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, 308 reviewsCharming cottage w/ gorgeous views.
Guest favorite
Home in Lee
5.0 out of 5 average rating, 234 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Guest favorite
Home in New Lebanon
4.99 out of 5 average rating, 350 reviewsThe old sawmill from 1771
Guest favorite
Home in New Paltz
4.97 out of 5 average rating, 681 reviewsVictorian Haven
Guest favorite
Home in Canaan
5.0 out of 5 average rating, 136 reviewsCountry Cottage
Guest favorite
Home in Chester
4.96 out of 5 average rating, 312 reviewsRiverfront Getaway
Guest favorite
Home in Rhinebeck
5.0 out of 5 average rating, 165 reviewsEagle Rock House
Guest favorite
Home in Germantown
4.95 out of 5 average rating, 364 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Other great vacation rentals in The Berkshires
Guest favorite
Guesthouse in Stockbridge
4.96 out of 5 average rating, 178 reviewsModern studio with views of the treetops
Guest favorite
Tiny home in Chatham
4.99 out of 5 average rating, 186 reviewsTiny House on 70 Private Acres in Hudson Valley
Guest favorite
Guesthouse in Becket
4.93 out of 5 average rating, 258 reviewsCountry Cabin
Guest favorite
Apartment in Sheffield
5.0 out of 5 average rating, 322 reviewsHideaway with Spectacular Berkshire Views
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
Cabin in Copake Lake
4.94 out of 5 average rating, 181 reviewsSecluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS
Guest favorite
Guesthouse in Williamstown
4.97 out of 5 average rating, 148 reviewsBrookside Cottage
Guest favorite
Apartment in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Destinations to explore
- Lakehouse rentals The Berkshires
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- Monthly Rentals The Berkshires
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- Family travel hub Tips and inspiration
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