
Holiday rentals with a pool in Western Massachusetts
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Western Massachusetts
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Western Massachusetts rentals with a pool
House rentals with a pool

Courtyard Garden | Pool | BBQ+Fire Tbl | Fireplace

Cedar Ridge: House or House+Apartment

Hudson Valley & Catskill Mountain Views • Hot Tub

High Field Farm

Upstate Modern Scandinavian Barn in the Catskills

Stunning Views, Bucolic Bliss in 1790s Farmhouse

Hilltop: Panoramic Views w/ Pool near Catamount

Berkshire County modern home + pool
Apartment rentals with a pool

Mount Snow Ski Chalet

Seasons on Mt Snow Condo - Ski/Hike/Bike/Swim

Mt Snow Ski In/Out at Seasons

Summer Dream! The Handle Lodge at Snowtree Condos

Cozy condo within walking distance to the slopes.

Walk to Mt. Snow-Spa-Summer Pool

Jiminy Peak Country Inn - ski in/out condo MT view

The Alpine Escape | Slope-Side Condo at Mount Snow
Destinations to explore
- Hudson Valley Holiday rentals
- Boston Holiday rentals
- The Hamptons Holiday rentals
- Long Island Holiday rentals
- Plainview Holiday rentals
- East River Holiday rentals
- New York Holiday rentals
- Pocono Mountains Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- Montreal Holiday rentals
- South Jersey Holiday rentals
- Cottage rentals Western Massachusetts
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- Beachfront rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Rentals with a firepit Western Massachusetts
- Rentals with beach access Western Massachusetts
- Hotel rentals Western Massachusetts
- Flat rentals Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Rentals with a patio Western Massachusetts
- Private suite rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a cinema Western Massachusetts
- Apartment rentals Western Massachusetts
- Rentals with a hot tub Western Massachusetts
- Tiny house rentals Western Massachusetts
- Lakehouse rentals Western Massachusetts
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- Rentals with a washing machine and dryer Western Massachusetts
- Chalet rentals Western Massachusetts
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- Guest house rentals Western Massachusetts
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- Waterfront rentals Western Massachusetts
- House rentals Western Massachusetts
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- Rentals with a kayak Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Farm stay rentals Western Massachusetts
- Rentals with an accessible-height toilet Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Rentals with lake access Western Massachusetts
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- Six Flags New England
- Taconic State Park
- Bushnell Park
- Berkshire East Mountain Resort
- Albany Center Gallery
- Jiminy Peak Mountain Resort
- Bash Bish Falls State Park
- Mount Greylock Ski Club
- Kent Falls State Park
- Norman Rockwell Museum
- Brimfield State Forest
- Catamount Mountain Ski Resort
- Mount Snow Ski Resort
- Dinosaur State Park
- Mohawk Mountain Ski Area
- Beartown State Forest
- Talcott Mountain State Park
- Wintonbury Hills Golf Course
- Hartford Golf Club
- Mount Sugarloaf State Reservation
- Bousquet Mountain Ski Area
- Bigelow Hollow State Park
- Bright Nights at Forest Park
- Hancock Shaker Village