Holiday houses in The Berkshires
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Top-rated holiday rentals in The Berkshires
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for The Berkshires holiday rentals
Other great holiday rentals in The Berkshires
Guest favourite
Home in New Lebanon
4.99 out of 5 average rating, 351 reviewsThe old sawmill from 1771
Guest favourite
Home in Monterey
4.93 out of 5 average rating, 311 reviewsCharming cottage w/ gorgeous views.
Guest favourite
Apartment in Sheffield
5.0 out of 5 average rating, 325 reviewsHideaway with Spectacular Berkshire Views
Guest favourite
Loft in East Nassau
4.99 out of 5 average rating, 156 reviewsDog Friendly Farm Spring bird watching
Guest favourite
Tiny home in Saugerties
4.94 out of 5 average rating, 226 reviewsGorgeous Tiny House with Mountain View
Guest favourite
Guesthouse in North Adams
5.0 out of 5 average rating, 214 reviewsNetherwood - North Adams Guest House with Views
Guest favourite
Loft in Great Barrington
4.99 out of 5 average rating, 299 reviewsThe Old Red Barn
Guest favourite
Cabin in Red Hook
4.96 out of 5 average rating, 311 reviewsModern Upstate Cabin, near Rhinebeck NY
Destinations to explore
- Fitness-friendly rentals The Berkshires
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