
Holiday rentals with a pool in Catskill
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Catskill
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.

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.

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 +)

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.

Design Farmhouse w/ Pool + Firepit | Hudson Valley
A private, design-forward escape in Accord. One of the Hudson Valley’s most sought-after locations. BoHo Farm House is a luxe 3BR/3BA on 8 acres with a large dog-friendly fenced area. Recently renovated and featured in PureWow, the home offers vaulted ceilings, a light-filled open living space, chef’s kitchen, cozy fireplace, fire pits, and spa-like baths. Minutes from Inness, Westwind Orchard, Arrowood, and Stone Ridge, with easy access to hiking, skiing, and top farm-to-table dining. ⸻

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.

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!

Country Cottage w/ HOT TUB & Views
Welcome to the most peaceful and tranquil place in the world. Our beautiful home is situated on 3 acres of private land with a private pond and incredible views of the mountains. Escape your life and stressors, and come stay in the fresh air where all you will hear are birds chirping - no sirens, cars or people. The cottage is fully stocked to be enjoyed for all 4 seasons! Relax in the hot tub, or go for a swim in the pond. Our property is the perfect vacation getaway.

Luxe Retreat+Sauna+HotTub & Swimming on 12 acres
At the end of a dead end road on 12 acres, you'll find the perfect retreat. Highlights include a natural swimming pool, yoga deck, outdoor Japanese hot tub and sauna. Chef's kitchen, grill and smoker. Living room has a piano and seats a large group. Outside there's a 3 level stone patio, deck and firepit w/outdoor sound system. Private yoga & in-home massage. Peloton bike, Temperpedic & saatva mattress, beautiful linens! *extra 6 guests w/rental of guest house!

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.
Popular amenities for Catskill rentals with a pool
House rentals with a pool

Woodstock Family Home w/ Tree House + Heated Pool

Entire Home (private pool), Event Friendly

Hudson Getaway w/ Hot Tub + Fireplace on 20 Acres

Gorgeous Villa MntnViews, POOL, hot tub, grill!

MODERN FARMHOUSE in the WOODS

Woodstock Getaway - Heated Pool/Hot Tub/FirePit

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Upstate Modern Scandinavian Barn in the Catskills
Apartment rentals with a pool

Cozy Gem with Mountain Views

Windham Condo

One bedroom condo at Mountain Creek Resort

Appalachian Lodge Top Floor w/views

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

Resort Getaway @ Mtn. Creek -pool/hot tub/sauna

Lodge style getaway 50 miles from NYC patio 207
Home rentals with a private pool
Magnificent Hudson River Estate with Infinity Pool and Spa

Rhinebeck Country Living with a Modern Twist
Fenced & Salt Water Pool | Cozy Catskills Cottage
Catskills Winter Ski Retreat – Near Belleayre!
Quick stats about holiday rentals with a pool in Catskill

Total holiday rentals
Explore 10 holiday rentals in Catskill

Nightly prices starting at
Catskill holiday rentals start at $90 SGD per night before taxes and fees

Verified guest reviews
Over 1,410 verified reviews to help you choose

Wifi availability
10 of Catskill holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Catskill rentals

4.9 Average rating
Catskill stays are highly rated by guests – averaging 4.9 out of 5!
Destinations to explore
- Plainview Holiday rentals
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- Rentals with a washing machine and dryer Catskill
- Cabin rentals Catskill
- Ski-in/ski-out rentals Catskill
- Rentals with a patio Catskill
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- Pet-friendly rentals Catskill
- Flat rentals Catskill
- Rentals with a firepit Catskill
- Family-friendly rentals Catskill
- Cottage rentals Catskill
- Rentals with pools Greene County
- Rentals with pools New York
- Rentals with pools United States
- Hunter Mountain
- Belleayre Mountain Ski Center
- Jiminy Peak Mountain Resort
- Minnewaska State Park Preserve
- Catamount Mountain Ski Resort
- Windham Mountain
- Howe Caverns
- Thacher State Park
- Butternut Ski Area and Tubing Center
- Hunter Mountain Resort
- Plattekill Mountain
- Bash Bish Falls State Park
- Kent Falls State Park
- Bousquet Mountain Ski Area
- Zoom Flume
- Mohawk Mountain Ski Area
- Taconic State Park
- Norman Rockwell Museum
- Opus 40
- June Farms
- Naumkeag
- Benmarl Winery
- Berkshire Botanical Garden
- Millbrook Vineyards & Winery




