Vacation rentals with a pool in Pittsfield
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pittsfield
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 Pittsfield rentals with a pool
House rentals with a pool
Home in Rhinebeck
4.96 out of 5 average rating, 164 reviewsOn The Hill in Rhinebeck
Dec 20 – 27
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Dec 18 – 25
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Sep 16 – 23
Home in Catskill
4.93 out of 5 average rating, 164 reviewsThe Grandview | Catskill, NY
Sep 16 – 23
Home in Wilmington
4.9 out of 5 average rating, 131 reviews4 bedroom Ski House 15 min to Mount Snow
Jan 12 – 19
Home in Wilmington
4.88 out of 5 average rating, 150 reviewsAdams Farm-"The Little Farmhouse"
Jun 18 – 25
Home in Pittsfield
4.96 out of 5 average rating, 56 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
Oct 7 – 14
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Sep 26 – Oct 3
Condo rentals with a pool
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Sep 7 – 14
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Mountain Oasis: Base of Mount Snow Retreat*
Sep 22 – 29
Condo in Dover
4.88 out of 5 average rating, 146 reviewsCozy condo with great views of Mt. Snow
Oct 12 – 19
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Sep 29 – Oct 6
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Dec 9 – 16
Condo in Hancock
4.9 out of 5 average rating, 21 reviewsAll-season Berkshires ski resort condo - Sitzmark
Oct 8 – 15
Condo in Hancock
4.96 out of 5 average rating, 27 reviewsSKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
May 3 – 10
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
Oct 12 – 19
Quick stats about vacation rentals with a pool in Pittsfield
Total rentals
20 properties
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
10 properties are a good fit for families
Total number of reviews
670 reviews
Nightly prices starting at
$60 before taxes and fees
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