Holiday rentals with a pool in The Berkshires
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in The Berkshires
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
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Popular amenities for The Berkshires rentals with a pool
House rentals with a pool
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Home in Pound Ridge
5.0 out of 5 average rating, 126 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
Home in Cheshire
5.0 out of 5 average rating, 119 reviewsPool House
Home in Saugerties
5.0 out of 5 average rating, 133 reviewsUpstate Modern Scandinavian Barn in the Catskills
Home in Woodstock
4.91 out of 5 average rating, 214 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Home in Cottekill
4.96 out of 5 average rating, 245 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Apartment rentals with a pool
Apartment in Windham
4.89 out of 5 average rating, 136 reviewsCozy Mountain hideaway Windham, Hunter
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Apartment in Vernon Township
4.97 out of 5 average rating, 220 reviewsRustic Chic at Mountain Creek! Pool Open All Year!
Apartment in Vernon Township
4.97 out of 5 average rating, 146 reviewsComfy Studio at Mountain Creek Resort
Apartment in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Apartment in Norwich
4.99 out of 5 average rating, 119 reviewsPeaceful Oasis steps from Mohegan Sun
Apartment in Vernon Township
4.95 out of 5 average rating, 738 reviewsAppalachian Lodge Top Floor w/views
Apartment in Norwich
4.88 out of 5 average rating, 211 reviewsThe N-V ...The Spa at the Norwich Inn.
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 121 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Home in Kerhonkson
4.94 out of 5 average rating, 326 reviewsCountry House: Rustic Charm With Modern Feel
Farm stay in Fleischmanns
4.91 out of 5 average rating, 11 reviewsEscape to a Dreamy 1857 Farmhouse in Fleischmanns
Villa in Coxsackie
4.99 out of 5 average rating, 80 reviewsMagnificent Hudson River Estate with Infinity Pool and Spa
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
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