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 Saugerties
5.0 out of 5 average rating, 133 reviewsUpstate Modern Scandinavian Barn in the Catskills
Home in Hudson
4.95 out of 5 average rating, 112 reviewsHudson Retreat w/HotTub, PlungePool+ OutdoorShower
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Home in Staatsburg
4.98 out of 5 average rating, 105 reviewsHilltop Escape ~ 25 acre private retreat
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Home in Pittsfield
4.96 out of 5 average rating, 56 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
Home in Richmond
4.96 out of 5 average rating, 23 reviewsEscape to The Berkshires w/Pool by Evergreen Home
Home in Pittsfield
4.98 out of 5 average rating, 40 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Condo rentals with a pool
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Summer Mountain Oasis: Base of Mount Snow Retreat
Condo in Dover
4.88 out of 5 average rating, 146 reviewsCozy condo with great views of Mt. Snow
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Condo in Hancock
4.95 out of 5 average rating, 19 reviewsUpscale 2 bed/2bath Condo at a Mountain Resort!
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, 22 reviewsJiminy Peak Apartment
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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