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, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Nov 6 – 13
Home in Saugerties
4.96 out of 5 average rating, 150 reviewsLux 1800's renovated farmhouse w/hot tub+pool
Oct 21 – 28
Home in Cottekill
4.95 out of 5 average rating, 242 reviewsPeace & Privacy - High Falls (hot tub & salt pool)
Jul 22 – 29
Home in Woodstock
4.91 out of 5 average rating, 192 reviewsGlenford Studio with Pool & Mountain Views
Jul 15 – 22
Home in Pittsfield
4.96 out of 5 average rating, 56 reviewsBerkshire Getaway Ranch 3 acres + saltwater pool
Oct 16 – 23
Home in Pittsfield
4.97 out of 5 average rating, 39 reviewsBerkshire Lakefront Home W/Pool-100%Renovated
Nov 22 – 29
Home in Pittsfield
5.0 out of 5 average rating, 41 reviewsStunning Berkshires Retreat, Large and Private
Sep 6 – 13
Home in Richmond
4.96 out of 5 average rating, 23 reviewsEscape to The Berkshires w/Pool by Evergreen Home
May 13 – 20
Condo rentals with a pool
Condo in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
Jun 24 – Jul 1
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Sep 17 – 24
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Summer Mountain Oasis: Base of Mount Snow Retreat
Jan 30 – Feb 6
Condo in Stratton
4.88 out of 5 average rating, 107 reviewsPerfect Location! Steps to Village and Mountain
Sep 13 – 20
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Oct 14 – 21
Condo in Hancock
4.9 out of 5 average rating, 51 reviewsJiminy Peak Country Inn - ski in/out condo MT view
Sep 22 – 29
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
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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