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 West Stockbridge
4.97 out of 5 average rating, 59 reviewsPanoramic Views, Indoor Pool by Evergreen Home
Nov 15 – 22
Home in Dalton
4.89 out of 5 average rating, 81 reviewsPrivate & Stylish Berkshires House for All Seasons
Jan 13 – 20
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Nov 7 – 14
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Nov 21 – 28
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Nov 29 – Dec 6
Home in West Stockbridge
5.0 out of 5 average rating, 6 reviewsPool is open Memorial Day Weekend! - Sleeps 13!
Oct 7 – 14
Home in Great Barrington
5.0 out of 5 average rating, 35 reviewsSix-bedroom country house with pool and hot tub
Sep 27 – Oct 4
Home in Pittsfield
4.97 out of 5 average rating, 39 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Apr 26 – May 3
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 23 – 30
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Dec 4 – 11
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Jul 27 – Aug 3
Condo in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
May 10 – 17
Condo in Hancock
4.93 out of 5 average rating, 15 reviewsLarge one bedroom, two full bath, full kitchen
Jul 11 – 18
Condo in Hancock
4.97 out of 5 average rating, 37 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Jan 12 – 19
Condo in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Mar 12 – 19
Condo in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
Nov 4 – 11
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