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 favourite

Townhouse in Hunter

4.9 out of 5 average rating, 115 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.

Jun. 20 – 27

$219 CAD per night

Guest favourite

Townhouse in Windham

4.91 out of 5 average rating, 111 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.

Apr. 3 – 10

$248 CAD per night

Guest favourite

Condo in Windham

4.89 out of 5 average rating, 133 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.

Jul. 3 – 10

$157 CAD per night

Guest favourite

Townhouse in Hunter

4.91 out of 5 average rating, 136 reviews

Spring into a Dynamic Stay at an Ideal Hunter Home

Classic Townhome- w/ Classic feel. SPRING SPECIALS Centrally located spacious getaway with simple contemporary style with classic comfort w/ amazing views owned and operated by AIRBNB Super Host and NY Native. 2 min drive or a 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.

May 6 – 13

$142 CAD per night

Guest favourite

Cabin in Shandaken

4.95 out of 5 average rating, 143 reviews

4br Catskills Retreat l Hot Tub & Fire Pit

Newly renovated 1920’s cabin style home nestled on 4 acres in the Catskill Mountains. Very easy to get to and conveniently located near great restaurants, skiing, hiking, tubing, fishing, and swimming holes. *Fully private* ( small houses pictured 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.

Jul. 2 – 9

$1,212 CAD per night

Guest favourite

Cabin in Prattsville

4.82 out of 5 average rating, 154 reviews

6 acre w/SWIM pond w/boats & floats plus 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!!

Oct. 17 – 24

$532 CAD per night

Guest favourite

Home in Woodstock

4.98 out of 5 average rating, 100 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..

Jan. 15 – 22

$1,191 CAD per night

Superhost

Townhouse in Windham

4.82 out of 5 average rating, 177 reviews

Redwood Retreat in Windham - minutes to Mtn!

True mountain getaway, just 2.5 hours from NYC!! Modern and clean 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. Complex amenities include outdoor pool (open from Memorial Day through Labor Day) 2 tennis courts and 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!!

Aug. 28 – Sep. 4

$332 CAD per night

Superhost

Cottage in Denver

4.96 out of 5 average rating, 110 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.

Jul. 8 – 15

$742 CAD per night

Guest favourite

Guesthouse in Margaretville

4.99 out of 5 average rating, 134 reviews

Sunny Arts & Crafts Loft

Catskill Mtn. Summer: hiking, swimming, relaxing. Explore fun towns like Margaretville, Andes & more. May & June are almost fully booked, but lots of great summer and fall dates available. Situated on a peaceful mountainside, the loft is a cozy, private place to unwind as you enjoy a Catskill Mtn. adventure. Super savings on longer stays, too! Our road is plowed & sanded, but you will definitely need AWD & good tires to ensure smooth travels in the WINTER months.

Nov. 1 – 8

$153 CAD per night

Guest favourite

Cabin in Saugerties

4.99 out of 5 average rating, 123 reviews

Lovely cabin by the stream

We are close to HITS, Hunter Mtn and all of the wonderful activities of the Hudson Valley. This is a very peaceful cabin, steps from the stream. We are perfect for single guests or a maximum of two people (including children) as the cabin is quite small. The cabin is private and set in the woods, yet steps away from the pool, sauna, screen house. We are a carbon neutral property, with a large solar array and a Level 2 EV charger.

Oct. 18 – 25

$229 CAD per night

Guest favourite

Guesthouse in Kingston

4.92 out of 5 average rating, 288 reviews

The Antique Stone House

A Private Guesthouse in the historic Antique Stone House built in 1810 is awaiting your visit. This Stone House offers a great location in the beautiful Historic City of Kingston, New York, (First Capital of New York State. ) located 90 miles north of Manhattan, for trips, adventures, and outings in every direction. Close to Stockade District and the Waterfront.

Sep. 28 – Oct. 5

$279 CAD per night