Accommodation 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
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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
Condo rentals with a pool
Condo in Windham
4.89 out of 5 average rating, 134 reviewsCozy Mountain hideaway Windham, Hunter
Condo in Norwich
4.88 out of 5 average rating, 211 reviewsThe N-V ...The Spa at the Norwich Inn.
Condo in Norwich
4.99 out of 5 average rating, 115 reviewsPeaceful Oasis steps from Mohegan Sun
Condo in Norwich
4.9 out of 5 average rating, 147 reviewsRenovated Condo rental at Norwich inn villa & Spa
Condo in Norwich
4.99 out of 5 average rating, 101 reviewsJacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan
Condo in Norwich
4.99 out of 5 average rating, 168 reviewsModern & Cozy Villa with low cleaning charge!
Condo in Dover
4.99 out of 5 average rating, 100 reviewsWinter Dream! The Handle Lodge at Snowtree Condos
Condo 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
- Cambridge Accommodation & holiday rentals
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