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.

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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 12 – 19

G$147,694 GYD per night

Guest favorite

Cottage in Kingston

4.91 out of 5 average rating, 303 reviews

Kapitan's Cottage: Tranquil, on 7 acres. Pool.

Idyllic country retreat featuring two floors with modern amenities. Full, and half bathroom and very family friendly. Situated close to Kingston, High Falls & Stone Ridge, yet just far enough out to feel you're away from city hustle and bustle. 45 mins to Ski slopes. Private stone deck with fire pit, BBQ & comfortable deck furniture Summer season In-gound heated saltwater pool 16 x 40’ - technically shared with us but in reality you’ll likely have it to yourselves the majority of the time.

Jul 30 – Aug 6

G$115,539 GYD 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.

Dec 29 – Jan 5

G$143,657 GYD per night

Guest favorite

Home in New Paltz

4.98 out of 5 average rating, 437 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

Jul 14 – 21

G$191,276 GYD 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..

Jan 25 – Feb 1

G$170,024 GYD 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.

Sep 17 – 24

G$130,843 GYD 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.

Jul 24 – 31

G$21,243 GYD 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

Sep 29 – Oct 6

G$141,604 GYD 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.

Oct 4 – 11

G$32,411 GYD 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 29 – Oct 6

G$39,052 GYD 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.

Jul 10 – 17

G$31,894 GYD per night

Guest favorite

Guest suite in New Paltz

4.84 out of 5 average rating, 181 reviews

Private apartment in rural home

Enjoy privacy and convenience in our ground-level 3-room apt. You can sleep late in the quiet space, or rise early, watch the birds, and go for a walk. Just a hop-skip to town, and a few minutes to the mountains. Guests love a dip in the pool after a day of hiking, or float around watching the hummingbirds above you.

Mar 27 – Apr 3

G$26,051 GYD per night