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Holiday rentals in Berkshire

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Top-rated holiday rentals in Berkshire

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Top guest favourite
The exterior of the property is viewed from the gravel driveway, featuring a red barn-style section and a white house with multiple windows. The green lawn surrounds the house, and the lake is visible in the background, framed by trees.
Flat in Morristown
5 out of 5 average rating, 127 reviews

Private Getaway on Lake Lamoille

Tucked away on Lake Lamoille in Morristown, this beautiful brand new apartment is just minutes from town and yet offers tranquility and spectacular views. The lake is home to eagles, herons, geese, ospreys and fish! You will see kayakers out there fishing! Stowe Mt and Smuggler’s Notch are both nearby. Breweries, art galleries, restaurants are close by. You can walk or bike to the 93 mile Lamoille Valley Rail Trail from our home. Our shed is available for storing your bikes, kayaks or skis.

Top guest favourite
A serene outdoor space features a patio table surrounded by chairs, set against the calm waters of Metcalf Pond. A large umbrella provides shade, while an American flag gently flutters nearby. The backdrop includes rolling hills adorned with autumn colors.
Cottage in Fletcher
4.99 out of 5 average rating, 174 reviews

Metcalf Pond Camp Convenient to Smugglers Notch

Handcrafted cozy waterfront camp on Metcalf pond. Propane fireplace provides for welcome warmth after fall or winter adventures. Soak in the Hot tub on the deck. Custom spiral staircase accesses carpeted sleeping loft with books, TV, rocking chair. Enjoy the quiet off season brings to the area when most camps are shuttered for winter. Enjoy staying in and cooking and taking in the cozy atmosphere or make the approximately 20 minute drive to Smugglers Notch or enjoy other local attractions.

Top guest favourite
A blue house with a pitched roof is set against a clear blue sky. Lush green grass surrounds the property, and trees provide a natural border. A person is seen walking across the spacious lawn, highlighting the outdoorsy setting.
Home in Montgomery
4.96 out of 5 average rating, 137 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.

Top guest favourite
Cabin in Morristown
5 out of 5 average rating, 250 reviews

Cady’s Falls Cabin

Welcome to our treehouse inspired, modern cabin overlooking The Kenfield Brook on Terrill Gorge. We are located 5 miles from Stowe and its attractions, and just a few minutes from downtown Morrrisville with all its amenities. Just upstream from the picturesque Cady’s Fall swimming hole and across the brook from the amazing Cady’s Falls bike trails, our cabin is perched atop the hillside. With its simple, minimalist design it’s easy to immerse yourselves in nature and feel at home in the trees.

Guest favourite
A serene landscape shows several Jersey cows grazing on lush green grass near a pond. The water reflects the blue sky and distant mountains, while the surrounding trees add depth to the tranquil rural setting.
Farm stay in Fairfield
4.98 out of 5 average rating, 325 reviews

Organic Farm Hideaway Home and Pond

The house is tucked into the back of our 300-acre working dairy farm and offers breathtaking views of Mt. Mansfield. 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 and restaurants. Or just relax at the farm, cozy up by the wood stove and cook up some delicious farm raised food for dinner. Well behaved dogs are welcome anytime!

Top guest favourite
A serene winter landscape displays gently rolling snow-covered hills, with distant mountains rising under a clear blue sky. Small structures are scattered across the meadow, surrounded by sparse trees, creating a peaceful and open atmosphere.
Home in Richford
4.99 out of 5 average rating, 156 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 favourite
The front exterior of a historical cottage is framed by lush green trees and blooming lilac bushes, providing a vibrant contrast against the structure. A small porch is visible, offering a view of the surrounding nature.
Cottage in Westfield
4.9 out of 5 average rating, 186 reviews

Historic Schoolhouse Minutes From Jay Peak

After a long day of hiking, biking, or skiing, come take a swing at our charming historical cottage. Dating back to the mid 1800s it was one of the first schoolhouses in the area, today it is filled with all the modern luxuries one would need. Our quaint porch is perfect for bird watching or leaf peeping. The inside includes high ceilings, a bedroom and a cozy loft- both with queen beds. French culture is only a 10 min drive away; Vermont culture is abound with maple syrup and warm locals.

Top guest favourite
A small vase containing vibrant flowers is placed on a wooden shelf. Sunlight filters through large windows, illuminating a loft area with a wooden ceiling. Spacious seating areas are visible below, providing a welcoming atmosphere.
Barn in Westford
5 out of 5 average rating, 283 reviews

The Book Barn: Newly Renovated Guesthouse

Enjoy all Vermont has to offer in this bright, airy space minutes away from Burlington and the mountains. On 14 acres with a brook, it’s a short walk down a dirt road to a historic covered bridge and town common. Fall colors are breathtaking when taken in from the barn deck, while Spring and Summer visitors enjoy free concerts on the town green on Sundays. Spectacular sunsets and hot air balloons are familiar sights. It doesn’t get much more Vermonty. *Note: No Cleaning Fee!

Guest favourite
A modern living area features a comfortable brown sofa beside a wooden coffee table. Exposed wooden beams run across the ceiling, while a staircase leads to an upper level. Natural light fills the space through large windows, creating a warm and inviting environment.
Cabin in Montgomery
4.93 out of 5 average rating, 165 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, and 3.5 from Boston.

Top guest favourite
A lone fisherman is silhouetted in a kayak, cast against the backdrop of a vibrant sunset over the calm waters of Lake Champlain. The sky features warm hues of orange and gold, reflecting softly on the water's surface.
Guest house in Highgate
4.97 out of 5 average rating, 723 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!

Top guest favourite
The exterior of a two-story chalet is shown, featuring large windows that reflect the surrounding trees. The structure is constructed with wooden materials, and a sloped roof extends over the outdoor terrace. Snow is visible on the ground, indicating a winter setting.
Chalet in Eastman
4.93 out of 5 average rating, 174 reviews

Beautiful ecological cottage near Mont Orford

Located 20 minutes away from the hills of the Mont Orford, this cottage has everything everything to charm you. You will find a living room with natural light, a cozy dining room, a fully equipped kitchen, two closed bedrooms and a glass mezzanine with a sofa bed. A patio (with BBQ), a huge terrace and the basement are also at your disposal. The chalet is eco-friendly. You can enjoy it with peace of mind!

Guest favourite
A modern living space features a cozy sofa facing a wall-mounted television. A minimalist fireplace is situated below, accompanied by a round side table and a soft area rug. Natural light floods in through large windows, enhancing the serene ambiance.
Chalet in Sutton
4.87 out of 5 average rating, 236 reviews

L'Hivernon – Scandinavian Inspiration

New build! This property has an open 1400 sq. ft. space with two bedrooms and two full baths. The accommodation is located on private land crossed by a river. With its oversized windows, 3 fully equipped outdoor terraces surrounded by nature and trees, this luxury villa is synonymous with comfort and connection to nature. You'll also have access to a private outdoor hot tub! The perfect romantic getaway!

Popular amenities for Berkshire holiday rentals

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