Some info has been automatically translated. Show original language

Holiday rentals in Berkshire

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Berkshire

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

1 of 1 pages1 / 1
Top guest favourite
The cozy mountain home is surrounded by a vibrant autumn landscape, featuring trees in hues of orange, red, and yellow. Rolling mountains can be seen in the background, with a winding gravel path leading to the house, inviting exploration of the natural beauty.
Home in Westfield
4.96 out of 5 average rating, 253 reviews

Jay Peak 3 miles - secluded with spectacular view!

Mountains, streams & seclusion! • Hike the Long Trail • Road, gravel & mountain biking • Jay Peak Resort is three miles away! • Waterpark • Golf • Backcountry guiding - hiking, kayaking, gravel & mountain biking (15% discount) • Photography and videography (15% discount) This is the mountain getaway you dream about! Our only neighbors are animals in the surrounding mountains & forests. Note: There is also an apt in the main house that sleeps 8. Welcome to Vermont Mountain Experience!

Top guest favourite
A charming cedar shake cottage features a light-colored facade with large windows framed by greenery. A stone pathway leads to the white front door, surrounded by tasteful landscaping including bushes and flowers. The property is set within a grassy area, providing a spacious feel.
Cottage in Montgomery
4.97 out of 5 average rating, 122 reviews

Charming Cottage by Jay Peak

Quaint cedar shake cottage perfect for a couples getaway. Bright open floor plan, comfortable and tastefully furnished. Gas fired stove in living room provides warmth and ambiance while the queen size bed is incredibly comfortable. Great galley kitchen fully equipped with everything you need to prepare your favorite meal or if you're not in the mood to cook there's four restaurants within walking distance. Jay Peak is only 8 miles from door to door. Easy parking. Discount ski tickets available.

Top guest favourite
A modern treehouse features a warm wooden exterior, elevated on a platform among vibrant autumn foliage. Large glass windows provide a view into the inviting interior space. Steps and a small deck lead to seating arranged on the ground level, surrounded by natural scenery.
Treehouse in Newport
4.97 out of 5 average rating, 315 reviews

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.

Top guest favourite
Home in Richford
4.99 out of 5 average rating, 159 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!

Top guest favourite
A serene landscape is displayed, featuring layered mountains in the distance partially shrouded in morning mist. A bright blue sky punctuated with wispy clouds creates a tranquil backdrop, while lush green trees are visible in the foreground.
Farm stay in Fairfield
4.97 out of 5 average rating, 449 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!

Top guest favourite
An open concept living space features a large sectional sofa and a coffee table centered on a textured area rug. Expansive windows allow natural light to fill the room, showcasing views of the surrounding mountains and greenery. A dining table with chairs is positioned nearby.
Cabin in Enosburg
4.99 out of 5 average rating, 196 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 stay in bed and take in the views. And with plenty of woods to explore, it's your perfect escape at your pace.

Top guest favourite
The chalet is nestled among greenery, featuring a modern design with multiple interconnected sections. Large windows provide views of the surrounding forest. A seating area with a parasol, located outside, enhances the serene atmosphere.
Chalet in West Bolton
4.99 out of 5 average rating, 233 reviews

The Binocular: 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

Top guest favourite
A spacious kitchen features wooden cabinetry and a variety of modern appliances. A large island is complemented by bar stools, and natural light filters through nearby windows, providing a warm and inviting space. Exposed wooden beams add to the farmhouse charm.
Home in Berkshire
4.95 out of 5 average rating, 165 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.

Top guest favourite
An outdoor patio area features two wooden lounge chairs facing a central table, surrounded by greenery. A cozy seating arrangement includes a modern sectional sofa and a distinctive round lounge chair. A barbecue grill is positioned nearby, with stone paving underfoot.
Cabin in Montgomery
4.94 out of 5 average rating, 175 reviews

Jay Peak Retreat

The Jay Peak Retreat – Experience the Northeast Kingdom’s premier destination at Jay Resort, known for record snowfall and Vermont’s largest indoor waterpark. This warm, stylish cabin offers an open-concept layout perfect for cozy gatherings and après-ski lounging. Blending upscale comfort with rustic charm, enjoy a creek out back, river across the street, patio, fire pit, and plush outdoor chairs. Just 1 hour from Burlington, 2 from Montreal, 35 minutes to Sutton Quebec!!

Guest favourite
A hot tub is set on a wooden deck, surrounded by tall trees and a lush green lawn. Nearby, a stack of logs is visible, along with two yellow chairs, creating a peaceful outdoor relaxation area.
Tiny home in Mansonville
4.96 out of 5 average rating, 198 reviews

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

Guest favourite
Cabin in Bakersfield
4.85 out of 5 average rating, 109 reviews

Modern 3-BD Mountain Cabin w/ Hot Tub, Deck, Loft

Take it easy at this unique and tranquil getaway in the quiet mountains of Vermont, off the beaten path yet near Jay Peak and Smuggler's Notch, within 45 minutes of Stowe (1 hour in the winter) and 45 minutes of Burlington. This bespoke, 2000+ sq ft luxury cabin, hand-built by local artisans, includes a brand-new hot tub and deck, a loft, a beautiful dining nook, and 28 acres of private land with trails on premises.

Top guest favourite
Yurt in Bakersfield
4.99 out of 5 average rating, 138 reviews

Secluded Cozy Yurt | Hot Tub + Mountain Views

Escape to this unique mountain retreat in Vermont. Relax in the Jacuzzi spa with stunning mountain views, or roast marshmallows around the outdoor fire pit. Perfect for a solo reset or a romantic getaway. Surrounded by nature and close to ski resorts, hiking trails, and local breweries. A modern, peaceful space to unwind, recharge, and enjoy the best of Vermont—whether you stay in or explore out.

Popular amenities for Berkshire holiday rentals

  1. Airbnb
  2. United States
  3. Vermont
  4. Franklin County
  5. Berkshire