Vacation rentals in Berkshire

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Top-rated vacation rentals in Berkshire

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Guest favorite

Cabin in Enosburg

4.99 out of 5 average rating, 125 reviews

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!

Superhost

Cottage in Dunham

4.86 out of 5 average rating, 187 reviews

Ski & Spa Chic Cozy Cottage, Selby Lake Dunham

Your own cottage has 2 bedrooms nearby the lake! Relax in your private suite & spa after a day on the hill biking on majestic Mont Pinacle or touring the vineyards on the famous Route des vins. Unwind on our spacious terrasse with Spa, 2 BBQ's and table sitting 6 comfortably. Located only 60 min from Montreal, a perfect romantic spot for 1 or 2 couples with kids and pets. Skiers will hit the slopes in Sutton and Bromont just 30 min away. Enjoy the Eastern Townships at its best! CITQ: 307418

Guest favorite

Home in Richford

4.99 out of 5 average rating, 123 reviews

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!

Guest favorite

Farm stay in Fairfield

4.96 out of 5 average rating, 375 reviews

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!

Guest favorite

Home in Berkshire

4.94 out of 5 average rating, 139 reviews

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.

Guest favorite

Guest suite in Sutton

4.95 out of 5 average rating, 130 reviews

Guest Studio with Beautiful Mountain Views

Our 30 acre farm property is located on a quiet country road just 6 kms from Sutton Village, a haven for cyclists, hikers, skiers and wine enthusiasts. The village features 2 brewpubs, a good choice of restaurants, fun shops and beautiful Mt. Sutton to explore. Enjoy spectacular views and sun rises from your private balcony or patio, cycle along the surrounding backroads or just enjoy some quiet time in front of the wood burning stove or outdoor fire pit.

Guest favorite

Rental unit in Sutton

4.95 out of 5 average rating, 304 reviews

Sutton - Large terrace - 10 min to the mountain

Located in the middle of nature and only a few minutes from the village of Sutton, nice independent 4-season apartment - same as the hosts' main house. Completely equipped. Large outdoor terrace for exclusive use by visitors and BBQ to enjoy the beautiful summer and autumn evenings. 10 minutes from Sutton ski resort and its many activities. Bicycle, skiing, golf, hiking, kayaking, wine route. Tranquility and bird songs guaranteed! Property number 296758

Guest favorite

Cottage in Dunham

4.95 out of 5 average rating, 106 reviews

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)

Guest favorite

Home in Dunham

4.84 out of 5 average rating, 186 reviews

La DUNHAM LAKE CABIN - Lake, Vineyards, Cycling

Located in a peaceful area and at 4 minute walk from our lake access, The Dunham Lake Cabin is a place that inspires rest, relaxation and rejuvenation as a couple, alone or with friends. You will undoubtedly be charmed by each of the small rooms in this cabin. Fully equipped, kayaks, fireplace, fire pit, Adirondack chairs, outdoor table protected from the rain, BBQ and 3 cozy and comfortable beds, you won't miss anything! Capacity up to 6 people.

Guest favorite

Guesthouse in Highgate

4.97 out of 5 average rating, 606 reviews

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!

Guest favorite

Cottage in Dunham

4.97 out of 5 average rating, 184 reviews

Cozy Little Orchard House in Dunham

This newly built house is located on our 90 acre property. It is surrounded by an orchard, a vineyard and forest. The quaint and natural setting is perfect for couples, solo travellers or families. Cross country skiing, running and hiking can be practiced on the property. Bromont and Sutton downhill ski slopes are a 35 minutes drive away. Jay Peak, Vermont is 1h15 away by car. The surrounding country roads provide for wonderful bike rides.

Guest favorite

Chalet in Frelighsburg

4.91 out of 5 average rating, 321 reviews

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