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Vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for The Berkshires rentals with a pool
House rentals with a pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-20903823/original/6471dd1a-df37-442b-b1f5-4e86de0d6c26.jpeg?im_w=720)
Home in Saugerties
5 out of 5 average rating, 136 reviewsUpstate Modern Scandinavian Barn in the Catskills
![](https://a0.muscache.com/im/pictures/miso/Hosting-48998622/original/88942ff7-4b89-4544-b0db-81c0128db957.jpeg?im_w=720)
Home in Woodstock
4.98 out of 5 average rating, 106 reviewsWoodstock Historic Artist Estate- The Museum House
![](https://a0.muscache.com/im/pictures/57788583/e3a3a3ab_original.jpg?im_w=720)
Home in Cheshire
5 out of 5 average rating, 120 reviewsPool House
![](https://a0.muscache.com/im/pictures/miso/Hosting-49275774/original/612c0e08-b64a-45a4-9fae-7b4eecf6d251.jpeg?im_w=720)
Home in Pound Ridge
5 out of 5 average rating, 132 reviewsPeaceful Light-Filled Guesthouse 1 Hour From NYC
![](https://a0.muscache.com/im/pictures/9ca06d68-c24b-4211-9971-f86379c34adb.jpg?im_w=720)
Home in Cottekill
4.95 out of 5 average rating, 248 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
![](https://a0.muscache.com/im/pictures/a7067854-a496-4890-9a27-b7e4f6841e40.jpg?im_w=720)
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
![](https://a0.muscache.com/im/pictures/caab9624-e63a-4ae8-a523-cc8d80d13a90.jpg?im_w=720)
Home in Cold Spring
4.95 out of 5 average rating, 153 reviewsCozy, Modern Retreat in the Woods of Cold Spring
![](https://a0.muscache.com/im/pictures/prohost-api/Hosting-51976755/original/0c4d4b40-14eb-4106-8dba-cf8ab9829e55.jpeg?im_w=720)
Home in Woodstock
4.91 out of 5 average rating, 221 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Condo rentals with a pool
![](https://a0.muscache.com/im/pictures/miso/Hosting-52519968/original/238a81c6-203c-4d6d-80ed-9946cd9e0936.jpeg?im_w=720)
Condo in Windham
4.89 out of 5 average rating, 140 reviewsCozy Mountain hideaway Windham, Hunter
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Condo in Hancock
4.83 out of 5 average rating, 132 reviewsCozy Condo @ Jiminy Peak
![](https://a0.muscache.com/im/pictures/8c5eb1ef-2e86-4a5e-a65e-cdb5574e2a3b.jpg?im_w=720)
Condo in Windham
4.74 out of 5 average rating, 244 reviewsSummer getaway w/Pool & Tennis Court
![](https://a0.muscache.com/im/pictures/837b70ac-32f2-4eba-ba33-5b306d65ee38.jpg?im_w=720)
Condo in Stratton
4.96 out of 5 average rating, 119 reviewsCozy condo within walking distance to the slopes.
![](https://a0.muscache.com/im/pictures/c1bc3e13-a306-4946-bca4-1174b0f3fa16.jpg?im_w=720)
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
![](https://a0.muscache.com/im/pictures/miso/Hosting-698613026473577595/original/f3a72692-e5d5-4df8-b1d9-f2f858835427.jpeg?im_w=720)
Condo in Stratton
4.96 out of 5 average rating, 102 reviewsPremier Stratton Village Location - Pool & Hot Tub
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Condo in Stratton
4.88 out of 5 average rating, 108 reviewsPerfect Location! Steps to Village and Mountain
![](https://a0.muscache.com/im/pictures/hosting/Hosting-U3RheVN1cHBseUxpc3Rpbmc6MzY2MzkxOTA%3D/original/50cfedf2-3dab-4b00-81fa-93ef15c35ba1.jpeg?im_w=720)
Condo in Dover
4.99 out of 5 average rating, 107 reviews*Summer Mountain Oasis: Base of Mount Snow
Home rentals with a private pool
Home in Kerhonkson
4.95 out of 5 average rating, 329 reviewsCountry House: Rustic Charm With Modern Feel
![](https://a0.muscache.com/im/pictures/88a1f010-a56c-4ae5-8b87-dc5f47800fa3.jpg?im_w=720)
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
![](https://a0.muscache.com/im/pictures/c04f42ee-045f-4d41-9692-79ab2629caf7.jpg?im_w=720)
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Home in Lanesville
4.75 out of 5 average rating, 206 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
![](https://a0.muscache.com/im/pictures/f9ce4574-1de5-42a8-9892-a93bdaa72d14.jpg?im_w=720)
Home in Rhinebeck
5 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
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