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

Guest suite in Sutton, Canada

4.93 out of 5 average rating, 104 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, the walking paths in our forest behind, cycle along the surrounding backroads or just enjoy some quiet time in front of the wood burning stove or outdoor fire pit.

Sep 18 – 25

G$14,774 GYD per night

Guest favorite

Cottage in Dunham, Canada

4.87 out of 5 average rating, 122 reviews

Petit chalet chaleureux avec spa et accès au lac!

On la surnomme la pépite du Lac Selby! Ce petit chalet jaune chaleureux, minimaliste, et accueillant vous offrira un espace inspirant pour vous déposer, travailler à distance ou passer du temps en couple, entre amis, ou en famille, loin des distractions du quotidien, et près de la nature. Spa, canot, planche à pagaie, marches en forêt, repas à la chandelle, feu de camp et bien plus encore! C'est ce qui vous attend ici! À quelques minutes de la microbrasserie, des restos et de la boulangerie!

Aug 9 – 16

G$23,005 GYD per night

Guest favorite

Guest suite in Sutton, Canada

4.95 out of 5 average rating, 218 reviews

Charming Studio close to Sutton's. Queen bed.

The studio is attached to our house, but very private. 2 miles from Sutton’s Village, 9 miles from the Us Borders. In the village you will find delicatessen,microbreweries , restaurants , art galleries , shops . It’s near ski centres, golf courses and spas. The area is known for its wine route , bike rides , hiking trails and local produces . Enjoy the atmosphere of the studio, the quality of its equipment , its brightness , its peaceful environment. Perfect for couples and solo travellers.

May 9 – 16

G$16,661 GYD per night

Guest favorite

Home in Richford, Vermont, US

4.99 out of 5 average rating, 117 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!

Jan 31 – Feb 7

G$29,475 GYD per night

Guest favorite

Apartment in Sutton, Canada

4.96 out of 5 average rating, 276 reviews

Sutton - Grande terrasse - À 10 min de la montagne

Situé en pleine nature et à seulement quelques minutes du village de Sutton, joli appartement 4 saisons indépendant - à même maison principale des hôtes. Complètement équipé. Grande terrasse extérieure à usage exclusif des visiteurs et BBQ pour profiter des belles soirées d'été et d'automne. À 10 minutes de la station de ski de Sutton et de ses nombreuses activités. Vélo, ski, golf, randonnées, kayak, route des vins. Tranquillité et chants d'oiseaux assurés ! Numéro d'établissement 296758

Apr 26 – May 3

G$23,992 GYD per night

Guest favorite

Farm stay in Fairfield, Vermont, US

4.97 out of 5 average rating, 327 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!

Jan 30 – Feb 6

G$29,063 GYD per night

Guest favorite

Home in Berkshire, Vermont, US

4.94 out of 5 average rating, 130 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.

Sep 1 – 8

G$52,902 GYD per night

Guest favorite

Cabin in Montgomery, Vermont, US

4.92 out of 5 average rating, 190 reviews

Remote yet convenient cabin

Escape to a remote yet convenient spot in the mountains. This cabin is an open space with a kitchen, bathroom, and loft bedroom. 1000 square feet of rustic coziness inside with all the conveniences. It is located on 15 acres with amazing views, walking/ hiking/ X country Skiing/ biking/ ATV/ snowmobiling options, foliage season, and a pond in the summer. While this cabin is situated outside of town, it is close to all the local restaurants and 20 minutes from Jay Peak Resort.

Oct 18 – 25

G$19,814 GYD per night

Guest favorite

Guest suite in Sutton, Canada

4.94 out of 5 average rating, 242 reviews

Tiny House in the heart of the village

Tiny house attached to our home in the heart in Sutton. After traveling extensively and using AirBnB we put a lot of thought into creating the exact type of space we would want to rent. Calm, relaxing, with little distraction for your vacation and most importantly a very comfortable bed. Walking distance to all Sutton has to offer and only a five minute drive to the Mont Sutton puts everything at your finger tips for your weekend away from the city. CITQ #: 305207

Aug 23 – 30

G$17,515 GYD per night

Guest favorite

Guesthouse in Highgate, Vermont, US

4.98 out of 5 average rating, 529 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!

Mar 6 – 13

G$22,452 GYD per night

Guest favorite

Chalet in Frelighsburg, Canada

4.91 out of 5 average rating, 299 reviews

Frelighsburg. Charming mountain log pavillon

SPECIAL RATE for APRIL & MAY: $99. 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

Sep 23 – 30

G$22,799 GYD per night

Guest favorite

Cottage in Dunham, Canada

4.98 out of 5 average rating, 173 reviews

Cozy Little Orchard House in Dunham

This newly built house is located on our 90 acre property. It is surrounded by an orchard 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.

Sep 17 – 24

G$18,050 GYD per night