Holiday rentals in Berkshire

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Top-rated holiday rentals in Berkshire

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

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Guest favourite

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.

15–22 Sep

$98 SGD per night

Guest favourite

Home in Montgomery, Vermont, US

4.96 out of 5 average rating, 116 reviews

Hillwest Mountain View

We are close to Jay Peak and Canada including Montreal. If you like hiking, the Long Trail is close by. If you like star gazing you will love seeing the Milky Way in our backyard. Our house is good for both couples and families. We have a private hiking trail that leads down to a cool mountain stream where you can cool off. Take a dip in the nearby Hippie Hole or go fishing or canoeing in nearby lake Carmi. There are three bedrooms and a master bath with a spa tub. Wifi, fireplace and more.

5–12 May

$237 SGD per night

Guest favourite

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.

5–12 Feb

$110 SGD per night

Guest favourite

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!

7–14 Oct

$196 SGD per night

Guest favourite

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!

29 Mar – 5 Apr

$193 SGD per night

Guest favourite

Cabin in Montgomery, Vermont, US

4.92 out of 5 average rating, 189 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.

11–18 Oct

$132 SGD per night

Guest favourite

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 is only 15 minutes away. The house is 6 bedrooms and sleeps 12 people.

25 Jan – 1 Feb

$345 SGD per night

Guest favourite

Flat in Sutton, Canada

4.96 out of 5 average rating, 276 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 - in the same main house of the hosts. Fully 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. Cycling, skiing, golf, hiking, kayaking, wine route. Peace and quiet and birdsong guaranteed ! Establishment Number 296758

16–23 Dec

$154 SGD per night

Guest favourite

Cottage in Dunham, Canada

4.87 out of 5 average rating, 122 reviews

Small warm cottage with spa and lake access!

It's called Lake Selby's gem! This small, warm, minimalist, welcoming yellow cottage will offer you an inspiring space to drop you off, work remotely, or spend time as a couple, with friends, or with family, away from the distractions of everyday life, and close to nature. Spa, canoe, paddle board, forest steps, candlelit meal, campfire and much more! That's what's waiting for you here! Minutes from the microbrewery, restaurants, and bakery!

28 Sep – 5 Oct

$153 SGD per night

Guest favourite

Guest house in Highgate, Vermont, US

4.98 out of 5 average rating, 528 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!

4–11 Apr

$149 SGD per night

Guest favourite

Chalet in Frelighsburg, Canada

4.91 out of 5 average rating, 298 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

4–11 Dec

$151 SGD per night

Guest favourite

Cottage in Dunham, Canada

4.98 out of 5 average rating, 172 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.

21–28 May

$120 SGD per night