Vacation rentals with a pool in Berkshire County
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Berkshire County
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.
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Vacation rentals for every style
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Popular amenities for Berkshire County rentals with a pool
House rentals with a pool
Guest favorite
Home in Otis
4.91 out of 5 average rating, 11 reviewsBerkshires Oasis Retreat: Art Meets Nature
Guest favorite
Home in Pittsfield
4.94 out of 5 average rating, 17 reviewsBerkshire Lakeside Retreat
Guest favorite
Home in East Chatham
5 out of 5 average rating, 5 reviewsRed Rock Summit: Mtn Escape w/ Pool, Pond + Views
Guest favorite
Home in Lee
4.99 out of 5 average rating, 76 reviewsBerkshire Vacation Home in Lee
Guest favorite
Home in Hillsdale
4.89 out of 5 average rating, 27 reviewsHilltop: Panoramic Views w/ Pool near Catamount
Superhost
Home in Cheshire
4.93 out of 5 average rating, 70 reviewsBerkshire County modern home + pool
Superhost
Home in Dalton
4.88 out of 5 average rating, 92 reviewsPrivate & Stylish Berkshires House for All Seasons
Guest favorite
Home in Great Barrington
4.98 out of 5 average rating, 41 reviewsSix-bedroom country house with pool and hot tub
Condo rentals with a pool
Superhost
Condo in Hancock
5 out of 5 average rating, 6 reviewsCondo Resort at Jiminy Peak Ski Mountain's Base
Guest favorite
Condo in Hancock
4.98 out of 5 average rating, 42 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Condo in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Condo in Hancock
4.62 out of 5 average rating, 143 reviewsJiminy Peak Country Inn 1 Bedroom Suite
Condo in Hancock
4.8 out of 5 average rating, 5 reviewsSki-in/Ski-Out on Jiminy Peak
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