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 Sheffield
4.94 out of 5 average rating, 16 reviewsPrivate Berkshire County Retreat
Jun 14 – 21
Home in Cheshire
4.94 out of 5 average rating, 50 reviewsBerkshire County modern home + pool
Nov 14 – 21
Home in Great Barrington
4.97 out of 5 average rating, 34 reviewsNewly Remodeled Private Estate-Pool, Tennis Court!
Dec 1 – 8
Home in Dalton
4.89 out of 5 average rating, 81 reviewsPrivate & Stylish Berkshires House for All Seasons
Mar 4 – 11
Home in Lee
4.98 out of 5 average rating, 62 reviewsBerkshire Vacation Home in Lee (Pool Opens in May)
Oct 17 – 24
Home in Great Barrington
5.0 out of 5 average rating, 52 reviewsStunning luxury home with pool
Nov 7 – 14
Home in New Marlborough
4.95 out of 5 average rating, 21 reviewsBerkshires Colonial Farmhouse
Nov 12 – 19
Home in Pittsfield
4.97 out of 5 average rating, 39 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Nov 1 – 8
Condo rentals with a pool
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Dec 1 – 8
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Aug 4 – 11
Condo in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
May 8 – 15
Condo in Hancock
4.95 out of 5 average rating, 22 reviewsJiminy Peak Apartment
Aug 10 – 17
Condo in Hancock
4.97 out of 5 average rating, 37 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Jan 9 – 16
Condo in Hancock
4.88 out of 5 average rating, 33 reviewsUnique - Country suite @ Jiminy Peak
Mar 9 – 16
Condo in New Ashford
Wyndham Bentley Brook - 2 BR Deluxe - Sleeps 8
Jan 2 – 9
Condo in Hancock
4.62 out of 5 average rating, 138 reviewsJiminy Peak Country Inn 1 Bedroom Suite
Aug 10 – 17
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