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15 Aug - 17 Aug
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22 Aug - 24 Aug
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5 Sep - 7 Sep
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3 Oct - 5 Oct

Browse Select The Berkshires Cottages

Luxury Vacation Rental in the Berkshires!
Relax in a serene outdoor setting with a central fire pit surrounded by Adirondack chairs.

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
A-frame Cabin w/ Furnished Deck in Becket!
House (2 Bedrooms) | Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Spacious Historic Home in the Berkshires!
House (5 Bedrooms) | Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Guests can enjoy the cabin's expansive deck with seating and large windows offering a view of the surrounding forest.

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Relax in a serene garden setting surrounded by mature trees and lush greenery, with a stone fire pit and Adirondack chairs.

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
House (2 Bedrooms) | Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
2.0 out of 10, (1)
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Whitney by Avantstay Private Berkshires Estate
Stunning two-story house with a central entrance and beautifully manicured lawns.

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Skiing & Hiking: Water-view Home in the Berkshires
House (3 Bedrooms) | Interior

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Stunning two-story building with a central entrance and flanked windows, set amidst a beautifully manicured lawn.

Ashley Falls Home w/ Fire Pit: Hike & Ski!

3.0 star property
8.0 out of 10, Very good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cottage (1 Bedroom) | Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Lakefront Otis Home w/ Stunning Views & Boats!
House (2 Bedrooms) | Interior

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Stockbridge Home: Walk to Town Beach!
House (3 Bedrooms) | Interior

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Picturesque Cottage With Sunroom on Ashmere Lake!
Relax on the spacious deck with unobstructed lake views and enjoy the tranquil surroundings.

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Cozy Becket Cottage Escape w/ Lake Access!
Cottage (2 Bedrooms) | Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Massachusetts Vacation Rental w/ Deck & Grill
Interior

Massachusetts Vacation Rental w/ Deck & Grill

3.0 star property
Massachusetts Vacation Rental w/ Deck & Grill
Stockbridge Retreat w/ Pool & Hot Tub!
House (4 Bedrooms) | Interior

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Cottage (4 Bedrooms) | Front of property

1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge

3.0 star property
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Woodland Zen by Avantstay Modern Design + Patio
House (3 Bedrooms) | Front of property

Woodland Zen by Avantstay Modern Design + Patio

3.0 star property
Woodland Zen by Avantstay Modern Design + Patio
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
Relax on the deck with a barbecue grill and comfortable seating for two.

4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!

3.0 star property
4 Mi to Skiing: Cottage w/ Fire Pit in Richmond!
7 Mi to Catamount & Butternut: Mountain-view Home
House (3 Bedrooms) | Interior

7 Mi to Catamount & Butternut: Mountain-view Home

3.0 star property
7 Mi to Catamount & Butternut: Mountain-view Home
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top The Berkshires Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

10/10 Excellent
"A very clean and friendly environment. Staff were efficient and knowledgeable. Would appreciate two more handcap parking spaces at front of hotel. Thank you."
Susan 1-night trip
Posted 3 days ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Frequently asked questions

How much do cottages in The Berkshires cost?
Prices for cottages in The Berkshires range between and per night. Whatever your budget, you'll find an ideal place to get in touch with nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many cottages are there in The Berkshires?
Explore our 58 cottages in The Berkshires and then select your favourite. Whether you're organising a holiday with the whole fam or a break with pals, your perfect stay is just a few clicks away with Expedia.
Why book your cottage in The Berkshires with Expedia?
Booking a cottage in The Berkshires is as easy as clicking on your travel dates and choosing an ideal place for outdoor fun and relaxation. From upmarket retreats to affordable stays and cottages that include perks like a hot tub, Expedia has something for all styles and tastes. As for the best deals around? We've got them too!