Vacation rentals with a pool in Ulster County

4.98 out of 5 average rating, 489 reviews

Home in New Paltz

midcentury mod * POOL * walk out trail to 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. 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 Several outdoor seating areas. THE WHOLE PLACE IS YOURS FULL PRIVATE ACCESS HOUSE, POOL & PROPERTY POOL OPEN 5/1 - 9/30

4.96 out of 5 average rating, 120 reviews

Cottage in Bearsville

Contemporary Guesthouse with Private Heated Pool

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.

4.99 out of 5 average rating, 138 reviews

Cottage in Saugerties

Black Ridge Cottage: Pond, Cowboy Pool & Sauna

Kick back and relax in this calm, stylish space, with private wildlife filled pond & cowboy pool This house is great for a family, or two couples. There are lots of relaxing spaces inside and several seating areas in nature outside. Ten minutes to the towns of Woodstock and Saugerties, you will have the perfect location to enjoy the best experiences the Hudson Valley has to offer. This 4 bedroom, 3 bath house has been recently gut renovated. Enjoy the beautiful design and natural landscape.

4.92 out of 5 average rating, 377 reviews

Cottage in Kingston

Kapitan’s Cottage: Private Retreat with Salt Pool

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.

4.98 out of 5 average rating, 146 reviews

Home in Woodstock

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..

Superhost

Cabin in Kerhonkson

4.95 out of 5 average rating, 148 reviews

Pool - Hot Tub - Game Room - Mini Golf - Country

Welcome to our renovated Catskills oasis on the Rondout Creek and Rail Trail, minutes from Minnewaska and the Gunks! Unwind in the year-round covered hot tub, lounge by the pool, gather around the fire pit, or play mini golf under the stars. Inside, relax by the fireplace or hit the speakeasy-style game room with pool, ping pong, Pac-Man, Pop-a-shot, darts, a bar, and TV. We offer private chefs, local meats, and top picks for hikes, bites, and watering holes. Yes, we love pets! 🐾

Superhost

Cabin in Kerhonkson

4.83 out of 5 average rating, 241 reviews

Secluded Home: Pool, Sauna Tennis & Trails

Welcome to your perfect all-inclusive Catskills getaway. Secluded hilltop cabin in the woods. Cozy home features 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

4.95 out of 5 average rating, 363 reviews

Home in Kerhonkson

Beautiful Salt Water Pool & Fully Fenced 10 Acres

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.

4.99 out of 5 average rating, 138 reviews

Cabin in Saugerties

Lovely cabin by the stream

We are close to HITS, Hunter Mtn and all of the wonderful activities of the Hudson Valley. This is a very peaceful cabin, steps from the stream. We are perfect for single guests or a maximum of two people (including children) as the cabin is quite small. The cabin is private and set in the woods, yet steps away from the pool, sauna, screen house. We are a carbon neutral property, with a large solar array and a Level 2 EV charger.

4.94 out of 5 average rating, 373 reviews

Guest suite in New Paltz

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.

4.89 out of 5 average rating, 268 reviews

Cottage in Pine Bush

Seclusion and Romance - Pool is open and heated!

Amazing 5 Star guest house. Pool is open and heated! Outdoor living room with a wood fireplace. Close to many attractions: hiking, wineries, breweries, restaurants, Sam's Point, etc. Romantic, high end getaway. Amenities: charcoal BBQ, mini fridge, propane grill, full bath, microwave, wood fireplace, fire pit, single induction hot plate, wifi, smart TV, Firewood and fire bricks available.

4.97 out of 5 average rating, 120 reviews

Cabin in Arkville

Hike & 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.

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Chalets

Adventure-ready homes with après-ski style

Popular amenities for Ulster County rentals with a pool

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

5 out of 5 average rating, 20 reviews

Home in Accord

Newly Built Private Home & Pool

KannaRating, 5 stars1 week ago

This was our second time back at the house and we felt right at home. The house is beautiful, exceptionally clean and well taken care of. Everything is well thought out for guests. The space is perfect for entertaining and relaxing with friends and family. There is really no need to venture out since everything is at your fingertips - from the pool, the fire pit, the grill and large open spaces to hang out both inside and outside. It’s very well situated and close to a number of great places in the area including Inness and Cherries. We celebrated our sister’s birthday at the house and it was perfect - made a lot of lasting memories, with friends and family. Amy was extremely responsive throughout the whole process and very thoughtful. We are very familiar with the area but she made great suggestions for us to visit, that we hadn’t heard of before. We will definitely be back!

4.87 out of 5 average rating, 134 reviews

Home in Woodstock

Gorgeous Villa Mntn Views, salt H2O pool, hot tub!

JenaRating, 5 stars1 month ago

Beautiful view, great space for our girls weekend trip!

4.94 out of 5 average rating, 144 reviews

5BR close to Village | Diamond Mills | HITS | Pool

JimenaRating, 5 stars2 weeks ago

We had a great time at Saugerties! Rebecca's house was wonderful. The heated pool and the trampoline were the kids' favorite and they kept them entertained all day. The adults enjoyed the shade under the comfy pool lounge chairs & the spacious deck furniture. The backyard of the house was well kept and equipped so we spent a lot of time outside. The house is very well equipped and it was spacious for 2 families of 4. Everything was functioning well. The house is close to downtown and there are plenty of things to do nearby. Host was super quick to respond back and to help with whatever we needed right away. We def recommend Rebecca's house.

4.95 out of 5 average rating, 108 reviews

MODERN FARMHOUSE in the WOODS

BenjaminRating, 5 stars8 months ago

We had a terrific stay. The house was exactly as advertised.

5 out of 5 average rating, 152 reviews

Upstate Modern Scandinavian Barn in the Catskills

Zoe StarRating, 5 stars3 weeks ago

We truly enjoyed our stay at Wilderkill Barn. Maria Cristina and William were exceptional hosts—warm, attentive, and genuinely committed to making our visit special. They went above and beyond to make us feel welcome. The home was a haven, with a hot tub, sauna, pool, fire pit, pool table, and immersive sound and movie systems—all of which made our stay delightful despite the cold, dreary May weather. We can't thank them enough. ***That said, we feel it's necessary to address a serious issue with Airbnb itself that arose while booking this property, unrelated to the property itself. An unexpected tax was added after booking, and Airbnb has yet to provide a clear explanation. After years of loyalty, we were disappointed by their evasive and unhelpful customer support. This experience has made us reconsider using the platform in the future. We urge potential users to scrutinize all fees carefully and be aware that Airbnb’s support may be difficult to navigate if problems arise.***

4.91 out of 5 average rating, 23 reviews

Home in Kerhonkson

Tranquil Retreat in Kerhonkson

NazlyRating, 5 stars2 weeks ago

What a wonderful place!! One of my favorite airbnbs thus far & I’ve been to MANY. Had so many amenities in the kitchen which was very useful since we cooked for the 3 days we were here. The house is beautiful, the hot tub is perfect, and the bathrooms!! Absolutely stunning. The shower is relaxing & the bathtub is even more relaxing! Also loved the fact they have a record player with tons of options. Had such a memorable experience dancing with my newborn in the lovely living room to frank sinatra. I would definitely come again! Thank you for having us!