Vacation rentals with a pool in The Berkshires

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in The Berkshires

Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Averill Park

4.95 out of 5 average rating, 136 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 favorite

Guesthouse in Southbury

4.93 out of 5 average rating, 318 reviews

Charming Guest Cottage with Modern Amenities

Private Guest House set on 5+ Acres, along with Historic Colonial Home. Bright and sunny and over looks pool and gardens (seasonal). Efficiency with Kitchen featuring 2 burner stove, Microwave, Under Counter Fridge/Freezer/Ice Maker, Dishwasher, Granite Counters. . Dining Area, Great Room w/ soaring ceilings, French Doors to private patio, hardwood floors. Loft with full-sized bed, and sofa can be a to Queen Size Sleeper. Full bath with extra-large shower. Dog friendly (approval needed).

Guest favorite

Home in South Glens Falls

4.94 out of 5 average rating, 36 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 favorite

Home in Saugerties

4.94 out of 5 average rating, 68 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.

Top guest favorite

Home in Corinth

4.99 out of 5 average rating, 219 reviews

Beautiful Pool and hot tub Home Adirondacks

Everyone's favorite space here is the backyard patio area! Your own private resort! 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. Moreau State Park, West Mtn Ski Area. Heated POOL is open mid May til mid Oct. HotTub all year!

Guest favorite

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, 49 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

Top guest favorite

Home in Gloversville

4.97 out of 5 average rating, 352 reviews

Indoor Heated Pool in the Adirondacks

Year round indoor pool house that is 2000 square feet located in the lower adirondacks. There are several outdoor activities to do in the area...fishing, boating, hiking, kayaking, snowmobiling,cross country skiing & restaurants. Check out my guidebook with things to do in and around the area including near by lakes and restaurants on the lakes. Spend the day exploring and then come back to relax in the warmth of your very own private pool, sit by a fire on the patio or start the grill.

Guest favorite

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

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.

Guest favorite

Home in Kerhonkson

4.95 out of 5 average rating, 354 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

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What guests are saying

Charming lakeside cabin with private heated pool

4.96 out of 5 average rating, 48 reviews7 months ago

My family and I stayed for a long weekend and were so glad that we did! It’s a beautiful cabin, with all the things you need. Kitchen is stocked with essentials, enough bathrooms, beds are super comfortable, hooks to actually hang things like towels, jackets… but we loved the outdoors even more! We walked to the lake, spent way too many hours in the pool, grilled, lounged, made s’mores by the fire pit and watched the beautiful stars at night. Couldn’t ask for more. Paula and her lovely family are SO welcoming it’s crazy. 😂. Hope to be back next summer!

Home in Stanfordville

What guests are saying

Exquisite family friendly home with heated pool!

5 out of 5 average rating, 4 reviews9 months ago

We had a wonderful family vacation staying at Stone Hill. The house is absolutely perfect, literally a dream house. The pool and landscaping are beautiful and peaceful. The kitchen has everything you could ever need for cooking big meals. We thoroughly enjoyed the basket with s’mores ingredients and the fire pit. The screened-in porch was the perfect spot to enjoy morning coffee and look out at the scenery and pool. The ping-pong table in the basement was fun for the whole family, as well as a great selection of games and cards in the TV room. These came in handy on our 2 rainy days. The owner was super responsive to a few questions we had. It’s the perfect location, only a short drive to Great Barrington and grocery shopping at Guido’s. There’s also a great dog park in GB if you’re traveling with a dog. We hope to come back to Stone Hill many times in the future.

Home in Egremont

What guests are saying

Mountain View Townhome w/ Community Pool!

5 out of 5 average rating, 12 reviews12 months ago

Anne is an amazing host and this townhouse is fabulous. Perfect for a mountain stay. Comfortable, spacious, great view of the mountain, clean, modern yet cozy. Very convenient to everything in the area. I cannot say enough about it, but having such a great host was the cherry on top, especially since we were there for an extended period!! You cannot go wrong!

Condo in Hunter

What guests are saying

Serene Country home 24 mi Mohawk ski area

4.94 out of 5 average rating, 32 reviews1 month ago

A beautiful home- super comfortable and spacious. It is outfitted with everything you could need. Peaceful location (we stayed in spring/winter- can’t speak to what it would be like in season). Lovely views. Easy to get into town by car (3-5 minutes!). Host was excellent - responsive to any questions or inquiries

Home in New Milford

What guests are saying

Beaver | Pool, Firepit, Secluded, 10 acres

4.83 out of 5 average rating, 70 reviews2 months ago

We had an absolutely wonderful stay at Hava’s Airbnb! From the moment we booked, Hava was an incredible host—warm, welcoming, and unbelievably reachable. She responded to every question we had almost instantly, whether it was about check-in details or local recommendations, making the entire experience seamless and stress-free. The place itself was spotless, cozy, and exactly as described, with thoughtful touches that made us feel right at home. Hava’s communication stood out—she checked in to ensure everything was perfect without ever being intrusive. Her suggestions for nearby spots were spot-on, and it’s clear she genuinely cares about her guests’ comfort. We couldn’t have asked for a better host, and we’d love to stay here again. Highly recommend Hava to anyone looking for a fantastic Airbnb experience!

Home in Kingston

What guests are saying

Saratoga Musical Oasis|Heated Pool|King Bed|Views

4.88 out of 5 average rating, 8 reviews3 months ago

The pictures posted on the listing of this house do not do it justice. This house was beautiful. While located on a convenient road, there was not another house in sight for a nice sense of privacy. The mud room itself is a huge bonus to off load gear and supplies and keep them organized without cluttering up the entire house. The ensuite bathroom in all 3 bedrooms was a pleasant surprise with the master bath being one of the best I've ever experienced. The state of the art TV, lighting, thermostat and surround sound system does take some getting used to and would definitely be a challenge to the elderly and non tech savvy. Great overall experience. Would love to stay again when the pool is open.

Home in Greenfield Center

What guests are saying

Private Contemporary Cottage with Pool and Hot Tub

4.8 out of 5 average rating, 5 reviews3 months ago

This house is a gem. Admittedly it’s far from home if you are coming from NYC, which is where my family is. However, the upside is that this house is beautiful, on a big private area, and the absolute perfect place for a getaway with kids. We were three families with three little girls who hopefully made forever memories. I hope we will be back again soon!

Home in Roxbury