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 Athens
4.94 out of 5 average rating, 114 reviewsPrivate lakefront home, hot tub & resort amenities
Home in Catskill
4.97 out of 5 average rating, 37 reviewsHudson Valley & Catskill Mountain Views • Hot Tub
Home in Hillsdale
5 out of 5 average rating, 5 reviews*Majestic views*Hot tub*Firepit*Games*Sleeps 14
Home in Lee
4.99 out of 5 average rating, 77 reviewsBerkshire Vacation Home in Lee
Home in Cheshire
4.93 out of 5 average rating, 70 reviewsBerkshire County modern home + pool
Home in Dalton
4.88 out of 5 average rating, 92 reviewsPrivate & Stylish Berkshires House for All Seasons
Home in Hudson
5 out of 5 average rating, 32 reviewsHudson Saltbox
Home in Wilmington
4.83 out of 5 average rating, 162 reviewsThe Vermont Barn (Mount Snow)
Condo rentals with a pool
Condo in Hancock
5 out of 5 average rating, 6 reviewsCondo Resort at Jiminy Peak Ski Mountain's Base
Condo in Hancock
4.98 out of 5 average rating, 42 reviewsJiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Condo in Dover
4.87 out of 5 average rating, 228 reviewsMt Snow Ski In/Out at Seasons
Condo in Dover
4.99 out of 5 average rating, 105 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo in Dover
4.95 out of 5 average rating, 37 reviewsSki in Ski out condo great location
Condo in Dover
5 out of 5 average rating, 51 reviewsFour Seasons Slope-side Getaway at Mount Snow
Condo in Dover
4.87 out of 5 average rating, 99 reviews⛷ Walk to Mt. Snow-Spa-Pool-Fireplace ⛷
Condo in Dover
4.99 out of 5 average rating, 112 reviewsWinter Bliss: Cozy Stay near Mount Snow!
Quick stats about vacation rentals with a pool in Pittsfield
Total rentals
20 properties
Nightly prices starting at
$60 before taxes and fees
Total number of reviews
680 reviews
Family-friendly rentals
10 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
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