
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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Popular amenities for The Berkshires holiday rentals
Other great holiday rentals in The Berkshires
Top guest favourite

Chalet in Copake
4.98 out of 5 average rating, 66 reviewsPrivate upstate home nestled in the Hudson Valley
Top guest favourite

Tiny home in Chatham
5 out of 5 average rating, 23 reviewsRomantic-Private-Western Tiny Cabin + hot tub
Guest favourite

Home in Great Barrington
4.93 out of 5 average rating, 42 reviewsCozy. Clean. Free bagel shop.
Top guest favourite

Home in Egremont
5 out of 5 average rating, 41 reviewsThe Catamount Ski Haus with Pool & Hot Tub
Top guest favourite

Loft in Great Barrington
5 out of 5 average rating, 32 reviewsThe Nest 5 min walk to downtown Great Barrington
Top guest favourite

Guest house in Cornwall
5 out of 5 average rating, 53 reviewsThe Pool Cottage at Narrow Valley Estate
Top guest favourite

Home in East Jewett
4.97 out of 5 average rating, 62 reviewsCreekside Couple's Retreat w/Hot tub, Sauna & More
Top guest favourite

Cabin in Ancram
5 out of 5 average rating, 36 reviewsLuxury Eco Stay, Featured in The Guardian, Hemp
Destinations to explore
- Aparthotel rentals The Berkshires
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- Rentals with an accessible-height toilet The Berkshires
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- Guest house rentals The Berkshires
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