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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Berkshire County rentals with a pool
House rentals with a pool
Home in Pittsfield
4.96 out of 5 average rating, 56 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Home in Hancock
5.0 out of 5 average rating, 5 reviewsBougie B's Mountainside Getaway
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 Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Home in Dalton
4.89 out of 5 average rating, 81 reviewsPrivate & Stylish Berkshires House for All Seasons
Condo rentals with a pool
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Condo in Hancock
4.93 out of 5 average rating, 15 reviewsLarge one bedroom, two full bath, full kitchen
Condo in Hancock
4.93 out of 5 average rating, 58 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit1
Condo in Hancock
4.97 out of 5 average rating, 37 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 New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
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