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 Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Home in Ghent
4.87 out of 5 average rating, 271 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Home in Litchfield
4.93 out of 5 average rating, 165 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 Deerfield
4.81 out of 5 average rating, 187 reviewsPerfectly Polished Deerfield Home 5 min to I-91
Home in Keene
4.93 out of 5 average rating, 183 reviewsThe Brick House on Washington Street
Home in Wilmington
4.9 out of 5 average rating, 132 reviews4 bedroom Ski House 15 min to Mount Snow
Home in Woodstock
4.93 out of 5 average rating, 210 reviewsCedar Ridge
Condo rentals with a pool
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
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.
Condo in Dover
4.99 out of 5 average rating, 105 reviews*Summer Mountain Oasis: Base of Mount Snow Retreat
Condo in Stratton
4.88 out of 5 average rating, 107 reviewsPerfect Location! Steps to Village and Mountain
Condo in Dover
4.87 out of 5 average rating, 222 reviewsMt Snow Ski In/Out at Seasons
Condo in Dover
4.96 out of 5 average rating, 23 reviewsSki in Ski out condo great location
Condo in Dover
5.0 out of 5 average rating, 36 reviewsFour Seasons Slope-side Getaway at Mount Snow
Destinations to explore
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