
Holiday 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.

midcentury mod * HOT TUB * walk out trail 2 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. fireplace, 5 person hot tub short wooded trail just behind house to access Wallkill Valley Rail Trail, from here walk a scenic mile to R2R trail (take to mohonk) Water St. mkt & the ❤️ of New Paltz Village THE WHOLE PLACE IS YOURS- HOUSE, PROPERTY, POOL (open 5/1-9/30) and HOT TUB (open 9/30-5/1)

Contemporary Guesthouse with Views and Privacy
Secluded studio on 13 acres in Bearsville with views of meadows, mountains and woods. Stand-alone guest house with queen size sleeping loft, kitchenette, fully tiled bathroom, elliptical trainer, and all amenities. Wake up in the morning and enjoy the amazing views with your coffee, hike in the woods, or meditate at the waterfall. In season enjoy the completely private heated pool. End the day with s'mores around the fire pit. An ideal getaway from the city yet only three miles to Woodstock.

Kapitan’s Cottage Private Upstate Catskill Retreat
A vintage rustic country retreat with two floors with modern amenities. 2BR, full & half bathroom. Family & Pet friendly. Large yard surrounded by a mature tree line for secluded privacy. Private stone deck w/ fire pit, BBQ & comfortable deck furniture. Summer Pool access and 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, parks & Ski slopes.

Cozy & 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 + the canoe-ready Roundout Creek. A large sunlit family room, a variety of games, vast outdoor space with patio furniture, in-ground pool/deck/BBQ/swings/firepit/hammock offer the perfect place to relax and restore your connection to nature, friends and family.

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.

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..

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.

Le Petit Abris at Gunks EcoLodge
Now open in Winter, but subject to refunded cancellation if Snow makes the driveway unpassable for those without 4 or all wheel drive. This rental is a small cabin in the woods of New Paltz, NY. The cabin sleeps 4 with 2 twin beds in the loft and has a pullout couch with a quality queen size mattress. The kitchen is equipped but does not have an oven. Streaming TV and Internet. Check out our other listings at the EcoLodge, with Private Rooms/Baths, on the "About Me" page.

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.

Ski & Sauna! Modern Mountain Escape
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.

Full Moon Resort-MSC HikingTrails-Belleayre
These luxury cottages (8 in total) are perfectly nestled on the hillside across from the main property overlooking the untouched Forest Preserve. Each cottage is privately rented individually and surrounded by towering trees the soothing sounds of nature, these serene retreats provide a perfect escape into the wilderness. Each confirmed booking is for ONE cottage only.

The Antique Stone House
A Private Guesthouse in the historic Antique Stone House built in 1810 is awaiting your visit. This Stone House offers a great location in the beautiful Historic City of Kingston, New York, (First Capital of New York State. ) located 90 miles north of Manhattan, for trips, adventures, and outings in every direction. Close to Stockade District and the Waterfront.
Popular amenities for Ulster County rentals with a pool
House rentals with a pool

Shula | Farmhouse | Hot tub, Fire pit, Pool

Woodstock Family Home w/ Tree House + Heated Pool

Bluestone Escape - Where everyone is at home.

Highwoods Haven | saltwater pool and hot tub

BoHo Scandi Farm Retreat, Fireplace, Dogs Welcome

Spacious 5BR Catskill Retreat Near Saugerties Hike

Harrison Field Fall Weekend GetAway ApplePicking

Modern Lux 5-Bed, Double Fireplace, Dogs Welcome
Other holiday rentals with a pool

Hudson Valley Black Barn w/ Firepit + Fireplace

Thorne Hollow - Mountain Ski Getaway with HotTub

The Happy Hemlock

Light-Filled Upstate Home, Perfect Location

Converted Church w/ Pool – Hudson Valley

Tyrolean Style Country House in Saugerties, NY

Pearl In The Woods - Gem with Heated Pool

The Kripplebush Farmhouse: Pool, WBF, Location!
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- Hunter Mountain
- Mountain Creek Resort
- Bethel Woods Center for the Arts
- Belleayre Mountain Ski Center
- Minnewaska State Park Preserve
- Thunder Ridge Ski Area
- Windham Mountain
- Resorts World Catskills
- Bash Bish Falls State Park
- Hudson Highlands State Park
- Kent Falls State Park
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Walkway Over the Hudson State Historic Park
- Catamount Mountain Ski Resort
- Wawayanda State Park
- Taconic State Park
- Sterling Forest State Park
- Plattekill Mountain
- Mount Peter Ski Area
- Hunter Mountain Resort
- Opus 40
- Benmarl Winery
- Warwick Valley Winery & Distillery
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