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

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

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

1. Hotel Vienna

Windham

Indoor pool

HK$821

HK$1,022 total

includes taxes & fees

10 Nov - 11 Nov

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

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

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

2. The Winwood Condominiums

Windham

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

HK$1,326

HK$1,432 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

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

3. Wylder Hotel Windham

Windham

Outdoor pool

HK$1,501

HK$2,013 total

includes taxes & fees

29 Oct - 30 Oct

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

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

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

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

4. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Outdoor pool
2 hot tubs

HK$1,399

HK$1,666 total

includes taxes & fees

12 Nov - 13 Nov

A swimming pool with clear water, surrounded by walls with emergency contact information and pool rules.

A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

A modern lobby with a reception desk, seating area, and a dining section.

5. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Saugerties

Indoor pool

HK$997

HK$1,116 total

includes taxes & fees

11 Nov - 12 Nov

A swimming pool with lounge chairs and umbrellas.

A sign for Crystal Brook Resort surrounded by red tulips.

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

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

6. Crystal Brook Resort & Mountain Brauhaus

Round Top

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

HK$1,711

HK$1,848 total

includes taxes & fees

30 Oct - 31 Oct

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

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.

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

7. The Colonial Motel

Grand Gorge

Pool loungers

HK$657

HK$723 total

includes taxes & fees

18 Oct - 19 Oct

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

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

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

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

8. Shandaken Inn

Shandaken

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

HK$1,116

HK$1,250 total

includes taxes & fees

27 Oct - 28 Oct

A swimming pool with lounge chairs and potted plants.

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

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

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

9. Moore's Motel

Prattsville

Outdoor pool

HK$942

HK$1,017 total

includes taxes & fees

16 Oct - 17 Oct

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, desk, chair, TV, and kitchenette.

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

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

10. Comfort Inn Saugerties

Saugerties

Indoor pool

HK$1,123

HK$1,258 total

includes taxes & fees

1 Nov - 2 Nov

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

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.

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

11. The Graham & Co.

Phoenicia

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

HK$1,226

HK$1,373 total

includes taxes & fees

3 Nov - 4 Nov

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

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

12. Four Seasons Motel

Catskill

Pool
Free parking
Free Wi-Fi
Air-conditioning

HK$785

HK$848 total

includes taxes & fees

15 Oct - 16 Oct

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

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

13. Howard Johnson by Wyndham Saugerties

Saugerties

Indoor pool

HK$862

HK$965 total

includes taxes & fees

2 Nov - 3 Nov

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

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

14. Eastwind Oliverea Valley

Big Indian

Outdoor pool
Pool loungers

HK$2,026

HK$2,647 total

includes taxes & fees

2 Nov - 3 Nov

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 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.

15. Emerson Resort & Spa

Mount Tremper

Pool umbrellas
Hot tub

HK$1,349

HK$1,510 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

16. Red Ranch Motel

Catskill

Pool loungers

HK$838

HK$905 total

includes taxes & fees

1 Nov - 2 Nov

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

A building facade with a dark exterior, a window with blinds, a small porch with a railing, and flower planters on the porch.

A bathroom with a toilet, a bathtub, and a shower.

A hotel room with two single beds, a nightstand with a lamp, and a dark blue accent wall.

17. Catskill Seasons Inn

Shandaken

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

HK$1,263

HK$1,415 total

includes taxes & fees

19 Oct - 20 Oct

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Discover your perfect hotel with a pool in Windham

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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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