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
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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
Sep 14 – 21
Home in Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Jun 9 – 16
Home in New Marlborough
4.95 out of 5 average rating, 21 reviewsBerkshires Colonial Farmhouse
Dec 11 – 18
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Apr 14 – 21
Home in Pittsfield
4.97 out of 5 average rating, 38 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Oct 27 – Nov 3
Home in Dalton
4.89 out of 5 average rating, 80 reviewsPrivate & Stylish Berkshires House for All Seasons
Jun 10 – 17
Home in West Stockbridge
5.0 out of 5 average rating, 6 reviewsBella Vista with Pool, Screen Porch & Fire Pit
Nov 5 – 12
Home in Great Barrington
5.0 out of 5 average rating, 35 reviewsSix-bedroom country house with pool and hot tub
Apr 1 – 8
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
Sep 15 – 22
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Oct 15 – 22
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Aug 24 – 31
Condo in Hancock
4.95 out of 5 average rating, 21 reviewsJiminy Peak Apartment
May 9 – 16
Condo in Hancock
4.97 out of 5 average rating, 37 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Jan 4 – 11
Condo in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
Oct 30 – Nov 6
Condo in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Mar 4 – 11
Condo in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
Nov 7 – 14
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