The Berkshires vacation rentals
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Top-rated vacation rentals in The Berkshires
Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires vacation rentals
Other great vacation rentals in The Berkshires
Guest favorite
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Guest favorite
Home in Lee
4.89 out of 5 average rating, 235 reviewsCozy Berkshires Cottage
Guest favorite
Home in Kingston
4.97 out of 5 average rating, 276 reviewsThis New House
Guest favorite
Home in New Paltz
4.97 out of 5 average rating, 677 reviewsVictorian Haven
Guest favorite
Home in Germantown
4.95 out of 5 average rating, 362 reviewsScandinavian Barn Featured in Airbnb Magazine
Guest favorite
Home in Canaan
5.0 out of 5 average rating, 134 reviewsCountry Cottage
Guest favorite
Home in Chester
4.96 out of 5 average rating, 310 reviewsRiverfront Getaway
Guest favorite
Home in Pownal
4.99 out of 5 average rating, 212 reviewsCozy Vermont mini-house
Other great vacation rentals in The Berkshires
Guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 140 reviewsBeautiful Timber Frame Retreat
Guest favorite
Apartment in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
Guest favorite
Cottage in Petersham
4.99 out of 5 average rating, 149 reviewsCider House Cottage
Guest favorite
Cottage in Great Barrington
4.98 out of 5 average rating, 126 reviewsNewly built cottage on working farm
Guest favorite
Guesthouse in Stockbridge
4.96 out of 5 average rating, 175 reviewsModern studio with views of the treetops
Guest favorite
Earthen home in West Sand Lake
4.98 out of 5 average rating, 150 reviewsThe Hobbit House at June Farms
Guest favorite
Barn in Marlboro
4.95 out of 5 average rating, 263 reviewsThe Studio With a View. Bring your dog, too!
Guest favorite
Yurt in Pattersonville
4.99 out of 5 average rating, 772 reviewsMariaville Goat Farm Yurt
Destinations to explore
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- Family travel hub Tips and inspiration
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