
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.

Scenic River View Escape | New Paltz
Unwind in nature at this scenic New Paltz escape, located on a serene riverbank with spectacular views. Large porch and private backyard are perfect for relaxation and stargazing. Recently renovated, the house blends modern amenities with a tranquil atmosphere. Thoughtfully designed, it features a cozy fireplace, large smart TV, and fully equipped kitchen. Explore nearby hiking trails, waterfalls, and Minnewaska State Park, or relax in the hot tub. Ideal for couples, families, and remote workers
4.88 out of 5 average rating, 243 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
4.99 out of 5 average rating, 279 reviews
Comfortable & Spacious Country Home - All Seasons
We welcome you to stay at our inviting home in the hamlet of High Falls. The two-story early 1900's era farmhouse is set on 12 private acres off a quiet country road in a lovely residential area. Grounds feature access to woods, pond and canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with furnished patio, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.
4.98 out of 5 average rating, 123 reviews
midcentury mod hot tub*walk out trail R2R/Mohonk
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. IN GROUND SWIMMING POOL & HOT TUB short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk to an organic farm? A scenic mile to R2R trail to Mohonk, Water St. mkt & the Village of NP WHOLE PLACE IS YOURS HOUSE & PROPERTY POOL May 1 - Sept 21 HOT TUB YEAR ROUND
4.98 out of 5 average rating, 549 reviews
Upstate Modern Scandinavian Barn in the Catskills
Renovated 1850's barn with 3 bedrooms and an ample loft space that can serve as a fourth. The house also has a large rec room with cathedral ceiling buttressed by hand-hewn beams, well-equipped kitchen, Scandinavian wood stove, sauna, home gym, and projector. Outside: 2 private decks with amazing views of Overlook Mountain, private grill, private hot tub. On property: shared tennis court, swing set, fishing pond, heated pool (summer only). 2 hours from NYC, 10 min. to Woodstock & Saugerties.
5.0 out of 5 average rating, 173 reviews
Experience The Zen House
Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & 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! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & much more!
4.97 out of 5 average rating, 365 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..
4.96 out of 5 average rating, 185 reviews
Spacious Catskills Farmhouse on over 5 acres!
Come enjoy autumn in the Catskill Mountains! Fall is the best time to visit the Catskills. Crisp nights, fresh apple cider, U-pick farms, bonfires, and picture-perfect fall foliage. Get outside to explore our local trails, parks & lakes. Enjoy a round of golf, or visit the casino or indoor waterpark. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four-season recreation.
4.91 out of 5 average rating, 127 reviews
Peace & Privacy - High Falls (hot tub & salt pool)
Enjoy the serenity of this contemporary home on six private acres central to all the Hudson Valley has to offer; just 20 min. from the NYS Thruway. Year-round hot tub, seasonal salt water pool, fireplace, gourmet kitchen, and large deck & patio w/ fire pit make this the ultimate getaway. Sports enthusiasts, shoppers, and diners will delight in how close we are to amazing Catskills attractions. New Paltz, Kingston, Mohonk Preserve and Minnewaska State Park are just 15 minutes away.
4.96 out of 5 average rating, 312 reviews
Luxe modern A Frame, Hot tub and new heated pool
Experience the luxury of this black double A-frame, finished to the highest standards and nestled in the woods for ultimate privacy. The main bedroom features a soaring ceiling and spa-like en-suite with walk-in shower, tub, bidet, double sink, and heated floors. The sunny second bedroom also has an en-suite. Enjoy a chef’s kitchen, double-sided fireplace, hot tub, and a new pool available June. Pets must be disclosed and approved prior to booking.
4.97 out of 5 average rating, 120 reviewsA Very Cozy House With a Very Big Yard
The perfect spot to unwind with family, friends, and pups. Spend the day hiking, visiting farms, or trying local restaurants, then come home to the yard for kid-and-dog frolicking, “Squirrel TV” through long windows. Soak in the claw-foot tub or the jetted spa tub, then gather by the fire with wine and board games. Swim and make s’mores in summer, watch snow fall in winter, and enjoy peaceful views in every season, relax, play, laugh, repeat.
4.94 out of 5 average rating, 414 reviews
Ski & Sauna! Modern Cabin - Minutes to Bellayre
Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.
4.98 out of 5 average rating, 176 reviewsPopular amenities for Ulster County rentals with a pool
House rentals with a pool

Woodstock Getaway - Heated Pool/Hot Tub/FirePit
4.98 out of 5 average rating, 129 reviews
Secluded Woodstock Retreat -Heated Pool and Sauna
4.97 out of 5 average rating, 163 reviews
Luxury Retreat with pool in historic Kingston
5.0 out of 5 average rating, 129 reviews
Viewtop Farmhouse-Fall in the Hudson Valley
4.94 out of 5 average rating, 141 reviews
Gorgeous Villa Mntn Views • POOL • hot tub •grill!
4.88 out of 5 average rating, 155 reviews
New Paltz dog friendly retreat w/ salt water pool
4.97 out of 5 average rating, 181 reviews
Peaceful Hudson Valley Getaway
4.93 out of 5 average rating, 128 reviews
Enjoy Pool, Bocce Court, Fire Pit -Close to HITS
5.0 out of 5 average rating, 113 reviewsOther vacation rentals with a pool

Hot Tub - Sauna - Arcade- Fireplace - Pool Open
4.89 out of 5 average rating, 213 reviews
Airy & Private Escape on Mountain Rest Road *Pool*
4.95 out of 5 average rating, 456 reviews
Enchanting Upstate Cabin w Pool, Firepit
4.9 out of 5 average rating, 144 reviews
Black Ridge Cottage: Pond, Cowboy Pool & Sauna
4.97 out of 5 average rating, 176 reviews
Grapevine Cottage
4.99 out of 5 average rating, 382 reviews
Modern Getaway in Kingston - 1.5hr from NYC
4.91 out of 5 average rating, 117 reviews
Contemporary Guesthouse with Heated Pool
4.97 out of 5 average rating, 151 reviews
Sweet Fern Cottage With Saltwater Pool
4.93 out of 5 average rating, 288 reviewsDestinations to explore
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- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Bear Mountain State Park
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Bethel Woods Center for the Arts
- Resorts World Catskills
- Windham Mountain
- Catamount Mountain Ski Resort
- Storm King Art Center
- Taconic State Park
- Plattekill Mountain
- Mohonk Preserve
- Mountain Creek Water Park
- Peekamoose Blue Hole
- Hunter Mountain Resort
- Kent Falls State Park
- Bash Bish Falls State Park
- Brotherhood, America's Oldest Winery
- Harriman State Park
- Mount Peter Ski Area
- Wawayanda State Park
- Millbrook Vineyards & Winery
- Things to do Ulster County
- Art workshops Ulster County
- Outdoors Ulster County
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- Cooking New York
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- Shopping and fashion New York
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- Museums New York
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- Dining New York
- Wildlife New York
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