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.

0 of 0 items showing

1 of 3 pages

Guest favorite

Cabin in Livingston Manor

4.96 out of 5 average rating, 257 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

Feb 17 – 24

R12,176 ZAR per night

Guest favorite

Home in Kerhonkson

4.89 out of 5 average rating, 139 reviews

Black Barn Ranch, Catskills.

Welcome to Black Barn Ranch House, a modern Scandinavian getaway at the foothills of the Catskills, just 2.5 hours from NYC. This 3 bedroom, 2 bath features an open floor plan, over-sized windows with an abundance of natural light and mountain views, and thoughtful touches of comfort throughout. Also an indoor fireplace and an outdoor saltwater pool ** Pool is closed for the season**. This welcoming destination is great for all wanting to explore the Hudson Valley and create lasting memories.

Jun 12 – 19

R20,298 ZAR per night

Guest favorite

Home in Saugerties

5.0 out of 5 average rating, 132 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. Building 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.

Oct 27 – Nov 3

R12,926 ZAR per night

Guest favorite

Home in New Paltz

4.98 out of 5 average rating, 435 reviews

midcentury modern in ground pool walk 2 trail/town

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 - end of SEPTEMBER

Nov 26 – Dec 3

R15,064 ZAR per night

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 100 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..

Dec 5 – 12

R15,298 ZAR per night

Guest favorite

Home in Kerhonkson

4.94 out of 5 average rating, 325 reviews

Country House: Rustic Charm With Modern Feel

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.

May 16 – 23

R7,386 ZAR per night

Guest favorite

Guesthouse in Margaretville

4.99 out of 5 average rating, 134 reviews

Sunny Arts & Crafts Loft

Catskill Mtn. Summer: hiking, swimming, relaxing. Explore fun towns like Margaretville, Andes & more. May & June are almost fully booked, but lots of great summer and fall dates available. Situated on a peaceful mountainside, the loft is a cozy, private place to unwind as you enjoy a Catskill Mtn. adventure. Super savings on longer stays, too! Our road is plowed & sanded, but you will definitely need AWD & good tires to ensure smooth travels in the WINTER months.

Feb 7 – 14

R1,911 ZAR per night

Guest favorite

Chalet in Olivebridge

4.98 out of 5 average rating, 124 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. Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Jun 5 – 12

R9,590 ZAR per night

Guest favorite

Cabin in Saugerties

4.99 out of 5 average rating, 123 reviews

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.

Aug 3 – 10

R2,916 ZAR per night

Guest favorite

Guesthouse in Kingston

4.92 out of 5 average rating, 288 reviews

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.

Sep 30 – Oct 7

R3,514 ZAR per night

Guest favorite

Apartment in New Paltz

4.93 out of 5 average rating, 280 reviews

Sweet Suite on Beautiful Mountain Road *Pool*

Relax and unwind in a spacious and private suite located close to Mohonk Preserve. This independent space features a king bed in the main space, a queen bed in a separate bedroom, a well-appointed kitchen/kitchenette, and a small full bathroom. The space is sunny, with views of the woods and our large yard. The vibe is restorative and comfy.

May 8 – 15

R2,294 ZAR per night

Guest favorite

Cottage in Kingston

4.81 out of 5 average rating, 146 reviews

Cottage w/ Deck @woodstockwellnessplace

Guest house on 8 acre property with forest and pond. Rental includes your own tiny home with large bathroom, private deck with grill and fire pit and access to pool on main deck (May ish- September ish)via a path from your deck in warm months. Swim access from 10am to 6pm. Pool shared with others staying in main house.

Jun 26 – Jul 3

R2,833 ZAR per night