
Vacation rentals with a pool in Ulster County
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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)

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise
BoHo Farm House is a luxe, modern 3BR/3BA retreat on 8 stunning acres in Accord, Hudson Valley with a large fully-fenced area for dogs & kids to roam safely. Featured in PureWow, this newly renovated Scandi farm escape includes vaulted wood ceilings, large open living space and chef’s kitchen, cozy fireplace, fire pits, and spa-like ensuite bathrooms. Close to incredible hiking, skiing, and farm-to-table dining. 5 minutes from Inness, Westwind, Arrowood, and the towns of Stone Ridge & Kerhonkson

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.

4Br l Fire-pit l Hot Tub l 10 min to Belleayre
7 min drive to Phoenicia 10 min drive to Belleayre 25 min drive to Hunter 35 min drive to Windham Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-Sept). 6 person hot tub is available year round. Not for parties!! Please be mindful of our neighbors!

Scenic River View Escape | New Paltz
Unwind in nature. House is located on the river bank with river views and surrounded by tall trees with a huge porch and private backyard. The house was recently renovated with all the modern amenities. The place breathes with tranquility and peace and was stylishly decorated with a lot of care and consideration to guests' experience by an experienced host. Just come as you are and enjoy as we have all you need here including top notch complimentary tea, coffee, yoga mats and much more

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.

Dancing Bear Cottage
This gorgeous one room cottage sits at the top of the main property-our wedding couple's favorite. Relax on your private deck. Perfect for sipping your morning coffee, unwinding with a glass of wine, or stargazing under clear Catskill Mountain skies. Experience the serenity of nature. Private driveway allows you to pull right up to your cottage. Features a sitting area with a comfortable couch, a Keurig, compact mini-fridge, custom-tile bathroom, oversized shower, radiant heating.

The Little Shelter 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.

The Harvest Guest House~ Hidden Gem with Pool
Reconnect with yourself & nature. The Georgian style home is set on 6 wooded acres and surrounded by rugged rock ledges, minutes to Marist, The Culinary, Roosevelt & Vanderbilt estates. THE HARVEST GUEST HOUSE offers a genuine Hudson Valley stay. Your suite has its own private entrance, bathroom & fireplace. Enjoy a comfortable place to unwind after exploring nearby trails, river towns, and historic sites. Relaxed, real, and rooted in nature.
Fenced & Salt Water Pool | Cozy Catskills Cottage
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.

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.

Bluestone Escape - Where everyone is at home.
Bluestone Escape is a thoughtfully curated home designed by NYC interior designer Rhobin DelaCruz. Each decision was carefully made with comfort and style as the foundation of all choices. Bluestone Escape isn't just another rental, it's an experience. From hand picked artwork to the simpler detail of USB enabled outlets, Bluestone Escape will feel like the second home you are glad you have.
Popular amenities for Ulster County rentals with a pool
House rentals with a pool

Saugerties Luxury Close to HITS, skiing, hikes

Woodstock Family Home w/ Tree House + Heated Pool

Spacious Winter Retreat Near Woodstock Village

Catskills SKI HAUS Winter Wonderland

Gorgeous Villa MntnViews, nr SKI, firepl, hot tub!

Highwoods Haven | saltwater pool and hot tub

MODERN FARMHOUSE in the WOODS

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

Luxe Mountain Getaway|Fire Pit|Arcade|Hot Tub|Pool

Newly Built Private Home & Pool

Kapitan’s Cottage Private Upstate Winter Retreat

The Lodge | Grateful Woods Retreat w/ HT, FP, Farm

bungalow summer cottages on the lake Catskills

Cheerful 3-bedroom Cabin in the Woods with a pool.

Woodstock 3BR Bungalow | Ski, Steam, Fireplaces

Beautifully Renovated Woodstock Cabin with Sauna
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- Hunter Mountain
- Mountain Creek Resort
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Thunder Ridge Ski Area
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Resorts World Catskills
- Windham Mountain
- Mount Peter Ski Area
- Hunter Mountain Resort
- Bash Bish Falls State Park
- Kent Falls State Park
- Plattekill Mountain
- Brotherhood, America's Oldest Winery
- Zoom Flume
- Bear Mountain State Park
- Taconic State Park
- Wawayanda State Park
- Opus 40
- Benmarl Winery
- Warwick Valley Winery & Distillery
- Millbrook Vineyards & Winery
- Mohonk Preserve
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