Vacation rentals with a pool in Windham

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Windham

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

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Guest favorite

Home in Woodstock

4.99 out of 5 average rating, 247 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 favorite

Townhouse in Hunter

4.91 out of 5 average rating, 150 reviews

Peak Foliage - Stay at THE Ideal Hunter Home

FALL FOLIAGE GETAWAY -Classic Townhome- w/ Classic Feel. Centrally located spacious getaway with simple contemporary style w/ classic comfort and amazing views owned and operated by AIRBNB Super Host and NY Native. 2 min drive or 15 min walk to Hunter Mtn. Next to the boutique Scribner Lodge and their amazing restaurant. Hiking, biking, BBQ & breathe in the views and enjoy 2 stone fireplaces OR the outdoor fire pit Bedroom A/C's. Great for a family getaway or few days out of town w/ friends.

Guest favorite

Townhouse in Hunter

4.87 out of 5 average rating, 133 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 favorite

Condo in East Jewett

4.96 out of 5 average rating, 107 reviews

MountainViewSunny2BROutdoorGrillDeck

Escape to our sunlit two-bedroom Catskills condo, featuring a spacious deck with panoramic mountain views—perfect for morning coffee or stargazing. Embrace nature's tranquility by day, and cozy up by the fireplace for a magical mountain retreat under the stars. Conveniently located to towns of Windham and Tannersvile, lakes and hiking trails, 15-minute drive to Kaaterskill Falls. Rain or shine it’s a perfect place to recharge or get some work done with super amazing views and sounds of nature.

Guest favorite

Townhouse in Windham

4.9 out of 5 average rating, 136 reviews

Amazing + pet friendly gem in the heart of Windham

Amazing 2 floor spacious getaway with A/C just minutes away from Windham Mountain ski resort, hiking trails, and great restaurants. Family friendly home with a large inviting living room, 2 spacious bedrooms, 2 full bathrooms and wood burning fireplace. Updated kitchen appliances, super-fast Wi-Fi and 3 smart TV's. Many extras including parking, 2 tennis courts, swimming pool and firepit. BBQ Grill on private back deck with scenic views. Winter season rentals preferred during Dec - March.

Guest favorite

Dome in Hobart

4.93 out of 5 average rating, 109 reviews

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 +)

Guest favorite

Condo in Windham

4.88 out of 5 average rating, 163 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.

Superhost

Townhouse in Windham

4.83 out of 5 average rating, 188 reviews

Redwood Retreat in Windham - Pickleball! Tennis!

True mountain getaway, just 2.5 hours from NYC!! Spacious 2 bedroom 2 bathroom townhouse minutes to Windham Mountain. Enjoy beautiful wood-burning fireplace, Roku TV and high speed Wi-Fi perfect for remote work. Amenities include outdoor pool (open from Memorial through Labor Day), pickleball, basketball and tennis courts, as well as a fire pit with Adirondack chairs. Very close to town and the amazing escarpment hiking and Elm Ridge mountain bike trails. NOW OPEN FOR 2024/25 SKI SEASON!!

Guest favorite

Cabin in Prattsville

4.82 out of 5 average rating, 163 reviews

Private 6 acre w/Mountain Views; POND & HOT TUB!

Welcoming you to the beautiful Catskills with our renovated (May 22') Modern Cabin with a Private SWIM POND situated on 6 acres w/ lovely and expansive mountain views and backed to 240 acres of NYC DEP LAND FOR HIKING, HUNTING & MORE!! The House is fully stocked to be enjoyed for all seasons! Take a dip, boat, fish or ice skate on the POND. Relax in the HOT TUB or lounge in the HAMMOCK or ADIRONDACK Chairs around the FIRE PIT while enjoying the views!! Enjoy grilling on the GAS GRILL!!

Guest favorite

Home in Woodstock

4.98 out of 5 average rating, 120 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 favorite

Cabin in Shandaken

4.95 out of 5 average rating, 164 reviews

Cozy Catskills 4Br Retreat w/ FirePit & Hot Tub

7 min drive to Phoenicia 10 min drive to Belleayre Mountain 25 min drive to Hunter Mountain 35 min drive to Windham Mountain 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-mid Sept). Our newly added 6 person hot tub is available year round.

Superhost

Cottage in Denver

4.97 out of 5 average rating, 122 reviews

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.