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
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Popular amenities for Western Massachusetts rentals with a pool
House rentals with a pool
Home in Woodstock
4.98 out of 5 average rating, 100 reviewsWoodstock Historic Artist Estate- The Museum House
25 Jan – 1 Feb
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
13–20 Mar
Home in New Paltz
4.98 out of 5 average rating, 436 reviewsmidcentury modern in ground pool walk 2 trail/town
14–21 Jul
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
22–29 Oct
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
19–26 Nov
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
13–20 Sep
Home in Saugerties
5.0 out of 5 average rating, 132 reviewsUpstate Modern Scandinavian Barn in the Catskills
29 Dec – 5 Jan
Home in Deerfield
4.82 out of 5 average rating, 186 reviewsPerfectly Polished Deerfield Home 5 min to I-91
2–9 Oct
Apartment rentals with a pool
Apartment in Windham
4.89 out of 5 average rating, 133 reviewsCozy Mountain hideaway Windham, Hunter
21–28 Aug
Apartment in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
22–29 Sep
Apartment in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
23–30 Jun
Apartment in Norwich
4.88 out of 5 average rating, 211 reviewsThe N-V ...The Spa at the Norwich Inn.
30 Oct – 6 Nov
Apartment in Norwich
4.99 out of 5 average rating, 101 reviewsJacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan
12–19 Dec
Apartment in Norwich
4.99 out of 5 average rating, 112 reviewsPeaceful Oasis steps from Mohegan Sun
30 Oct – 6 Nov
Apartment in Norwich
4.99 out of 5 average rating, 167 reviewsModern & Cozy Villa with low cleaning charge!
26 Nov – 3 Dec
Apartment in Norwich
4.9 out of 5 average rating, 146 reviewsRenovated Condo rental at Norwich inn villa & Spa
16–23 Dec
Home rentals with a private pool
Home in Lagrangeville
4.84 out of 5 average rating, 120 reviewsClassic Hudson Valley Farmhouse Nestled in 9 Rolling Acres
27 Sep – 4 Oct
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
17–24 Sep
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
12–19 Mar
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
31 Aug – 7 Sep
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
13–20 Sep
Destinations to explore
- Cambridge Holiday rentals
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- Providence Holiday rentals
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- Jersey City Holiday rentals
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