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
Home in Wilmington
4 bedroom Ski House 15 min to Mount Snow
Home in Wilmington
The Vermont Barn (Mount Snow)
Home in Chesterfield
High Field Farm
Home in Amherst
Calm Post+Beam Retreat
Home in Shelburne Falls
Beautiful home for a cozy family getaway! W/pool !
Home in Enfield
3 bdrm house great neighborhood
Home in Cheshire
Berkshire County modern home + pool
Home in Richmond
Escape to The Berkshires w/Pool by Evergreen Home
Condo rentals with a pool
Condo in Hancock
Upscale 2 bed/2bath Condo at a Mountain Resort!
Condo in Hancock
Jiminy Peak Country Inn - ski in/out condo MT view
Condo in Hancock
All-season Berkshires ski resort condo - Sitzmark
Condo in Hancock
Jiminy Peak Apartment
Condo in Hancock
Unique - Country suite @ Jiminy Peak
Condo in Hancock
Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base
Condo in Hancock
SKI-IN SKI-OUT LIFT&MT.VIEWS GR8 4SEASON LOC.Unit2
Condo in Wilmington
Crafts Inn in Vermont 1br suite, Saturday check-in
Destinations to explore
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- Rentals with pools United States
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