Vacation rentals with a pool in Ulster County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ulster County

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

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Guest favorite

Home in Woodstock

4.99 out of 5 average rating, 249 reviews

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

Guest favorite

Cabin in Livingston Manor

4.97 out of 5 average rating, 280 reviews

Experience The Zen House

Enjoy your own private indoor HD movie theater with 5.1 Bose Surround Sound and leather recliner seats, a spa with a cold plunge pool and sauna, and a hot tub to reach the maximum level of relaxation. Play a game of ping pong, enjoy the fireplace outside and inside along with 5 acres! Here are some of the key amenities: -Hot Tub (2021) -Sauna & Cold Plunge Pool -Private 12 Person Movie Theater (you can plug in your device) -Table Tennis/Ping Pong and much more! Check us out on ig: @zenhouseny

Superhost

Cabin in Kerhonkson

4.82 out of 5 average rating, 229 reviews

Secluded Home: Sauna Tennis & Trails 2 hrs frm NYC

Welcome to your perfect all-inclusive Catskills getaway. Secluded hilltop cabin in the woods. Cozy home features salt-water heated pool, sauna, large 2000sf deck overlooking forest, full size tennis court, 15.5 acres for hiking, fishing, and exploring. Located only 2 hours from New York City & 20 mins from Woodstock. Two-bdrm house with one full bathroom and loft sleeping space. House is located on a quiet road. Turn into the private driveway and get ready to relax and mingle with Mother Nature

Guest favorite

Home in Woodstock

4.92 out of 5 average rating, 238 reviews

Little owl Japanese teahouse: pool and tennis

You will love our secluded country estate, just a short drive to Woodstock, our authentic Japanese teahouse is the ideal combination of away-from-it-all and convenience. Enjoy sweeping Mountain View’s from your heated bed after a day of shopping, dining, or hiking, if you’re here when the trees are turning golden brown in autumn, snowy in winter or when the sun shines in summer, barbecues by the fire pit beneath the string lights and swims in the salt pool, a game of tennis or bbq by the fire!

Guest favorite

Cottage in Kingston

4.92 out of 5 average rating, 344 reviews

Private Upstate Rustic Getaway Kapitan’s Cottage

A vintage rustic country retreat featuring two floors with modern amenities. 2BR, full, and half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck with fire pit, BBQ & comfortable deck furniture. Generator on site. Close to Kingston, High Falls, Stone Ridge and Woodstock yet just far enough out to feel you're away from city hustle and bustle. Close to miles of hiking, outdoor activities and parks. 45 mins to Ski slopes.

Superhost

Cottage in Kerhonkson

4.82 out of 5 average rating, 165 reviews

Gunks Cottage|Fire Pit|Pool|Near Minnewaska Park

This charming 2-bedroom cottage is nestled on an acre of private, untouched wilderness, making it a great place for nature lovers, hikers, and couples looking for the perfect getaway. When you’re not exploring Minnewaska State Park, enjoy the pool, stargazing from next to the fire pit, and soaking tired muscles in the hot tub. 6 Min Drive to Minnewaska State Park Preserve 10 Min Drive to Stony Kill Falls 15 Min Drive to Wightman Fruit Farm Experience Kerhonkson With Us & Learn More Below!

Guest favorite

Home in Kerhonkson

4.94 out of 5 average rating, 109 reviews

Modern Lux 5-Bed, Catskill view, Dog Friendly!

Beautifully renovated mid-century modern retreat! With 5 private bedrooms, 3.5 bathrooms, 2 spacious living rooms, a double-sided fireplace, and a mini grand piano, this space is perfect for families, groups, or couples seeking a romantic escape. Enjoy the seasonal heated saltwater pool in summer and relax in a dog-friendly, fenced area just under two hours from NYC via New Paltz. Experience breathtaking views and complete privacy in the stunning Kerhonkson area. The pool is now closed.

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 123 reviews

Woodstock Historic Artist Estate- The Museum House

The property is an estate formerly owned by renowned artist Reginald Marsh located within a 10 minute walking distance to the center of the historic town of Woodstock, NY. The 2500sft house is the former Museum House that used to hold Mabel Marsh’s art collection that was later acquired by the Smithsonian Institute. It has been architect gut-renovated into a dramatic living experience surrounded by nature and water. The Pond and Carriage House are at the opposite side of the estate..

Guest favorite

Chalet in Olivebridge

4.99 out of 5 average rating, 144 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees, oh, and now a Projector TV in the basement! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Guest favorite

Home in New Paltz

4.98 out of 5 average rating, 467 reviews

midcentury mod fireplace walk 2 hiking trl/village

A Frank Lloyd Wright inspired Mid Century Mod w updated amenities, comfy, clean, open concept. Large windows offer big views of flora/fauna and the many birds & wildlife. Mtn views including skytop. short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail Water St. mkt & the ❤️ of New Paltz Village. Several outdoor seating areas. The whole place is yours FULL PRIVATE ACCESS TO HOUSE/PROPERTY POOL OPEN MAY 1 - OCT 1

Guest favorite

Home in Kerhonkson

4.95 out of 5 average rating, 345 reviews

Cozy Country Cabin for Dogs, Families & Friends

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.

Guest favorite

Guest suite in New Paltz

4.94 out of 5 average rating, 339 reviews

Airy & Private Escape on Mountain Rest Road *Pool*

Relax and unwind in our bright and private 2BR apartment located at the edge of Unison Arts Center’s sculpture garden (paths through woods and fields). A mile from New Paltz on the way to Mohonk Preserve, this simple but comfortable space features work by local artists and regional photographs. One of the bedrooms has an additional half-bathroom with a hand-made mosaic. Guests have their own entrance.