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 New Paltz
4.98 out of 5 average rating, 437 reviewsmidcentury modern in ground pool walk 2 trail/town
Jul 14 – 21
Home in Colrain
4.88 out of 5 average rating, 112 reviewsThe 1770 House
Mar 14 – 21
Home in Stormville
4.94 out of 5 average rating, 156 reviewsPrivate Hudson Valley Country Retreat
Dec 27 – Jan 3
Home in Ghent
4.87 out of 5 average rating, 270 reviewsModern Barn on 12 acres w Sauna, FirePit+swimming
Dec 17 – 24
Home in Hudson
4.93 out of 5 average rating, 227 reviewsCasa Luna Country Retreat with Pool, Hudson, NY
Sep 13 – 20
Home in Cheshire
5.0 out of 5 average rating, 118 reviewsPool House
Nov 16 – 23
Home in Litchfield
4.93 out of 5 average rating, 163 reviewsStunning Views, Bucolic Bliss in 1790s Farmhouse
Sep 12 – 19
Home in Cold Spring
4.95 out of 5 average rating, 152 reviewsCozy, Modern Retreat in the Woods of Cold Spring
Dec 14 – 21
Condo rentals with a pool
Condo in Windham
4.89 out of 5 average rating, 133 reviewsCozy Mountain hideaway Windham, Hunter
Aug 21 – 28
Condo in Hancock
4.83 out of 5 average rating, 131 reviewsCozy Condo @ Jiminy Peak
Apr 7 – 14
Condo in Norwich
4.99 out of 5 average rating, 112 reviewsPeaceful Oasis steps from Mohegan Sun
Oct 6 – 13
Condo in Stratton
4.96 out of 5 average rating, 118 reviewsCozy condo within walking distance to the slopes.
Jun 24 – Jul 1
Condo in Norwich
4.88 out of 5 average rating, 211 reviewsThe N-V ...The Spa at the Norwich Inn.
Nov 17 – 24
Condo in Norwich
4.99 out of 5 average rating, 101 reviewsJacuzzi/Sauna/Pool, On-site Spa, 3-mins to Mohegan
Dec 12 – 19
Condo in Norwich
4.99 out of 5 average rating, 167 reviewsModern & Cozy Villa with low cleaning charge!
Mar 30 – Apr 6
Condo in Norwich
4.9 out of 5 average rating, 146 reviewsRenovated Condo rental at Norwich inn villa & Spa
Nov 25 – Dec 2
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
Sep 27 – Oct 4
Home in Kerhonkson
4.94 out of 5 average rating, 325 reviewsCountry House: Rustic Charm With Modern Feel
Sep 17 – 24
Villa in Coxsackie
4.99 out of 5 average rating, 80 reviewsMagnificent Hudson River Estate with Infinity Pool and Spa
Apr 18 – 25
Home in Woodstock
4.6 out of 5 average rating, 10 reviewsLuxury Retreat in the Catskills
Sep 1 – 8
Home in Lanesville
4.77 out of 5 average rating, 205 reviewsGo Hiking and Skiing from a Family-Friendly Farmhouse
Mar 13 – 20
Home in Rhinebeck
5.0 out of 5 average rating, 65 reviewsRhinebeck Country Living with a Modern Twist
Oct 2 – 9
Destinations to explore
- Cambridge Vacation rentals
- New Haven Vacation rentals
- Lake George Vacation rentals
- Providence Vacation rentals
- Catskill Vacation rentals
- Albany Vacation rentals
- Philadelphia Vacation rentals
- Jersey City Vacation rentals
- New York Vacation rentals
- The Hamptons Vacation rentals
- Boston Vacation rentals
- Montreal Vacation rentals
- Rentals with pools United States
- Rentals with pools Boston
- Rentals with pools New York
- Rentals with pools New Hampshire
- Rentals with pools Massachusetts
- Rentals with a hot tub Western Massachusetts
- Family-friendly rentals Western Massachusetts
- Rentals with outdoor seating Western Massachusetts
- Ski-in/ski-out rentals Western Massachusetts
- Townhouse rentals Western Massachusetts
- Rentals with a fire pit Western Massachusetts
- Cottage rentals Western Massachusetts
- Cabin rentals Western Massachusetts
- Fitness-friendly rentals Western Massachusetts
- Bed and breakfasts Western Massachusetts
- Vacation home rentals Western Massachusetts
- Private suite rentals Western Massachusetts
- Pet-friendly rentals Western Massachusetts
- Rentals with breakfast Western Massachusetts
- Boutique hotel rentals Western Massachusetts
- Condo rentals Western Massachusetts
- Chalet rentals Western Massachusetts
- Rentals with an EV charger Western Massachusetts
- Farmstay rentals Western Massachusetts
- Rentals with a washer and dryer Western Massachusetts
- Wheelchair accessible rentals Western Massachusetts
- Smoking-friendly rentals Western Massachusetts
- Rentals with a home theater Western Massachusetts
- House rentals Western Massachusetts
- Rentals with a patio Western Massachusetts
- Rentals with a fireplace Western Massachusetts
- Rentals with a sauna Western Massachusetts
- Monthly Rentals Western Massachusetts
- Apartment rentals Western Massachusetts
- Rentals with a kayak Western Massachusetts
- Rentals with lake access Western Massachusetts
- Beachfront rentals Western Massachusetts
- Lakehouse rentals Western Massachusetts
- Waterfront rentals Western Massachusetts
- Hotel rentals Western Massachusetts
- Rentals with an accessible height toilet Western Massachusetts
- Rentals with beach access Western Massachusetts
- Kid-friendly rentals Western Massachusetts
- Guesthouse rentals Western Massachusetts
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom