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.

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Guest favourite

Cottage in Averill Park

4.94 out of 5 average rating, 138 reviews

Cozy cottage with pool, walking distance to lake

Cozy cottage with pool, fire-pit, and a short walk to the lake. Enjoy a relaxing stay at our home exploring the lake and local eateries, or a fun family getaway at the pool. Just a short drive to your winter fun at Jiminy Peak for skiing, or Saratoga during track Season. Minutes to the Crooked Lake House for your wedding stays. Don't forget your four legged family members, while you're snowshoeing, or swimming at the lake. With WIFI and A/C you can tele-work, while sitting pool side this summer.

Superhost

Tiny home in Ghent

4.95 out of 5 average rating, 131 reviews

Country Getaway Tiny House in Woods w/Pool/Sauna.

Tiny Small House - 600 Sq ft. of new living space on 30 private acres with walkable trains in Beautiful Columbia County. Secluded privacy surrounded by nature. House has everything you need and sleeps 4 with two twin loft beds. Enjoy the pool and renovated barn pool house. In the Winter stay warm by the wood stove. Enjoy the 6 person sauna year round. Restaurants close by or stay in and enjoy the property. Located 9 miles from Hudson and 3 miles from Chatham and Kinderhook. Near OMI Arts Center.

Guest favourite

Home in South Glens Falls

4.92 out of 5 average rating, 37 reviews

3BD-Close to Saratoga & Lake George!

Escape to this 3-bedroom, 1.5-bath haven with an inviting private pool. Relax in the bright living space, cook in the well-equipped kitchen, enjoy cozy bedrooms. Outside, a private fenced poolside oasis awaits - lounge/swim/grill or enjoy the firepit. Explore parks, entertainment, and dining. You are close to it all when you're here. Only 15 min. away from Saratoga, Lake George, skiing, or the gorgeous Adirondacks. Plenty of family memories to be made. This is your ideal year-round retreat!

Guest favourite

Home in Bethlehem

5 out of 5 average rating, 45 reviews

Lakeview Expanse

This is a renovated house situated on 14 acres in Litchfield County, CT. This is a 5 bedroom estate - 1 king size bed, 3 queen beds, 1 bedroom is a dedicated office with a queen size air mattress. 8 guests maximum. Heated saltwater pool (closed until May 2025), 5 seater/1 lounger hot tub, 2 outdoor dining area (one on deck, other on pool patio), 8 seater dining table, 4 seater breakfast table in kitchen, extra large jacuzzi in primary bathroom, wood burning fireplace. Completely private.

Guest favourite

Home in Saugerties

4.94 out of 5 average rating, 70 reviews

Perfect Family Retreat•Pool•Volleyball•Firepit

This stylish, 3-bed, 2-bath home has a plethora of amenities that will keep the kids occupied for hours any time of the year, including a large kids play area in the lower level of the house and a large back yard w newly built FIREPIT area. Close to ski & a back field to build snowmen & sled in winter. In summer, a seasonal heated pool, waterslide & child safety fence, tree house, beach volleyball crt, swing set. Saugerties 10 mins. Relax with the whole family at this peaceful place to stay.

Guest favourite

Home in Saratoga Springs

4.82 out of 5 average rating, 11 reviews

Sunlit 4BD Centrally Located All Things Saratoga

The Saratoga Springs rental you've been searching for! Less than a 10 minute drive from the renowned Saratoga Racetrack, timeless shops and culinary excellence of Broadway, Saratoga Performing Arts Center and picturesque Saratoga Lake. Not only does this home away from home boast 4 large bedrooms, an updated kitchen and plenty of space for every guest - there's also a large patio with outdoor seating to relax and unwind after a day exploring the city! *POOL CLOSED UNTIL MEMORIAL DAY WEEKEND*

Superhost

Home in Litchfield

4.9 out of 5 average rating, 50 reviews

Woodland Country Retreat-Pool+FirePit-nearWineries

20% off JULY/AUG MONTHLY- Leave your worries at the front door of this New England gateway. An open, airy interior may make you feel like staying at home reading all day long, but there's so much to explore nearby. Head out to Black Rock State Park for a scenic hike through lush forests, followed by a leisurely afternoon sampling wines at local vineyards. Gather at this stylish home by the firepit w/loved ones. Pool deck area in rear of house is closed, under maintenance work until 5/26/25

Guest favourite

Home in Hudson

4.93 out of 5 average rating, 243 reviews

Casa Luna Country Retreat with Pool, Hudson, NY

CASA LUNA Perfect peaceful upstate NY country retreat. An all year round escape. 2 hours from NYC driving or Amtrak. 15 mins to downtown Hudson with great restaurants and shopping. 20 mins to water skiing on Copake Lake and 25 mins snow skiing at Catamount, Berkshires. Private & secluded. Columbia County, New York. 4 bedrooms, 2.5 bathrooms, salt water swimming pool, koi pond, claw foot bath tub, steam room. If CASA LUNA is booked check CASA SOL https://www.airbnb.com/rooms/1627143

Guest favourite

Home in Saratoga Springs

4.96 out of 5 average rating, 26 reviews

Serenity-Saratoga Heated Pool, 5 bedrooms, 8 beds

We invite you to come enjoy Saratoga in our newly furnished, stylish raised ranch. Minutes from downtown and the Race Course. Located in a private neighborhood and near Saratoga Performing Arts Center and the State Park. This home is the perfect getaway for relaxation and comfort. Backyard is fully fenced in with an in-ground pool 3-8 feet in depth. The deck is furnished with a patio table/sofas/ gas bbq. Track/SPAC/State Park/Downtown are some of the many ways to enjoy Saratoga.

Superhost

Home in Stanfordville

5 out of 5 average rating, 5 reviews

The Round House w/ Heated Pool

Make some memories at this unique and family-friendly estate. Private & secluded on over 20 acres with heated inground pool this spacious 4 bed, 2 full baths, plus den with sleeping sofa has plenty of space for all. Park-like grounds featuring open fields, picturesque stonewalls overlooking beautiful, heated pool and expansive stone patio where you can entertain or just relax and enjoy nature. Discover effortless living in this fun yet chic dwelling in a remote natural setting.

Top Guest favourite

Home in Saratoga Springs

5 out of 5 average rating, 37 reviews

Saratoga Springs home with heated pool!

You will love this house which is in a quiet neighborhood on a cul de sac! We have upgraded the home with new flooring and baths. New live edge dining table, A new game room featuring a Ring toss, Chess, checkers, new washer and dryer as well. You are centrally located to Downtown Saratoga Springs, SPAC, Racetrack, Casino and more! The town has so much to offer as far as restaurants, shopping, hiking and biking. You are very close to Lake George and Skidmore College as well!

Top Guest favourite

Home in Corinth

4.99 out of 5 average rating, 221 reviews

Beautiful Pool Home between Lk George/Saratoga

POOL is open for the season! Everyone's favorite space here is the backyard patio area! Your own private oasis! Hot tub open all year Recently updated house Beautiful renovated kitchen, 2 separate living rooms, one with comfy sectional and large smart tv, other with reclining couch and woodstove Great location in small town of Corinth, Gateway to the Adirondacks. Located between Lake George and Saratoga 20-25 min away Heated POOL is open til mid Oct. HotTub all year!