Holiday 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.
Holiday rentals for every style
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Popular amenities for Berkshire County rentals with a pool
House rentals with a pool
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
Home in New Marlborough
4.95 out of 5 average rating, 21 reviewsBerkshires Colonial Farmhouse
Home in Pittsfield
4.98 out of 5 average rating, 40 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Home in West Stockbridge
5.0 out of 5 average rating, 18 reviewsBerkshire House on the Hill
Home in Great Barrington
5.0 out of 5 average rating, 35 reviewsSix-bedroom country house with pool and hot tub
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Home in West Stockbridge
5.0 out of 5 average rating, 6 reviewsHeated Pool, Screened Porch, Gardens, Sleeps 13!
Home in Pittsfield
4.96 out of 5 average rating, 56 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
Apartment rentals with a pool
Apartment in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Apartment in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Apartment in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Apartment in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
Apartment in Hancock
4.95 out of 5 average rating, 22 reviewsJiminy Peak Apartment
Apartment in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Apartment in Hancock
4.97 out of 5 average rating, 37 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Apartment in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
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