Holiday rentals with a pool in New York

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in New York

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
Chalet in Olivebridge
4.99 out of 5 average rating, 175 reviews

Spruced Moose Lodge & Treehouse w/ New Hot Tub!

**Dates blocked? Send us a message. We haven't opened most of our 2026 calendar yet & many days are actually available.** Secluded log home nestled in 5 acres of Catskill mountain forest, with 4 bedrooms & 3.5 baths (incl. basement with built-in full size bunks). Enjoy a sunroom, screened porch, pool+ brand new hot tub, projection screen home theater & 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

Top guest favourite
An aerial view of BoHo Farm House showcases a modern black exterior with expansive glass panels. The garden features a swimming pool surrounded by lounging chairs and a fire pit, set against a backdrop of lush green grass and trees.
Home in Accord
5 out of 5 average rating, 103 reviews

BoHo Scandi Farm Retreat, Fire, Pool, Dog Paradise

BoHo Farm House is a luxe, modern 3BR/3BA retreat on 8 stunning acres in Accord, Hudson Valley with a large fully-fenced area for dogs & kids to roam safely. Featured in PureWow, this newly renovated Scandi farm escape includes vaulted wood ceilings, large open living space and chef’s kitchen, cozy fireplace, fire pits, and spa-like ensuite bathrooms. Close to incredible hiking, skiing, and farm-to-table dining. 5 minutes from Inness, Westwind, Arrowood, and the towns of Stone Ridge & Kerhonkson

Top guest favourite
A bright, modern kitchen features white cabinetry and stainless-steel appliances, including a refrigerator and microwave. The dining area includes a small table with clear chairs and a potted plant, while natural light filters through two windows, highlighting the clean, airy design.
Guest suite in Hudson
4.99 out of 5 average rating, 117 reviews

Le Soleil Suite - Pool, Mtn Views Near Hudson

A charming one-bedroom suite in a rural neighborhood 10 minutes by car from downtown Hudson. Your rental is a private, independent unit next to the main house. It has a full kitchen, bathroom, electric fireplace and a private backyard with a grill, firepit and pool (June to Sept.). If we are around, we give you privacy. Watch sunset over the Catskills from the living room. 1 Br with queen bed, 1 pullout sofa, 1 fold-out twin upon request. Close to Hudson, hiking, skiing, Olana and Art Omi.

Top guest favourite
A modern cabin features a peaked roof and large glass windows, set amidst lush greenery. A heated pool is visible in the yard, surrounded by comfortable lounge chairs, inviting relaxation in a tranquil outdoor setting.
Cabin in Red Hook
4.96 out of 5 average rating, 378 reviews

Modern Upstate Cabin, near Rhinebeck NY

[ 🏊🏽‍♂️ Heated pool is open end of May - end of October. During the winter months we recommend soaking in our giant freestanding tub, which easily fits 2 humans.] Welcome to Maitopia - our modern, dog-friendly, tiny cabin in the middle of a forest. We offer a fully stocked kitchen, a giant bathtub, a floating fireplace and a heated pool in the summer. Plus, a fenced in yard for your pup to roam! Please note: Because of bad experiences we don’t accept bookings from guests without reviews.

Superhost
An indoor heated pool is featured within a cozy enclosure, surrounded by large windows showcasing tranquil winter scenery. A distinctive swan-shaped float rests on the water's surface, and comfortable seating is positioned nearby for relaxation.
Home in North Branch
4.89 out of 5 average rating, 151 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.

Top guest favourite
An aerial view captures the expansive landscape surrounding the barn, featuring vibrant autumn foliage and rolling mountains in the background. A serene pond is nestled among the trees, with the property’s expansive lawn visible in the foreground, emphasizing the natural beauty of the 12-acre site.
Home in Saugerties
5 out of 5 average rating, 163 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. The house 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.

Top guest favourite
Apartment in Windham
4.9 out of 5 average rating, 230 reviews

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Spacious 1BR condo for a max. of 4 guests , sleeps 2 in separate bedroom , additional 2 on an inflatable airbed . Balcony with mountain view ,2 tennis courts ,outdoor pool . Awesome location . Windham and Hunter within reach .Get close to nature in the nearby hiking trails, Windham Path, Kaaterskill Falls. Kayaking on North-South Lake or ziplining in Hunter,skiing ,snowboarding ,golfing and mountain biking . Leave your worries at home and come to relax.Enjoy many dining options in town.

Top guest favourite
An inviting hot tub is positioned on a wooden deck, overlooking a spacious backyard and the tastefully designed home. Soft lighting enhances the outdoor setting as sunset hues paint the sky, creating a serene atmosphere perfect for relaxation.
Cabin in Livingston Manor
4.97 out of 5 average rating, 337 reviews

Experience The Zen House

Enjoy your own private indoor movie theater with 7.1 Klipsch Premiere Surround Sound and leather recliner seats, a spa with a cold plunge pool & 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! Amenities Include: - Hot Tub - Bath House with Sauna & Cold Plunge Pool - 12 Person Theater with immersive visual & surround sound + recliners - Game Room - Outdoor Fire Pit - Hammock & much more!

Guest favourite
Cabin in Shandaken
4.95 out of 5 average rating, 229 reviews

4Br l Fire-pit l Hot Tub l 10 min to Belleayre

7 min drive to Phoenicia 10 min drive to Belleayre 25 min drive to Hunter 35 min drive to Windham Renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-Sept). 6 person hot tub is available year round. Not for parties!! Please be mindful of our neighbors!

Guest favourite
Home in Narrowsburg
4.94 out of 5 average rating, 227 reviews

6-Acre Lux Estate: Hot Tub, Fireplace, Near Skiing

A modern 3BR/2BA Catskills retreat on 6 private acres with a hot-tub, and fireplace. Perched on a hill, this single-level home offers serenity, scenic views, mid-century modern decor, and comfort—ideal for girls' trips, couples and families. Amenities: Fireplace Hot Tub Spa Mini Ping-Pong Dart Board High-speed Wi-Fi Narrowsburg Offers: -Restaurants & Shops -Luxury Spas & Yoga -Alpaca Farm -Hiking -Farmer's Markets -Delaware Valley Arts Alliance Experience the best of the Catskills!

Superhost
Cabin in South Kortright
4.89 out of 5 average rating, 278 reviews

Contemporary Cabin w/ Hot Tub, Lake & Fireplace

Ticking all the boxes, this beautiful cabin has everything you could want for your retreat from city life! Five acres of private forest encapsulates the perfect seasonal mood as you step from the great room onto the huge wrap-around deck. Relax and enjoy the property with its hot tub, fireplace, A/C, BBQ grill and poolside loungers. For the adventurous at heart, check out the community shared lake access (non fishing), rivers, hiking trails and ski stations right at your fingertips.

Top guest favourite
A cozy living space is highlighted by a light wooden floor and a white shiplap ceiling. A comfortable brown leather couch and an orange accent chair provide seating. A wooden coffee table sits in front of the sofa. Wall art and a floor lamp add warmth to the room.
Cottage in Kingston
4.93 out of 5 average rating, 405 reviews

Kapitan’s Cottage Private Winter Retreat Kingston

Escape the city to this cozy vintage rustic Catskills retreat—perfect for couples, families, and pet-friendly winter getaways. This 2BR, 1.5BA two-story home blends country charm with modern comforts, a large private yard, stone deck, fire pit, and BBQ. Close to skiing, hiking, parks, Kingston, Woodstock, and High Falls—yet secluded enough to truly unwind. Ideal for weekend or midweek escapes upstate. Pet-friendly, generator on-site. Inground salt pool open Mid May- Sept.

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