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.
Vacation rentals for every style
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Popular amenities for The Berkshires vacation rentals
The Berkshires house rentals
Home in Pownal
4.98 out of 5 average rating, 218 reviewsCozy Vermont mini-house
Home in Catskill
4.96 out of 5 average rating, 138 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Home in Germantown
4.96 out of 5 average rating, 262 reviewsModern Cottage, Views, Walking Trails, Fireplace!
Home in Chester
4.96 out of 5 average rating, 316 reviewsRiverfront Getaway
Home in Kingston
4.96 out of 5 average rating, 284 reviewsThis New House
Home in Great Barrington
4.96 out of 5 average rating, 219 reviewsJaw dropping mountain & lake views
Home in New Paltz
4.97 out of 5 average rating, 689 reviewsVictorian Haven
Home in Monterey
4.93 out of 5 average rating, 117 reviewsPerfect Berkshire getaway.Cozy cottage.Great wifi.
Other great vacation rentals in The Berkshires
Cottage in Great Barrington
4.91 out of 5 average rating, 229 reviewsCottage on Scenic Road
Tiny home in Chatham
4.99 out of 5 average rating, 162 reviewsBLUSH: Boutique TINY home*private spa*walk to town
Guesthouse in North Bennington
4.98 out of 5 average rating, 162 reviewsBirch House - lake, green trees + modern comforts
Guest suite in Bethlehem
4.99 out of 5 average rating, 213 reviewsBreezy Crest private & restful w/antique charm
Cottage in Highland
4.91 out of 5 average rating, 549 reviewsLittle Yellow Cottage New Paltz - Kitchen wash/dry
Barn in Marlboro
4.95 out of 5 average rating, 268 reviewsThe Studio With a View. Bring your dog, too!
Apartment in Sheffield
5.0 out of 5 average rating, 325 reviewsHideaway with Spectacular Berkshire Views
Tiny home in Wilmington
4.99 out of 5 average rating, 154 reviewsBeautiful Timber Frame Retreat
Destinations to explore
- Rentals with pools The Berkshires
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- Family travel hub Tips and inspiration
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