Hotels with a Pool in Windham

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Top 5 Hotels with a Pool in Windham at a glance

1. Hotel Vienna — 3-star hotel in Windham. Guest rating: 9.4/10 — Exceptional.
2. The Winwood Condominiums — 3-star hotel in Windham. Guest rating: 8.8/10 — Excellent.
3. Wylder Hotel Windham — 3.5-star hotel in Windham. Guest rating: 8.8/10 — Excellent.
4. Moore's Motel — 2.5-star hotel in Prattsville. Guest rating: 8.6/10 — Excellent.
5. The Colonial Motel — 2.5-star hotel in Grand Gorge. Guest rating: 9.6/10 — Exceptional.

Hotels with a Pool in Windham

Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Windham on Hotels.com. These Windham Hotels with a Pool consistently deliver on quality, location and traveler experience. Last updated on September 22, 2026.

A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.

A cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.

A cabin with a deck, large windows, and a mountain backdrop.

A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Windham

Indoor pool

CA $163

CA $200 total

includes taxes & fees

Oct 1 - Oct 2

A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

A two-story building with a balcony, surrounded by well-maintained lawns and trees.

A kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

2. The Winwood Condominiums

Windham

Pool
Free parking
Free WiFi
Gym
Laundry facilities
Child-friendly activities

CA $209

CA $226 total

includes taxes & fees

Sep 24 - Sep 25

A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

A modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.

Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.

3. Wylder Hotel Windham

Windham

Outdoor pool

CA $359

CA $458 total

includes taxes & fees

Sep 24 - Sep 25

A swimming pool with lounge chairs and potted plants.

A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.

A two-story motel with a central staircase, balconies, and a grassy front yard.

A two-story building with a large front porch, a chimney, and a balcony.

4. Moore's Motel

Prattsville

Outdoor pool

CA $168

CA $182 total

includes taxes & fees

Sep 27 - Sep 28

A swimming pool with a fenced deck, lounge chairs, and umbrellas.

A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

A cozy room with a white sofa, a wooden table with a lamp, and a chair with a patterned cushion. There's a reception desk with a computer and a sign that says "Welcome".

A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

5. The Colonial Motel

Grand Gorge

Pool loungers

CA $125

CA $138 total

includes taxes & fees

Sep 27 - Sep 28

A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

A cozy lounge area with leather sofas, a fireplace, and a large window overlooking a garden.

A multi-story building with outdoor seating and a stone-paved patio.

A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

6. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Outdoor pool
2 hot tubs

CA $278

CA $331 total

includes taxes & fees

Sep 24 - Sep 25

A swimming pool with lounge chairs and a red building in the background.

A cozy lobby with patterned sofas, a wooden reception desk, and a mirror reflecting the interior.

A storefront with a 'DEFACE' sign, a 'NO PETS' notice, and various seasonal decorations including pumpkins and flowers.

A hotel room with two beds, a wooden dresser, a television, and a stone wall.

7. Red Ranch Motel

Catskill

Pool loungers

CA $180

CA $195 total

includes taxes & fees

Sep 24 - Sep 25

A motel with a swimming pool, picnic tables, and a playground.

A motel with a single-story structure, a covered parking area, and a swing set in the yard.

A hotel room with two beds, a nightstand with a lamp, and a window with floral curtains.

A motel with a porch, a small stream, and parked vehicles.

8. Four Seasons Motel

Catskill

Pool
Free parking
Free WiFi
Air conditioning

CA $140

CA $152 total

includes taxes & fees

Sep 29 - Sep 30

An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

A hotel room with two beds, a TV, a dresser, and a door leading to another room.

A restaurant with a bar area, wooden booths, and a coffee machine.

A bathroom with a granite countertop sink, a large mirror, and a shower with a glass door.

9. Howard Johnson by Wyndham Saugerties

Saugerties

Indoor pool

CA $195

CA $218 total

includes taxes & fees

Sep 29 - Sep 30

A swimming pool with lounge chairs and umbrellas.

A buffet table with various food items and a painting on the wall.

A cozy living room with a plaid sofa, a fireplace, and various decorative items on shelves above the fireplace.

A wooden lodge with a welcoming sign, a bear statue, and two flags.

10. Crystal Brook Resort & Mountain Brauhaus

Round Top

Pool
Free breakfast
Free parking
Free WiFi
Restaurant
Air conditioning

CA $306

CA $330 total

includes taxes & fees

Sep 27 - Sep 28

A pool area with a wooden deck, benches, and umbrellas.

A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.

A campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.

11. The Graham & Co.

Phoenicia

Pool
Pet friendly
Free parking
Free WiFi
Air conditioning
Non-smoking

CA $239

CA $268 total

includes taxes & fees

Sep 29 - Sep 30

A dining area with a round wooden table and four chairs, a chandelier with lights, and a white door in the background.

A dark-colored house with a metal roof, surrounded by trees and a fenced area.

A compact kitchen with a central island, a microwave, a stove, a refrigerator, and a cabinet with glass doors.

A two-story building with a dark exterior, surrounded by a grassy area with picnic tables.

12. Catskill Seasons Inn

Shandaken

Pool
Pet friendly
Free parking
Free WiFi
Air conditioning
Non-smoking

CA $225

CA $251 total

includes taxes & fees

Sep 27 - Sep 28

An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.

A hotel room with a bed, a desk, a sofa, and two lamps.

A buffet area with various food items, a coffee machine, and a refrigerator.

A hotel room with a bed, desk, chair, TV, and kitchenette.

13. Comfort Inn Saugerties

Saugerties

Indoor pool

CA $225

CA $252 total

includes taxes & fees

Sep 27 - Sep 28

A log cabin with a tower, a swimming pool, and lounge chairs.

A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

A hallway with intricate carvings on the walls and a large vase in the center.

A couple standing on a wooden deck overlooking a landscaped garden with a river view.

14. Emerson Resort & Spa

Mount Tremper

Pool umbrellas
Hot tub

CA $303

CA $339 total

includes taxes & fees

Sep 27 - Sep 28

A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.

A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.

A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.

A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

15. Shandaken Inn

Shandaken

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Gym

CA $285

CA $319 total

includes taxes & fees

Oct 1 - Oct 2

A pool area with a wooden deck, benches, and a lifebuoy.

A wooden deck with two lounge chairs and a small table, overlooking a forested area.

A cozy dining area with wooden walls, large windows, and a central wood-burning stove. Tables are set with glasses and cutlery.

A modern building with a gravel driveway and a stack of firewood in the foreground.

16. Eastwind Oliverea Valley

Big Indian

Outdoor pool
Pool loungers

CA $366

CA $478 total

includes taxes & fees

Sep 29 - Sep 30

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Discover your perfect hotel with a pool in Windham

Breakfast included

Hot tub

4 stars

5 stars

Spa

Top landmarks in Windham

Windham Mountain Resort

9.0/10 (313 reviews)

Skiers and snowboarders might want to test out the slopes at Windham Mountain Resort, a skiing spot located 1.2 mi (1.9 km) from central Windham. If you master the slopes, Hunter Mountain and Mountain Trails Cross Country Ski and Snowshoe Center are also just a short drive away.

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Windham Country Club

8.4/10 (20 reviews)

You might want to practice your swing at Windham Country Club, a golf course located 1 mi (1.6 km) from central Windham.

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Windham Vineyards and Winery

9.0/10 (15 reviews)

Travelers might want a tour of Windham Vineyards and Winery, just one of the places to visit, and located 3.4 mi (5.4 km) from central Windham.

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Huntersfield State Forest

Huntersfield State Forest is 6.2 mi (9.9 km) from central Windham, why not stop by during your stay.

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Elm Ridge Wild Forest

Elm Ridge Wild Forest is 3.5 mi (5.7 km) from central Windham, why not stop by during your stay.

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Ashland Park

Ashland Park is 4.4 mi (7 km) from central Windham, why not stop by during your stay.

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Frequently asked questions

What are the best hotels with a pool in Windham?

One of the best Windham hotels with a pool based on guest reviews is Hotel Vienna. Make the most of an electric car charging station and mountain views here. Every day can also be a pool day at The Country Place Resort - Home of Zoom Flume Water Park, another traveller favourite.

What are the cheapest hotels with a pool in Windham?

Enjoy all the poolside perks without the splurge at Hotel Vienna. This property also offers a firepit and an electric car charging station. Check out the range of cheap hotels in Windham with a pool from CA $152 and live it up for less.

What is the best time to stay in a hotel with a pool in Windham?

If you'd like to visit when crowds are smaller, head here in April. You could snag some great deals on Windham hotels with a pool around that time. The warmest conditions are in July, with temperatures ranging from 14ºC to 26ºC. It's coolest in January, which has averages of between -9ºC and -3ºC.

Are there any hotels with a pool in Windham with parking?

You'll find 2,188 Windham hotels with a pool and parking. Pull up and go for a dip at Hotel Vienna. Mountain views and an electric car charging station are included in your stay too. Or, head to The Country Place Resort - Home of Zoom Flume Water Park, where you can easily access both parking and a pool.