a cozy stay by the river. Enjoy trails on the site and private access to the water. This project, lovingly designed, reflects our happiness to have a safe haven to recharge and practice outdoor activities. We want to share this experience with those looking for a sweet moment of wellness in the countryside. Treat yourself to a moment of serenity, alone or in love, in our little cocoon.

4.92 out of 5 average rating, 173 reviews

Apartment in Montgomery

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)!

4.81 out of 5 average rating, 178 reviews

Loft in Frelighsburg

Grain de Beauté de Frelighsburg CITQ: 296265

King bed available!Apartment with kitchen table, mini kitchenette, full bathroom. Free parking next to the building. This property is located in the heart of the village, on the Wine Route, within walking distance of the grocery store, opposite the Lyvano restaurant and a 2-minute walk from Beat & Betteraves. Go hiking on the FR1 or FR2 trails. 20 minutes drive to Sutton ski mountain and 35 minutes to Bromont.

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Other great holiday rentals in Berkshire

5 out of 5 average rating, 6 reviews

Treehouse in Johnson

Designer A-Frame Treehouse w/hot tub on river

JackieRating, 5 stars3 days ago

Tyler's A-Frame treehouse was exactly as described—an enchanting retreat nestled by the river. It had everything we needed for a perfect stay. The bed was exceptionally comfortable, and we particularly enjoyed starting our mornings on the spacious deck, sipping coffee and relaxing with a good book. It's just a short drive from Stowe, where you'll find a great selection of restaurants and shops. Overall, we highly recommend Tyler’s A-Frame treehouse for anyone looking for a peaceful getaway!

4.98 out of 5 average rating, 51 reviews

Home in Abercorn

Modern, clean, natural light filled chalet

PamelaRating, 5 stars1 day ago

Outstanding and Sophisticated Decor A Host Who Tries Very Much to Please

5 out of 5 average rating, 5 reviews

Chalet in Potton

Chalet Black Box – A sleek, modern retreat in nat

RobertRating, 5 stars3 months ago

Interesting location right on the US/Canada. The house is really nice, very neat and clean. Imagine IKEA. The road can be muddy and the location can be a bit isolated. 15 minutes away is Owl's Bread! Amazing baked goods and sandwiches. Across the park is a coffee shop with incredible lattes. If you have the time stop by the Bolton Spa for some relaxation. Definitely a cool spot. Read the history of Space Research Corporation. This house is on the 6000 acre campus.

5 out of 5 average rating, 35 reviews

Home in Sutton

Cozy eco-friendly house in Sutton

VincentRating, 5 stars1 month ago

Etienne and Kim's house was perfect for a quiet weekend with friends. The place is warm, relaxing and welcoming.

4.87 out of 5 average rating, 30 reviews

Tiny home in Richford

Tiny Cabin Giant Property-10 acres all to yourself

PaceRating, 5 stars1 month ago

The cabin is in a beautiful location and you will feel very secluded. The cabin is small but comes with pretty much everything you need and Jeff provided pots, pans, utensils, etc. so the only thing I had to do was grab some groceries before my stay. Super quiet and peaceful. If you’re looking to disconnect and get into the woods, this is the place for you

4.85 out of 5 average rating, 33 reviews

Yurt in Johnson

Grandview Yurt

HarrisonRating, 5 stars5 days ago

My only complaint is that we couldn't stay longer. Although we only stayed a night, it was very well worth the stay and value. The yurt was comfortable and cozy, and the nature in the area was really relaxing. If I ever find myself traveling through again, I would definitely stay at the Yurt again. Definitely recommended.