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
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Home in New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Litchfield
4.93 out of 5 average rating, 165 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in Deerfield
4.81 out of 5 average rating, 187 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
Apartment rentals with a pool
Apartment in Windham
4.89 out of 5 average rating, 134 reviewsCozy Mountain hideaway Windham, Hunter
Apartment in Norwich
4.88 out of 5 average rating, 211 reviewsThe N-V ...The Spa at the Norwich Inn.
Apartment in Norwich
4.99 out of 5 average rating, 115 reviewsPeaceful Oasis steps from Mohegan Sun
Apartment in Norwich
4.9 out of 5 average rating, 147 reviewsRenovated Condo rental at Norwich inn villa & Spa
Apartment in Norwich
4.99 out of 5 average rating, 101 reviewsJacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan
Apartment in Norwich
4.99 out of 5 average rating, 168 reviewsModern & Cozy Villa with low cleaning charge!
Apartment in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Apartment in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 121 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
Home in Kerhonkson
4.94 out of 5 average rating, 326 reviewsCountry House: Rustic Charm With Modern Feel
Villa in Coxsackie
4.99 out of 5 average rating, 80 reviewsMagnificent Hudson River Estate with Infinity Pool and Spa
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Destinations to explore
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