Vacation rentals with a pool in Ulster

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Ulster

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

Farm stay in Red Hook

4.99 out of 5 average rating, 127 reviews

Sackett & Van Dam Guest House @ Little 9 Farm 1706

Just named one of "The 10 Best Remote AirBnBs for an Escape From Reality" according to the author of 'Leave the World Behind' Rumaan Alam First Floor open space includes a fully equipped Kitchen (Viking Range, Dishwasher, Washer/Dryer, Fridge/Freezer, Caesartone Counters), a Dining Room for 8 and a Living Room with Gas Fireplace & Cable TV Second Floor has 2 Bedrooms: One with a King bed overlooking the paddocks One with 2 Queen beds and a Desk overlooking the pool One bathroom with shower.

Mar 10 – 17

G$128,682 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 21 – 28

G$112,741 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.

Sep 17 – 24

G$143,283 GYD per night

Superhost

Home in Woodstock

4.84 out of 5 average rating, 116 reviews

Modern Woodstock House in the Trees

CALENDAR IS ACCURATE. DON'T ASK FOR BLOCKED DATES. NO EXCEPTIONS FOR: DOGS/PETS or KIDS under 12. We prefer families not groups of friends and do NOT allow PARTIES of any kind. No rentals longer than a week. Pool & hot tub AVAILABLE MAY - SEPT ONLY (no outdoor activities after 10pm). Those who are not forthcoming on intent of their stay will be rejected. We need a strong fit who'll be respectful of our family home, our neighbors & our rules. This is not a generic rental/investment property.

May 17 – 24

G$215,163 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

Jun 3 – 10

G$136,400 GYD per night

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 101 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..

Nov 25 – Dec 2

G$196,770 GYD per night

Guest favorite

Guesthouse in Stanfordville

4.92 out of 5 average rating, 164 reviews

Eco Cottage in the Woods

The cottage is light and airy, surrounded by forest. You may see birds and deer from the bedroom or living room. The queen bed is divided from the living room by a bookcase wall. There is a sofa bed in the living room which faces a patio overlooking the woods. We have a 16x36 unheated gunite pool, professionally maintained. The cottage works well for a couple or a couple with children. 2 night minimum required. Pets welcome. Pet owners passing through may stay 1 night.

Feb 1 – 8

G$28,419 GYD per night

Guest favorite

Cottage in Rhinebeck

4.87 out of 5 average rating, 147 reviews

Secluded peaceful loft in barn by woods

La Barn Bleue sits on top of a hill by a forest, in a secluded and peaceful property. The main house, where we live is 150 feet down the hill. The apartment sleeps up to 4 people. The bedroom/lounge loft has one king bed and 2 twin beds. Ideal for families and kids above 5 years old. Because we used a rope railing, we cannot host kids under 5 years old for security reasons. We offer Wifi, AC/heat split unit, outdoor Picnic table, bbq, petanque court and pool!

Jan 31 – Feb 7

G$33,245 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 7 – 14

G$32,327 GYD per night

Guest favorite

Home in Rhinebeck

4.96 out of 5 average rating, 164 reviews

On The Hill in Rhinebeck

Perched on a hill, this 1930’s cape with a facelift sits just over a mile from the center of Rhinebeck. The first floor is open between the kitchen, dining area and living room. Two private bedrooms and one full bath are also on the first floor. The master suite is up on the second floor with a huge master bathroom featuring a jacuzzi and glass shower. On the hill you’ll experience tree top views and total solitude.

Dec 25 – Jan 1

G$120,733 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 16 – 23

G$38,950 GYD per night

Guest favorite

Cabin in Red Hook

4.96 out of 5 average rating, 306 reviews

Modern Upstate Cabin, near Rhinebeck NY

🏊🏽‍♂️Heated pool is open. (Will be winterized mid October Welcome to Maitopia. This beautifully designed passive glass and wood modern cabin offers elegant modern details and the warmth that only an upstate energy efficient retreat could. With a soaking egg tub, fires at every turn and a heated pool you will fall in love with the place and the towns nearby.

Aug 22 – 29

G$96,981 GYD per night