Holiday rentals 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 Monterey
4.93 out of 5 average rating, 308 reviewsCharming cottage w/ gorgeous views.
Guest favourite
Loft in East Nassau
4.99 out of 5 average rating, 154 reviewsDog Friendly Farm Spring bird watching
Guest favourite
Cottage in Kinderhook
4.98 out of 5 average rating, 175 reviewsThe Cottage on Sylvester Street
Guest favourite
Earthen home in West Sand Lake
4.98 out of 5 average rating, 150 reviewsThe Hobbit House at June Farms
Guest favourite
Home in New Lebanon
4.99 out of 5 average rating, 348 reviewsThe old sawmill from 1771
Guest favourite
Home in Lee
5.0 out of 5 average rating, 234 reviewsBerkshire Mountain retreat with Urban eco-luxuries
Guest favourite
Tiny home in Wilmington
4.99 out of 5 average rating, 144 reviewsBeautiful Timber Frame Retreat
Guest favourite
Flat in Lenox
4.88 out of 5 average rating, 170 reviewsStation House 1E Private Room & Bath
Destinations to explore
- Cabin rentals The Berkshires
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- Chalet rentals The Berkshires
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