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
Get the amount of space that is right for you
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, 348 reviewsThe old sawmill from 1771
7–14 Sep
€ 146 per night
Guest favourite
Cottage in Petersham
4.99 out of 5 average rating, 150 reviewsCider House Cottage
4–11 Jan
€ 153 per night
Guest favourite
Tiny home in New Paltz
4.99 out of 5 average rating, 743 reviewsHudson Valley Tiny House
13–20 Jul
€ 115 per night
Guest favourite
Home in Monterey
4.93 out of 5 average rating, 307 reviewsCharming cottage w/ gorgeous views.
21–28 Nov
€ 180 per night
Guest favourite
Flat in Sheffield
5.0 out of 5 average rating, 319 reviewsHideaway with Spectacular Berkshire Views
13–20 Dec
€ 184 per night
Guest favourite
Yurt in Pattersonville
4.99 out of 5 average rating, 778 reviewsMariaville Goat Farm Yurt
29 Oct – 5 Nov
€ 148 per night
Guest favourite
Earthen home in West Sand Lake
4.98 out of 5 average rating, 150 reviewsThe Hobbit House at June Farms
25 Mar – 1 Apr
€ 372 per night
Guest favourite
Barn in Marlboro
4.95 out of 5 average rating, 263 reviewsThe Studio With a View. Bring your dog, too!
13–20 Nov
€ 158 per night
Destinations to explore
- Rentals with lake access The Berkshires
- Lakehouse rentals The Berkshires
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- Rentals with a washing machine and dryer The Berkshires
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