
Vacation rentals with a pool in Catskill Mountains
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Catskill Mountains
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

4Br Mountain Brook House on 130 acres w/ trails
Hemlock House is an extraordinary private escape nestled against a babbling brook running through the rocky gorge of an 130 acre magical historic farm. Explore hiking trails through old forests, trout creeks, and 90ft waterfall or simply relax by the fire pit or within the outdoor spa while listening to the flowing water. Visit this beautifully designed retreat, complete with gourmet kitchen, cozy fireplace, great wifi and comfortable bedrooms with quiet workspaces- learn more at cascadafarm.com

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.

Catskills Modernist Cabin Pool Hot Tub
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

Mtn View Lux Dome w/ Heated Plunge Pool
This luxury dome is a modern home perched on a mountain top. Our aim is to combine the comforts of a large hotel suite with all the healing qualities of nature. Venture out or hike our own trails leading to a pond and a stream in the woods. Suited for long term WFH stays! We have Fiberoptic internet (ethernet avail) and plenty of space for your setup. Stroll the property at lunch or jump in the heated plunge pool between calls. Ask me about a special offer for long term stays. (14 days +)

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!

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..

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.

Secluded Woodstock Retreat -Heated Pool and Sauna
Stunning, tranquil mountainside retreat with exposed beams, heated saltwater swimming pool, sauna, fireplace, soaking tub and rain shower. Situated on a 5-acre wooded hilltop, a ten minute drive to Woodstock and close to miles of walking trails. Roast marshmallows on the fire pit, flip burgers on the charcoal grill, and enjoy one of the best stargazing spots around. Indoors, find a well equipped kitchen and cinema sized tv screen with Netflix/Apple TV. Convenient to ski slopes.

Hudson River Sunset Getaway
With sunset views of the Hudson River and Catskill Mountains you can relax poolside during the summer months or enjoy the changing fall colors next to a cozy back yard bonfire in the fall. Located only 5 mins to downtown Hudson where you’ll find ample dining, drinking & shopping opportunities. Or head out to explore the Catskill Mountain Range only 30 mins away for the best hiking and skiing in the area. Sunset House is the perfect place for families or a couples getaway!

Spacious Catskills Farmhouse on over 5 acres!
Spring into fun in the Catskill Mountains! Our outdoor pool will open Memorial Day weekend! Enjoy a hike at one of our local trails or nature preserves. Try your luck at the casino, spend a day at the indoor water park, or play a round of golf at one of the local courses. You will feel right at home in this charming & restored 5BR farmhouse. Located on 5+ acres near the great Catskills Forest Preserve, this is a great place for four-season recreation.

Only Ski In Out on Mtn | Hike, Golf, Fish, Relax
Mountainside 1 bedroom cabin that fits 4! Ski on/off Hunter Mountain right from your doorstep. Enjoy hiking within a 5-minute drive or walk right onto the mountain from your porch. Unbeatable location on Hunter Mountain, short drive to the picturesque, colorful village of Tannersville, majestic Kaaterskill Falls, and renowned fishing! Fully stocked kitchen/bathroom, full entertainment system with streaming, high-speed WiFi, and dedicated work space.

Hike & Sauna! Modern Mountain Escape
Welcome to a brand new Catskills getaway. Inspired by Japanese and Scandinavian design, every detail has been thought through to create the perfect private retreat where interiors blend seamlessly with the surrounding mountains. You’ll see high end finishes throughout the space and all the amenities you could desire. Welcome to a relaxing stay at your home away from home.
Popular amenities for Catskill Mountains rentals with a pool
House rentals with a pool

Entire Home (private pool), Event Friendly

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Scenic River View Escape | New Paltz

Modern Barn on 12 acres w Sauna, FirePit+swimming

MODERN FARMHOUSE in the WOODS

Golf Sim! Hot Tub/Game Room/Cinema 2 Kings

Sunbeam Lodge: Pool+Sauna, 50 Acres, ‘70s Oasis

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Condo rentals with a pool

Cozy Gem with Mountain Views

Luxury. 5-Star. Ski In/Out, Heated Pool, Hot Tub

Windham Condo

Hideaway Windham/Hunter Fireplace, Snow & Skiing

Luxury 3-bedroom Condo on Windham mountain

4 Bedroom Condo, Close to Golf Courses and Biking

Windham Mountain Ski In Ski Out - Pool Hot Tub Gym

Cozy Mountain Condo
Other vacation rentals with a pool

Dino's Black Bear Cabin

Kapitans Cottage Heated Salt POOL Upstate Kingston

Catskill Mountain View Home with Hot Tub

Spirit Cabin: Lakefront w/Pool-Sauna-Cold Plunge

Thorne Hollow - Mountain Getaway with Pool+HotTub

Cheerful 3-bedroom Cabin in the Woods with a pool.

Cold Brook Cottage

Luxury Catskills Retreat with Heated Pool & Sauna
Destinations to explore
- Plainview Vacation rentals
- New York City Vacation rentals
- Tuckahoe Vacation rentals
- Long Island Vacation rentals
- Greater Toronto and Hamilton Area Vacation rentals
- Greater Toronto Area Vacation rentals
- Boston Vacation rentals
- Washington Vacation rentals
- East River Vacation rentals
- Mississauga Vacation rentals
- Hudson Valley Vacation rentals
- Jersey Shore Vacation rentals
- Cabin rentals Catskill Mountains
- Family-friendly rentals Catskill Mountains
- Cottage rentals Catskill Mountains
- House rentals Catskill Mountains
- Ski-in/ski-out rentals Catskill Mountains
- Lake house rentals Catskill Mountains
- Condo rentals Catskill Mountains
- Villa rentals Catskill Mountains
- Pet-friendly rentals Catskill Mountains
- Rentals with pools United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Bethel Woods Center for the Arts
- Minnewaska State Park Preserve
- Resorts World Catskills
- Catamount Mountain Ski Resort
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Bash Bish Falls State Park
- Plattekill Mountain
- Brotherhood, America's Oldest Winery
- Hunter Mountain Resort
- Taconic State Park
- Zoom Flume
- Storm King Art Center
- Opus 40
- Walkway Over the Hudson State Historic Park
- Benmarl Winery
- Millbrook Vineyards & Winery
- Woodloch Resort
- Warwick Valley Winery & Distillery
- Poets' Walk Park
- Peekamoose Blue Hole





