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Hotels with a Pool in Windham

November 2026
December 2026

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This weekend
23 Oct - 25 Oct
Next weekend
30 Oct - 1 Nov

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

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool
Rp2.092.354
Rp2.571.162 total
includes taxes & fees
9 Nov - 10 Nov
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 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.

2. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Outdoor pool
Rp2.739.012
Rp3.857.734 total
includes taxes & fees
30 Oct - 31 Oct
Wylder Hotel Windham
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 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.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Pool
  • Free parking
  • Free Wi-Fi
  • Gym
  • Laundry facilities
  • Child-friendly activities
Rp3.040.648
Rp3.283.900 total
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
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 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.

4. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
  • Outdoor pool
  • 2 hot tubs
Rp3.065.542
Rp3.650.501 total
includes taxes & fees
22 Nov - 23 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with clear water, surrounded by walls with emergency contact information and pool rules.
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.
A Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.

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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
Saugerties
  • Indoor pool
Rp2.216.706
Rp2.482.710 total
includes taxes & fees
22 Nov - 23 Nov
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A swimming pool with lounge chairs and potted plants.
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.
A two-story motel with a central staircase, balconies, and a grassy front yard.

6. Moore's Motel

Moore's Motel
Prattsville
  • Outdoor pool
Rp2.159.040
Rp2.331.763 total
includes taxes & fees
4 Nov - 5 Nov
Moore's Motel
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.

7. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Pool loungers
Rp1.603.087
Rp1.763.395 total
includes taxes & fees
25 Oct - 26 Oct
The Colonial Motel
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.

8. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
  • Pool
  • Free breakfast
  • Free parking
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
Rp3.928.796
Rp4.243.100 total
includes taxes & fees
30 Oct - 31 Oct
Crystal Brook Resort & Mountain Brauhaus
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 cabin with a chimney, surrounded by dense trees and a gravel driveway.

9. The Graham & Co.

The Graham & Co.
Phoenicia
  • Pool
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
  • Non-smoking
Rp2.810.350
Rp3.147.700 total
includes taxes & fees
2 Nov - 3 Nov
The Graham & Co.
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 breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

10. Shandaken Inn

Shandaken Inn
Shandaken
  • Pool
  • Free breakfast
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Gym
Rp2.558.462
Rp2.865.586 total
includes taxes & fees
8 Nov - 9 Nov
Shandaken Inn
A log cabin with a tower, a swimming pool, and lounge chairs.
A couple standing on a wooden deck overlooking a landscaped garden with a river view.
A hallway with intricate carvings on the walls and a large vase in the center.
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

11. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Pool umbrellas
  • Hot tub
Rp3.220.568
Rp3.607.036 total
includes taxes & fees
1 Nov - 2 Nov
Emerson Resort & Spa
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 single-story structure, a covered parking area, and a swing set in the yard.

12. Four Seasons Motel

Four Seasons Motel
Catskill
  • Pool
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
Rp1.799.200
Rp1.943.136 total
includes taxes & fees
28 Oct - 29 Oct
Four Seasons Motel
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 bathroom with a granite countertop sink, a large mirror, and a shower with a glass door.

13. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
Saugerties
  • Indoor pool
Rp1.946.376
Rp2.179.941 total
includes taxes & fees
15 Nov - 16 Nov
Howard Johnson by Wyndham Saugerties
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.

14. Red Ranch Motel

Red Ranch Motel
Catskill
  • Pool loungers
Rp1.921.546
Rp2.075.197 total
includes taxes & fees
4 Nov - 5 Nov
Red Ranch Motel
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 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.

15. Eastwind Oliverea Valley

Eastwind Oliverea Valley
Big Indian
  • Outdoor pool
  • Pool loungers
Rp4.688.063
Rp6.121.353 total
includes taxes & fees
22 Nov - 23 Nov
Eastwind Oliverea Valley
A swimming pool with lounge chairs, a large building, and a forested hill in the background.
A room with a bed, a wooden dining table, chairs, a chandelier, a fireplace, and a television.
A wooden bridge in a forested area.
A building with a sign reading 'Bar-Lodging' and an air conditioning unit mounted on the exterior wall.

16. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Pool
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
  • Non-smoking
Rp3.109.018
Rp3.481.992 total
includes taxes & fees
25 Oct - 26 Oct
Catskill Seasons Inn
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.

17. Comfort Inn Saugerties

Comfort Inn Saugerties
Saugerties
  • Indoor pool
Rp2.578.948
Rp2.888.422 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn Saugerties
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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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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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