Holiday rentals with a pool in Catskill Mountains

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Catskill Mountains

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

4.95 out of 5 average rating, 132 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.

Superhost

Cabin in Swan Lake

4.83 out of 5 average rating, 196 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

This designer home is in the western Catskills, 2hrs away from NYC on 10 acres of hillside property. 20 mins from the Kartrite indoor water park. Perfect family getaway for hiking, canoeing, fishing , water sports. Quiet, secluded, fully stocked kitchen, 360 degree views , patio deck seating private heated pool from May 20- Sept 30 cabana, hammock, loungers Starting March 1st 2021, we are offering our newly installed Hot Tub/ Spa ( 5-6 seater) set into the side of hill w/ magnificent views

Guest favourite

Home in Saugerties

4.94 out of 5 average rating, 65 reviews

Perfect Family Winter Retreat•Close to Ski•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 Hudson

4.93 out of 5 average rating, 242 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 Stone Ridge

4.98 out of 5 average rating, 100 reviews

Stone Ridge Retreat with Heated Pool & Hot Tub

Our renovated home is situated on 4 acres of private property, just two hours north of NYC. The house is a short drive from Woodstock, the Catskills and Shawangunk mountains. It's perfect for any weekend get away or vacation with family and friends. The days are perfect for sightseeing while the nights are cool enough to enjoy our hot tub after a day spent hiking in the Catskills. My Pool is now closed until next summer. Terrific Wifi with speed up to 300 Mbps. Pets are allowed.

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 favourite

Home in Kerhonkson

4.95 out of 5 average rating, 348 reviews

Winter Wonderland: Dog & Family Friendly Chalet

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.

Superhost

Home in Lake Ariel

4.87 out of 5 average rating, 125 reviews

Beautiful Lakeview - Ski Hill & Indoor Courts

Cozy Lakeview home with large deck,BBQ & fire pit in a safe family-friendly community with lots of amenities! Steps away from the pool - close to beach/lake area. HOME HAS AIR CONDITIONING! Community has 2 Lakes and pools with beach/BBQ area. All you need for a fun-filled and relaxing getaway. Basketball & Tennis Courts, Kayak rentals and more... Winter -The Hideout offers snow tubing and skiing. Guests are responsible for lift tickets, rentals and any other fees for use.

Guest favourite

Home in Woodstock

4.85 out of 5 average rating, 123 reviews

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

Our beautiful Villa has amazing mountain views, a clean, modern design and is the perfect getaway to socialize & relax. It is ideally located for hiking & has a gorgeous, private salt water pool (mid May- mid Oct) and a wonderful hot tub which is open year round! Please check for pool opening/closing. In addition to the main house there is also a studio cottage (with bathroom) that can be used as a WFH private office. It has it's own high speed internet.

Guest favourite

Home in Narrowsburg

4.95 out of 5 average rating, 179 reviews

Mid-Century Modern House with Fireplace & Hot-Tub

The House of Modern Art, perched atop a hill and embraced by a picturesque landscape. This home is tastefully furnished and decorated with the intention of creating a peaceful sanctuary, while reflecting an urban sense of style and timeless aesthetic of Mid-Century Modern design. Comfortable yet sophisticated, this home has all the amenities for seamless year-round livability, guaranteed to inspire you and ensure a relaxing experience.

Guest favourite

Home in Goshen

4.89 out of 5 average rating, 9 reviews

Beautiful home with heated pool

Escape to this spacious 4,700 sq. ft. retreat on 3 private acres, perfect for family gatherings or group getaways. With 5 bedrooms and 3.5 bathrooms, this home offers ample space and natural light from expansive windows. Enjoy the walkout basement complete with a billiard room, wet bar, and direct access to a heated pool for ultimate relaxation. Experience the best of comfort and privacy in this serene setting – your ideal escape awaits!