Vacation 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.
Vacation 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 Woodstock
4.98 out of 5 average rating, 101 reviewsWoodstock Historic Artist Estate- The Museum House
Home in Kerhonkson
4.89 out of 5 average rating, 141 reviewsScandinavian lux retreat, views & pool
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Home in Litchfield
4.93 out of 5 average rating, 166 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Home in Woodstock
4.91 out of 5 average rating, 213 reviewsJapanese Teahouse & Onsen, outside shower, tennis
Condo rentals with a pool
Condo in Windham
4.89 out of 5 average rating, 136 reviewsCozy Mountain hideaway Windham, Hunter
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Condo in Norwich
4.99 out of 5 average rating, 119 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
4.88 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, 103 reviewsJacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan
Condo in Norwich
4.99 out of 5 average rating, 170 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
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
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