A canoe on a calm lake with a forested shoreline.

Hotels with a Pool in Windham

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Hotels with a Pool in Windham

Properties are selected based on real traveller 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 traveller experience. Last updated on 22 September 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 cabin with a deck, large windows, and a mountain backdrop.

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

A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

1. Hotel Vienna

Windham

Indoor pool

HK$779

HK$977 total

includes taxes & fees

1 Oct - 2 Oct

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

A compact living space with a kitchen, dining area, and seating.

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.

2. The Winwood Condominiums

Windham

Pool
Free parking
Free Wi-Fi
Gym
Laundry facilities
Child-friendly activities

HK$1,171

HK$1,265 total

includes taxes & fees

28 Sept - 29 Sept

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

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

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

HK$2,002

HK$2,555 total

includes taxes & fees

24 Sept - 25 Sept

A swimming pool with lounge chairs and potted plants.

A hotel room with two beds, a desk, a chair, and a TV on a stand.

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

HK$941

HK$1,017 total

includes taxes & fees

23 Sept - 24 Sept

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

A covered porch with outdoor seating, a staircase, and potted plants.

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

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".

5. The Colonial Motel

Grand Gorge

Pool loungers

HK$699

HK$769 total

includes taxes & fees

23 Sept - 24 Sept

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

A cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.

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

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

6. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Outdoor pool
2 hot tubs

HK$1,550

HK$1,846 total

includes taxes & fees

29 Sept - 30 Sept

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 compact kitchen with wooden cabinets, a refrigerator, a sink, and a dining area with a table and chairs.

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

7. Red Ranch Motel

Catskill

Pool loungers

HK$1,008

HK$1,089 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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

8. Four Seasons Motel

Catskill

Pool
Free parking
Free Wi-Fi
Air-conditioning

HK$784

HK$847 total

includes taxes & fees

27 Sept - 28 Sept

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

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

A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.

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

9. Howard Johnson by Wyndham Saugerties

Saugerties

Indoor pool

HK$1,090

HK$1,221 total

includes taxes & fees

5 Oct - 6 Oct

A swimming pool with lounge chairs and umbrellas.

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.

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

10. Crystal Brook Resort & Mountain Brauhaus

Round Top

Pool
Free breakfast
Free parking
Free Wi-Fi
Restaurant
Air-conditioning

HK$1,710

HK$1,847 total

includes taxes & fees

27 Sept - 28 Sept

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

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

A corridor with white walls, wooden slats, and a concrete floor.

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

11. The Graham & Co.

Phoenicia

Pool
Pet-friendly
Free parking
Free Wi-Fi
Air-conditioning
Non-smoking

HK$1,338

HK$1,498 total

includes taxes & fees

23 Sept - 24 Sept

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

A bedroom with a bed, two bedside tables, a chair, a small table, and a window.

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

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 Wi-Fi
Air-conditioning
Non-smoking

HK$1,255

HK$1,406 total

includes taxes & fees

23 Sept - 24 Sept

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

A reception area with a wooden reception desk, a television mounted on the wall, a blue sofa, and a fireplace with plants.

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

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

13. Comfort Inn Saugerties

Saugerties

Indoor pool

HK$1,260

HK$1,411 total

includes taxes & fees

27 Sept - 28 Sept

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

A spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

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

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

HK$1,691

HK$1,894 total

includes taxes & fees

29 Sept - 30 Sept

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 stone building with a chimney, a pool, and a sign for Shandaken Inn.

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

15. Shandaken Inn

Shandaken

Pool
Free breakfast
Pet-friendly
Free parking
Free Wi-Fi
Gym

HK$1,589

HK$1,779 total

includes taxes & fees

1 Oct - 2 Oct

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

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

A triangular wooden tent with a bed inside, featuring a view of a forest with yellow foliage.

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

16. Eastwind Oliverea Valley

Big Indian

Outdoor pool
Pool loungers

HK$1,980

HK$2,594 total

includes taxes & fees

4 Oct - 5 Oct

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Discover your perfect hotel with a pool in Windham

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Hot tub

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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 practise 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)

Travellers might want a tour of Windham Vineyards and Winery, just one of the places to visit, 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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About the destination

Windham is a relaxing city where you can spend time checking out the its coffee shops. If you're visiting during colder months, enjoy activities such as skiing during your stay. Plan a fun excursion to Windham Country Club and Windham Vineyards and Winery while here. There's plenty more to see, including sights like Windham Mountain Resort and Catskill State Park.

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