
Vacation rentals with a pool in Pioneer Valley
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Pioneer Valley
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 Pioneer Valley rentals with a pool
House rentals with a pool

Stay in Robert Frost's beautiful house

Berkshires Oasis Retreat: Art Meets Nature

Happy Valley getaway

Ezekiel's Palace 24th

Sweet cape near U Mass

Luxury Home * Pool * Fireplace

Enjoy some time feeling the comforts of home!

High Field Farm
Other vacation rentals with a pool

Karin's Place: Phenomenal Safe Guest House w/pool

Rural retreat in Colebrook CT

Modern Escape in the Woods of the Berkshires - 4br

Family Winter Retreat w/ Hot Tub: 14 Mi to Slopes!

Vintage BARN Apt-POOL-HotTub-FirePit-Farms-Foliage

Entire Berkshires 1830s Home filled with antiques

11-acre mid-century private estate, pool

Beautiful 2BD Villa in Berkshires Resort
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- Rentals with pools Massachusetts
- Rentals with pools United States
- Six Flags New England
- Jiminy Peak Mountain Resort
- Monadnock State Park
- TPC River Highlands
- Berkshire East Mountain Resort
- Brownstone Adventure Sports Park
- Bash Bish Falls State Park
- Bushnell Park
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Norman Rockwell Museum
- Bigelow Hollow State Park
- Dinosaur State Park
- Wintonbury Hills Golf Course
- Mount Greylock Ski Club
- Taconic State Park
- Mount Tom State Reservation
- Mohawk Mountain Ski Area
- Beartown State Forest
- Mount Sugarloaf State Reservation
- The Shattuck Golf Club
- Hartford Golf Club
- Hancock Shaker Village
- Talcott Mountain State Park