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Hotels with a Pool in Windham

October 2026
1
November 2026

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Oct 2 - Oct 4
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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 October 1, 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 modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.
A cabin with a deck, large windows, and a mountain backdrop.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool
NT$3,759
NT$4,611 total
includes taxes & fees
Oct 4 - Oct 5
Hotel Vienna
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.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

2. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Outdoor pool
NT$8,543
NT$10,821 total
includes taxes & fees
Oct 29 - Oct 30
Wylder Hotel Windham
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 kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Pool
  • Free parking
  • Free WiFi
  • Gym
  • Laundry facilities
  • Child-friendly activities
NT$4,038
NT$4,361 total
includes taxes & fees
Nov 1 - Nov 2
The Winwood Condominiums
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 multi-story building with outdoor seating and a stone-paved patio.
A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

4. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
  • Outdoor pool
  • 2 hot tubs
NT$5,680
NT$6,764 total
includes taxes & fees
Nov 1 - Nov 2
Kaatskill Mountain Club & Condos by Vail Resorts
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 sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
A covered porch with outdoor seating, a staircase, and potted plants.

5. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Pool loungers
NT$2,413
NT$2,654 total
includes taxes & fees
Oct 18 - Oct 19
The Colonial Motel
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 building with a large front porch, a chimney, and a balcony.
A wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.

6. Moore's Motel

Moore's Motel
Prattsville
  • Outdoor pool
NT$3,823
NT$4,129 total
includes taxes & fees
Oct 6 - Oct 7
Moore's Motel
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 two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.
A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.

7. Shandaken Inn

Shandaken Inn
Shandaken
  • Pool
  • Free breakfast
  • Pet friendly
  • Free parking
  • Free WiFi
  • Gym
NT$4,530
NT$5,074 total
includes taxes & fees
Oct 29 - Oct 30
Shandaken Inn
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 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.

8. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
Saugerties
  • Indoor pool
NT$3,985
NT$4,463 total
includes taxes & fees
Oct 15 - Oct 16
Howard Johnson by Wyndham Saugerties
An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.
A buffet area with various food items, a coffee machine, and a refrigerator.
A hotel room with a bed, desk, chair, TV, and kitchenette.
A hotel room with a bed, a desk, a sofa, and two lamps.

9. Comfort Inn Saugerties

Comfort Inn Saugerties
Saugerties
  • Indoor pool
NT$4,305
NT$4,822 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn Saugerties
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.

10. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Pool umbrellas
  • Hot tub
NT$5,963
NT$6,679 total
includes taxes & fees
Nov 1 - Nov 2
Emerson Resort & Spa
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.

The Graham & Co.
Phoenicia
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
NT$5,466
NT$6,122 total
includes taxes & fees
Nov 1 - Nov 2
The Graham & Co.
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 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

Four Seasons Motel
Catskill
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
NT$3,186
NT$3,440 total
includes taxes & fees
Oct 4 - Oct 5
Four Seasons Motel
A swimming pool with lounge chairs and a red building in the background.
A compact kitchen with wooden cabinets, a refrigerator, a sink, and a dining area with a table and chairs.
A hotel room with two beds, a wooden dresser, a television, and a stone wall.
A cozy lobby with patterned sofas, a wooden reception desk, and a mirror reflecting the interior.

13. Red Ranch Motel

Red Ranch Motel
Catskill
  • Pool loungers
NT$3,402
NT$3,674 total
includes taxes & fees
Nov 1 - Nov 2
Red Ranch Motel
A swimming pool with lounge chairs, a large building, and a forested hill in the background.
A kitchen with a stove, kettle, toaster, and utensils on the counter.
A bedroom with a bed, two bedside tables, a chair, a small table, and a window.
A kitchen with a wooden shelf holding mugs and a toaster oven.

14. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
NT$5,893
NT$6,601 total
includes taxes & fees
Oct 27 - Oct 28
Catskill Seasons Inn
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 modern building with a gravel driveway and a stack of firewood in the foreground.
A triangular wooden tent with a bed inside, featuring a view of a forest with yellow foliage.

15. Eastwind Oliverea Valley

Eastwind Oliverea Valley
Big Indian
  • Outdoor pool
  • Pool loungers
NT$7,946
NT$10,426 total
includes taxes & fees
Nov 1 - Nov 2
Eastwind Oliverea Valley
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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 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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About the destination

Windham is a relaxing city where you can spend time checking out 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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