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
Get the amount of space that is right for you
Popular amenities for The Berkshires vacation rentals
The Berkshires house rentals
Home in Lee
4.9 out of 5 average rating, 209 reviews1817 Berkshire Farmhouse- Close to Everything.
Home in Monterey
4.93 out of 5 average rating, 310 reviewsCharming cottage w/ gorgeous views.
Home in Germantown
4.96 out of 5 average rating, 261 reviewsModern Cottage, Views, Walking Trails, Fireplace!
Home in Chester
4.96 out of 5 average rating, 316 reviewsRiverfront Getaway
Home in Catskill
4.99 out of 5 average rating, 137 reviewsAthens, NY House - 1 Bedroom "Want to Get Away"?
Home in Rhinebeck
5.0 out of 5 average rating, 165 reviewsEagle Rock House
Home in Catskill
4.96 out of 5 average rating, 138 reviewsHEAVEN ON EARTH - Hudson Riverfront Home
Home in Germantown
4.95 out of 5 average rating, 368 reviewsAirbnb Magazine Featured Gorgeous Swedish Barn
Other great vacation rentals in The Berkshires
Guesthouse in Williamstown
4.93 out of 5 average rating, 220 reviewsPerfect Base for Your Berkshire Adventure
Loft in East Nassau
4.99 out of 5 average rating, 155 reviewsDog Friendly Farm Spring bird watching
Loft in Great Barrington
4.99 out of 5 average rating, 298 reviewsThe Old Red Barn
Cottage in Highland
4.91 out of 5 average rating, 545 reviewsLittle Yellow Cottage New Paltz - Kitchen wash/dry
Apartment in Plainfield
4.95 out of 5 average rating, 241 reviewsSunny carriage house apartment
Cabin in North Adams
4.95 out of 5 average rating, 188 reviewsMahican Cabin - A Private Nature's Reserve For 2
Earthen home in West Sand Lake
4.98 out of 5 average rating, 156 reviewsThe Hobbit House at June Farms
Guest suite in Canaan
4.98 out of 5 average rating, 300 reviewsWalk to Brewery in Historic Railroad Depot
Destinations to explore
- Smoking-friendly rentals The Berkshires
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