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 Dalton
4.88 out of 5 average rating, 113 reviewsThe Yellow House
Feb 14 – 21
Home in Lee
4.89 out of 5 average rating, 235 reviewsCozy Berkshires Cottage
Sep 13 – 20
Home in Kingston
4.97 out of 5 average rating, 276 reviewsThis New House
Dec 15 – 22
Home in New Paltz
4.97 out of 5 average rating, 677 reviewsVictorian Haven
Mar 8 – 15
Home in Germantown
4.95 out of 5 average rating, 362 reviewsScandinavian Barn Featured in Airbnb Magazine
Sep 27 – Oct 4
Home in Great Barrington
4.96 out of 5 average rating, 213 reviewsJaw dropping mountain & lake views
Jan 7 – 14
Home in Chester
4.96 out of 5 average rating, 311 reviewsRiverfront Getaway
Jul 28 – Aug 4
Other great vacation rentals in The Berkshires
Apartment in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
Dec 28 – Jan 4
Cottage in Great Barrington
4.98 out of 5 average rating, 126 reviewsNewly built cottage on working farm
Mar 10 – 17
Barn in Marlboro
4.95 out of 5 average rating, 263 reviewsThe Studio With a View. Bring your dog, too!
Aug 26 – Sep 2
Earthen home in West Sand Lake
4.98 out of 5 average rating, 150 reviewsThe Hobbit House at June Farms
Mar 25 – Apr 1
Yurt in Pattersonville
4.99 out of 5 average rating, 773 reviewsMariaville Goat Farm Yurt
Feb 28 – Mar 7
Apartment in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Jun 19 – 26
Loft in East Nassau
4.99 out of 5 average rating, 153 reviewsDog Friendly Farm Spring bird watching
Aug 29 – Sep 5
Tiny home in Wilmington
4.99 out of 5 average rating, 140 reviewsBeautiful Timber Frame Retreat
Aug 11 – 18
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