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
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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, 308 reviewsCharming cottage w/ gorgeous views.
Guest favorite
Home in New Lebanon
4.99 out of 5 average rating, 350 reviewsThe old sawmill from 1771
Guest favorite
Home in Lee
5.0 out of 5 average rating, 235 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Guest favorite
Home in Chester
4.96 out of 5 average rating, 313 reviewsRiverfront Getaway
Guest favorite
Home in Canaan
5.0 out of 5 average rating, 136 reviewsCountry Cottage
Guest favorite
Home in Kingston
4.96 out of 5 average rating, 280 reviewsThis New House
Guest favorite
Home in Germantown
4.96 out of 5 average rating, 260 reviewsModern Cottage, Views, Walking Trails, Fireplace!
Guest favorite
Home in Cornwall
4.92 out of 5 average rating, 231 reviewsSecluded modern forest cabin with private brook
Other great vacation rentals in The Berkshires
Guest favorite
Loft in East Nassau
4.99 out of 5 average rating, 154 reviewsDog Friendly Farm Spring bird watching
Guest favorite
Cabin in North Adams
4.95 out of 5 average rating, 183 reviewsMahican Cabin - A Private Nature's Reserve For 2
Guest favorite
Cottage in Kinderhook
4.98 out of 5 average rating, 176 reviewsThe Cottage on Sylvester Street
Guest favorite
Apartment in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Guest favorite
Earthen home in West Sand Lake
4.98 out of 5 average rating, 152 reviewsThe Hobbit House at June Farms
Guest favorite
Guest suite in Canaan
4.98 out of 5 average rating, 297 reviewsWalk to Brewery in Historic Railroad Depot
Guest favorite
Tiny home in Wilmington
4.99 out of 5 average rating, 148 reviewsBeautiful Timber Frame Retreat
Guest favorite
Tiny home in Chatham
4.99 out of 5 average rating, 154 reviewsBLUSH: Boutique TINY home*private spa*walk to town
Destinations to explore
- Rentals with a fire pit The Berkshires
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