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Featured Cottages in The Berkshires

A-frame Cabin w/ Furnished Deck in Becket!
Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Luxury Vacation Rental in the Berkshires!
Interior

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Front of property

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

3.0 star property
10.0 out of 10, Exceptional, (1)
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Skiing & Hiking: Water-view Home in the Berkshires
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Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Spacious Historic Home in the Berkshires!
Interior

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
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Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Interior

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!
Lakefront Otis Home w/ Stunning Views & Boats!
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Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Cozy Stockbridge Cabin - Walk to Beach & Lake!
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
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Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
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Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Stockbridge Home: Walk to Town Beach!
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Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Picturesque Cottage With Sunroom on Ashmere Lake!
Interior

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!
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Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
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Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
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!
Interior

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
Renovated Lakefront House w/ Dock: Pets Welcome!
Interior

Renovated Lakefront House w/ Dock: Pets Welcome!

3.0 star property
Renovated Lakefront House w/ Dock: Pets Welcome!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Interior

Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns

3.0 star property
10.0 out of 10, Exceptional, (1)
"We had an amazing experience! Such a beautiful home and amazing host! We loved it! Definitely staying here again. Highly recommend! Thank you! "
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
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

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"It's just a nice place and the staff is very nice "
Robin 5-night trip
Posted 3 days ago
The Yankee, Trademark Collection by Wyndham

Find out more about The Berkshires

Find out more about The Berkshires

The Berkshires Cottages information

Number of reviews
3
Accommodation
58 Cottages
Lowest Price
Highest Price

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 favorite. Whether you're organizing a vacation 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!

Explore a world of travel with Expedia

Explore a world of travel with Expedia