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Vacation 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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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.

Chalet in Tafton

4.86 out of 5 average rating, 128 reviews

Pocono Chalet~Sauna~Firepit~2 Fireplaces~Game Room

This is a one of a kind LINDAL CEDAR HOME, with an open layout, 16 foot Cathedral ceilings with floor to ceiling windows. Perfect getaway for family outings or friends getting out of the city. Following attractions are nearby: Lakes Wallenpaupack Promised Land State Park Skytop Camelback Ski/tube Kalahari Indoor Water Park Mt. Airy Casino NO PROMS NO FRATS POOL opens mid April and closes mid Nov. All guests are required to accept host's lease agreement prior to check in. Pets need approval

Townhouse in Hudson

4.95 out of 5 average rating, 202 reviews

Palazzo Hudson: Luxury Home with Pool, Spa, Sauna

Welcome to Palazzo Hudson! The only private vacation home in the town of Hudson with a chef's kitchen, seasonal in-ground pool, deluxe sauna, cedar hot tub & the Blue Library-Lounge Barn. A home for all seasons, you'll experience inspiration and relaxation in the warm and whimsical spaces of our unique light-filled home's art, books, music, luxury spa features, outdoor patios, deck, and gardens. A quick stroll to restaurants, bars, cafes, and shops of Warren Street and the Upper Depot District.

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

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.

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

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.

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.

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.

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.

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.

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!

Vacation rentals for every style

Get the amount of space that is right for you

Cabins

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Houses

A space thats all yours, with room for everyone

Cottages

Quaint homes, peaceful surroundings

Popular amenities for Catskill Mountains rentals with a pool

Free parking on premises

Air conditioning

House rentals with a pool

Home in Accord

5 out of 5 average rating, 13 reviews

Newly Built Private Home & Pool

Home in Catskill

5 out of 5 average rating, 16 reviews

NEW! Catskill Family Hideout with Seasonal Pool

Home in Newburgh

4.84 out of 5 average rating, 56 reviews

Entire Home (private pool), Event Friendly

Home in New Paltz

4.93 out of 5 average rating, 133 reviews

Harrison Field Holiday’s In The Hudson Valley

Home in Grahamsville

4.89 out of 5 average rating, 88 reviews

Spacious Catskills Farmhouse on over 5 acres!

Home in Saugerties

4.86 out of 5 average rating, 83 reviews

Unique Contemporary on 40 Pvt Ac, Enclosed Hot Tub

Home in Preston-Potter Hollow

4.9 out of 5 average rating, 29 reviews

Catskill Home w/ Sauna, by ski &Mountain view

Home in Middletown

4.8 out of 5 average rating, 25 reviews

Guest Pool House

Condo rentals with a pool

Condo in Hunter

4.86 out of 5 average rating, 78 reviews

Cozy Gem with Mountain Views

Condo in Windham

4.89 out of 5 average rating, 167 reviews

Cozy Mountain hideaway Windham, Hunter

Condo in Windham

4.94 out of 5 average rating, 32 reviews

Lovely stylish 2-bedroom condo with community pool

Condo in East Jewett

4.96 out of 5 average rating, 28 reviews

Hunter & Windham: Hikes, Lakes, 2BR

Condo in Windham

4.89 out of 5 average rating, 9 reviews

Windham-Hunter Lodge

Condo in Windham

4.92 out of 5 average rating, 59 reviews

4 Bedroom Condo, Close to Golf Courses and Biking

Condo in Windham

5 out of 5 average rating, 4 reviews

Luxury Ski in Ski out Condo + Amenities

Condo in Windham

4.72 out of 5 average rating, 264 reviews

Cozy Condo w/ Wood Burning Fireplace

Home rentals with a private pool

Home in Woodstock

5 out of 5 average rating, 9 reviews

Luxury Retreat in the Catskills

Home in Rhinebeck

5 out of 5 average rating, 69 reviews

Rhinebeck Country Living with a Modern Twist

Home in Bearsville

5 out of 5 average rating, 22 reviews

Magnificent Designer Home - Close To Skiing

Farm stay in Fleischmanns

4.91 out of 5 average rating, 11 reviews

Catskills Hip & Historic Farm Retreat-Near Skiing!

Home in Lagrangeville

4.84 out of 5 average rating, 134 reviews

Classic Hudson Valley Farmhouse Nestled in 9 Rolling Acres

Destinations to explore