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.
Vacation rentals for every style
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Popular amenities for The Berkshires vacation rentals
Other great vacation rentals in The Berkshires
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
Feb 6 – 13
Home in Lee
4.89 out of 5 average rating, 235 reviewsCozy Berkshires Cottage
Sep 22 – 29
Home in Kingston
4.97 out of 5 average rating, 276 reviewsThis New House
Jan 13 – 20
Home in New Paltz
4.97 out of 5 average rating, 677 reviewsVictorian Haven
Jan 21 – 28
Home in Germantown
4.95 out of 5 average rating, 362 reviewsScandinavian Barn Featured in Airbnb Magazine
Aug 24 – 31
Home in Canaan
5.0 out of 5 average rating, 134 reviewsCountry Cottage
Feb 27 – Mar 6
Home in Chester
4.96 out of 5 average rating, 310 reviewsRiverfront Getaway
Jul 28 – Aug 4
Home in Pownal
4.99 out of 5 average rating, 212 reviewsCozy Vermont mini-house
Oct 27 – Nov 3
Other great vacation rentals in The Berkshires
Tiny home in Wilmington
4.99 out of 5 average rating, 140 reviewsBeautiful Timber Frame Retreat
Sep 30 – Oct 7
Apartment in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
Dec 27 – Jan 3
Cottage in Petersham
4.99 out of 5 average rating, 149 reviewsCider House Cottage
Jun 10 – 17
Cottage in Great Barrington
4.98 out of 5 average rating, 126 reviewsNewly built cottage on working farm
Mar 8 – 15
Guesthouse in Stockbridge
4.96 out of 5 average rating, 175 reviewsModern studio with views of the treetops
Sep 12 – 19
Earthen home in West Sand Lake
4.98 out of 5 average rating, 150 reviewsThe Hobbit House at June Farms
Apr 12 – 19
Barn in Marlboro
4.95 out of 5 average rating, 263 reviewsThe Studio With a View. Bring your dog, too!
Aug 26 – Sep 2
Yurt in Pattersonville
4.99 out of 5 average rating, 773 reviewsMariaville Goat Farm Yurt
Nov 23 – 30
Destinations to explore
- Rentals with lake access The Berkshires
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