Vacation rentals with a pool in Sullivan County

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Sullivan 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

4.97 out of 5 average rating, 279 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

Guest favorite

Home in Middletown

4.94 out of 5 average rating, 113 reviews

Cozy Autumn Farm Country Escape with Hot tub.

Looking for a perfect Winter upstate retreat? Look no further! Welcome to our beautiful 100 year old farmhouse! Nestled on over two acres in the Southern valley of the Shawangunk mountains, this is a beautiful area to explore foliage and hikes, stay home to soak in the hot tub, warm up by the fireplace, or cook! We are located in the Sullivan County Catskill region, next to the Hudson Valley and Delaware River regions. With farmland and hiking nearby, we know you will love this beautiful area.

Guest favorite

Guesthouse in Loch Sheldrake

4.96 out of 5 average rating, 27 reviews

Magical Catskills Escape w/ Pool & Private Lakes!

One-of-a-kind magic in the Catskills at “Casa del Monte” — a secluded, luxuriously appointed living space on 10 manicured acres of private land and water. Lake swimming, kayaking, paddleboarding and fishing on property! 5-minute walk from Loch Sheldrake lake and 15-25 minutes’ drive from the area's finest hiking, F&B, and entertainment — including Livingston Manor, Mountaindale, Callicoon, Roscoe, Beaverkill River, Willowemoc, Napanoch, White Lake, and Bethel Woods. 45 minutes from Woodstock.

Guest favorite

Home in North Branch

4.91 out of 5 average rating, 85 reviews

Indoor Heated Pool + Sauna + Creek, Spacious 4Bdrm

This one-of-a-kind property nestled in the quiet village of North Branch has all the makings of a dream vacation. This cozy home in the woods has 3 stunning acres with creek access towards the end of the property! Enjoy a full-size heated indoor pool + an infrared sauna open year-round combined with breathtaking scenery. If you're looking for a vacation for kids + adults, this peaceful home is for you! Enjoy a relaxing vacation in a comfortable home with all the beauty that nature has to offer.

Superhost

Cabin in Swan Lake

4.82 out of 5 average rating, 194 reviews

Stunning Sullivan County Cabin w/HotTub/Spa &Pool

This designer home is in the western Catskills, 2hrs away from NYC on 10 acres of hillside property. 20 mins from the Kartrite indoor water park. Perfect family getaway for hiking, canoeing, fishing , water sports. Quiet, secluded, fully stocked kitchen, 360 degree views , patio deck seating private heated pool from May 20- Sept 30 cabana, hammock, loungers Starting March 1st 2021, we are offering our newly installed Hot Tub/ Spa ( 5-6 seater) set into the side of hill w/ magnificent views

Guest favorite

Home in Monticello

4.9 out of 5 average rating, 10 reviews

Massive & Luxurious Catskills 6BR House

Come enjoy autumn in the Catskill Mountains! Fall is the best time to visit the Catskills. Crisp night, fresh apple cider, U-pick farms (ripe with apples, gourds, & pumpkins), bonfires, & picture-perfect fall foliage. Get outside to explore our local trails, parks & lakes, or visit the casino or indoor waterpark. You will feel right at home in this massive 6BR house. Located on a private 2.52 acre property near all the local hotspots & shopping, this is a great place for 4-season recreation.

Guest favorite

Home in Narrowsburg

5 out of 5 average rating, 16 reviews

Farm House Built in heated pool/over flow jacuzzi

Relax with the whole family at our peaceful home in the country. Enjoy the beautiful scenery that surrounds our home . In the summer months enjoy swimming in the pool or relax in the spa. In the pool area is an outdoor kitchen with a small refrigerator, propane grill , 24”griddle and a small sink . We have a nine hole pitch and putt coarse If you enjoy fishing, kayaking, boating, Lake Huntington is only 10 minutes away with a motorboat ramp or the Delaware River is only 15 minutes away .

Guest favorite

Cabin in Mongaup Valley

4.94 out of 5 average rating, 36 reviews

Amazing Retreat - Hot Tub, Arcade, 45 Acres!

Cozy, Pet Friendly Cabin w/Hot Tub, Barn & Arcade - 3 bed, 2 bath house with 2 Queen sized pull out couches - 3 level barn with arcade, pool and ping pong table, full bath, and loft area with 2 full sized beds -Together, the house and barn can sleep anywhere from 6 - 8 people - The property is 45 acres with plenty of natural forest to roam. - 6 person hot tub - 10-15 minute drive to multiple lakes, hiking, skiing, the Bethel Woods concert venue and other attractions - $200 Pet Fee

Superhost

Home in White Lake

4.93 out of 5 average rating, 42 reviews

Spacious, Cozy Catskills Getaway with Hot Tub

Beautiful four-bedroom renovated farmhouse two hours north of NYC. Modern amenities, including a hot tub and fully equipped kitchen, among five acres of wilderness. Great for families: Kids can enjoy toys and a playground. Nearby: lakes, spas, distilleries, skiing, casino, water park and great restaurants (see guidebook). Minutes from Bethel Woods, a world-class concert venue and the site of the 1969 Woodstock Festival. The charm of a country getaway in easy proximity to the city.

Guest favorite

Home in Narrowsburg

4.9 out of 5 average rating, 20 reviews

Catskills Retreat | Hot Tub & Fall Foliage

Just minutes away from Bethel Woods and the Delaware River our Narrowsburg escape combines airy space with style and luxurious comfort. Less than 2 hours from NYC, this family-friendly retreat is perfect for relaxation. Enjoy the manicured gardens, heated pool (in the summer), hot tub, and outdoor kitchen. The lower floor offers games and lounge space. Wander through the gardens and spend memorable nights by the fire pit under the stars—a magical space made for creating memories.

Guest favorite

Home in Liberty

5 out of 5 average rating, 11 reviews

*NEW* Catskills Indoor Pool House

Escape to the Catskills and enjoy private indoor pool all year long. Completely renovated and uniquely styled. Situated with beautiful golf course views from one side, pond views from the large back deck, and conveniently located right next to a store that you can walk to next door on a paved path if you forgot anything. Home is equipped with the basics as well as plenty to keep everyone busy such as a professional sized card table, vintage arcade game and TV for movie nights.

Superhost

Cabin in Eldred

4.94 out of 5 average rating, 196 reviews

Quiet Modern Cabin in the Woods w Hot Tub

This 3 acre hidden gem is tucked away in the woods of the Catskills. It's a wonderful getaway from the city or any bustling lifestyle. The outdoor fire pit and hot tub are both the perfect settings for serenity. When you come up here you can enjoy hiking, cooking, swimming or simply lounging & listening to our record collection and watching nature exist around you. Our house is about 20 minutes from Big Bear mountain which is a great (small) mountain for skiing and tubing.