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.

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Guest favourite

Cabin in Livingston Manor

4.97 out of 5 average rating, 271 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 favourite

Home in Woodstock

4.99 out of 5 average rating, 237 reviews

The Woodstock Barn House - Sauna, Gym, Jacuzzi

19th Cent Hand-Hewn Dairy Barn. LOVE BIG GROUPS - if your #s exceed 10 we can accommodate. Pet Friendly Inquire for summer dates! IG: @woodstockbarnhouse 2 guest 1 night stays inquire for clean discount Travel & Leisure "Gorgeous Old Catskill Barn" House Beautiful "Best Upstate New York Weekend Destinations " Pool about May to midOct Hot Tub - all year Gym Sauna Fire Pit Projector Tv Pizza Ovens Cabana Kitchen 2 miles from center of town. *No checkin avail Tgiving, Xmas Day, Easter Sunday

Guest favourite

Townhouse in Hunter

4.9 out of 5 average rating, 127 reviews

Gorgeous Mountain View | Ski/Fast Wi-Fi/Wood Stove

Welcome to your amazing Catskills retreat in Hunter, NY! Marvel at the prime location with spectacular views situated only a 5 minute drive to Hunter Ski Mountain. Near hiking trails, waterfalls, antique shops and excellent restaurants. * 2 mins to Hunter North * 5 mins to Hunter base lodge * 13 mins to Windham * 15 mins to Colgate lake While at home enjoy views of the mountain on our deck - bask in the sun or grill a rack of ribs during the day or enjoy a glass of wine and stargaze at night.

Guest favourite

Apartment in Windham

4.88 out of 5 average rating, 155 reviews

Cozy Mountain hideaway Windham, Hunter

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.

Guest favourite

Home in Woodstock

4.92 out of 5 average rating, 228 reviews

Japanese Teahouse & Onsen, outside shower, tennis

Pool is open! Secluded country estate, a short drive to Woodstock, this Japanese teahouse is the ideal combination of away-from-it-all and convenience. The backyard is designed to make the most of the outdoors. Whether you’re here when the trees are turning golden brown in autumn, or when the sun shines in summer, there’s a spot outside for you. Sunny months see barbecues by the fire pit beneath, the stringed lights and swimm in the salt pool, play a game of tennis or bball and chill.

Guest favourite

Home in Woodstock

4.98 out of 5 average rating, 112 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..

Guest favourite

Chalet in Olivebridge

4.99 out of 5 average rating, 135 reviews

Spruced Moose Lodge & Treehouse w. Hot Tub & Pool!

Secluded log home on 5 acres, beautifully situated at the top of a no outlet road on a mountainside in the Catskills. The home has 4 bedrooms + 3.5 baths, with the 4th bedroom being a finished basement that has built-in full size bunk beds. There is also a sunroom, screened porch, pool, hot tub, and a treehouse that resembles a floating pirate ship 30 feet up in the trees, oh, and now a Projector TV in the basement! Town of Olive Registration No: STR-23-2 SEC-BLK-LOT: 52.4-1-5.500

Superhost

Cabin in South Kortright

4.91 out of 5 average rating, 190 reviews

Contemporary Cabin w/ Hot Tub, Lake & Fireplace

Ticking all the boxes, this cute 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.

Guest favourite

Home in Kerhonkson

4.95 out of 5 average rating, 339 reviews

Country House: Rustic Charm With Modern Feel

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favourite

Cabin in Shandaken

4.94 out of 5 average rating, 158 reviews

Private 4 Acre Retreat: Heated Pool + Hot Tub

Newly 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. *Fully private* (small houses are sheds) A ton of outdoor space to enjoy in addition to our fully private seasonal pool (Late May-mid Sept). Our newly added 6 person hot tub is available year round. It's the perfect spot for a much needed recharge with family and friends.

Guest favourite

Barn in Hillsdale

4.97 out of 5 average rating, 128 reviews

Hudson Valley Hilltop Barn

A private hilltop oasis in nature. Newly renovated barn with some luxury amenities including sauna & outdoor firepit & movie theater screen & hot tub* on a 15-acre hilltop w/ views & privacy in Hudson Valley / Berkshires. Walking trail around our hill. Fully stocked for cooking & tons of games. 100 acres of untouched nature around property. Near great shops & restaurants in Hudson & Great Barrington. Get private massages or yoga classes right at the house. *small extra fee

Guest favourite

Rental unit in Brookfield

4.94 out of 5 average rating, 216 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Welcome to our cozy apartment! This fully enclosed apartment is attached to our main house on a beautiful 3.5-acre property in Brookfield. Enjoy a kitchen, comfortable living and bedroom area, and a clean bathroom. Guests have access to a shared 32 ft, 10 ft deep pool, artist studio, pool table,, garden, fire space, and outdoor seating. We provide a guidebook for your convenience. Book now and experience a perfect blend of comfort, creativity, and relaxation.