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

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

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

฿3,340

฿4,188 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

2. Wylder Hotel Windham

Windham

Outdoor pool

฿8,978

฿11,372 total

includes taxes & fees

29 Oct - 30 Oct

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

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

3. The Winwood Condominiums

Windham

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

฿5,602

฿6,050 total

includes taxes & fees

14 Oct - 15 Oct

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

A modern breakfast area with a coffee machine, cereal, and bakery options.

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

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

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

Saugerties

Indoor pool

฿4,271

฿4,784 total

includes taxes & fees

11 Nov - 12 Nov

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

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.

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

5. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Outdoor pool
2 hot tubs

฿5,997

฿7,141 total

includes taxes & fees

11 Nov - 12 Nov

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".

6. The Colonial Motel

Grand Gorge

Pool loungers

฿2,988

฿3,286 total

includes taxes & fees

21 Oct - 22 Oct

A swimming pool with lounge chairs and umbrellas.

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

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.

7. Crystal Brook Resort & Mountain Brauhaus

Round Top

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

฿7,332

฿7,918 total

includes taxes & fees

30 Oct - 31 Oct

A swimming pool with lounge chairs and potted plants.

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

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

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

8. Moore's Motel

Prattsville

Outdoor pool

฿4,024

฿4,345 total

includes taxes & fees

19 Oct - 20 Oct

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

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

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.

9. Shandaken Inn

Shandaken

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

฿4,782

฿5,357 total

includes taxes & fees

28 Oct - 29 Oct

A modern dining area with wooden tables and benches, green chairs, and pendant lighting.

A compact living space with a kitchenette, a flat-screen TV, and a seating area.

A hotel lobby with orange rocking chairs, a reception desk, and a green carpet.

A hotel room with a wooden desk, a television, a grey office chair, a sofa, and a window with curtains.

10. Spark by Hilton West Coxsackie

West Coxsackie

Indoor pool

฿3,974

฿4,292 total

includes taxes & fees

1 Nov - 2 Nov

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 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, desk, chair, TV, and kitchenette.

11. Comfort Inn Saugerties

Saugerties

Indoor pool

฿4,813

฿5,390 total

includes taxes & fees

1 Nov - 2 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 picnic table, playground equipment, and a swimming pool within a fenced area.

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

12. Four Seasons Motel

Catskill

Pool
Free parking
Free Wi-Fi
Air-conditioning

฿3,353

฿3,621 total

includes taxes & fees

26 Oct - 27 Oct

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

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.

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

13. Howard Johnson by Wyndham Saugerties

Saugerties

Indoor pool

฿3,693

฿4,136 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

14. The Graham & Co.

Phoenicia

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

฿5,253

฿5,884 total

includes taxes & fees

2 Nov - 3 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.

15. Red Ranch Motel

Catskill

Pool loungers

฿3,581

฿3,867 total

includes taxes & fees

1 Nov - 2 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 couple standing on a wooden deck overlooking a landscaped garden with a river view.

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

16. Emerson Resort & Spa

Mount Tremper

Pool umbrellas
Hot tub

฿6,002

฿6,722 total

includes taxes & fees

1 Nov - 2 Nov

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

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

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

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

17. Eastwind Oliverea Valley

Big Indian

Outdoor pool
Pool loungers

฿8,950

฿11,655 total

includes taxes & fees

20 Oct - 21 Oct

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

A kitchen with a stove, kettle, toaster, and utensils on the counter.

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.

18. Catskill Seasons Inn

Shandaken

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

฿5,415

฿6,065 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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