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Hotels with a Pool in Windham

October 2026
13
November 2026

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Oct 16 - Oct 18
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Oct 23 - Oct 25

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 14, 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 cabin with a deck, large windows, and a mountain backdrop.
A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool
CNY665
CNY834 total
includes taxes & fees
Oct 29 - Oct 30
Hotel Vienna
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
A modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.
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.

2. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Outdoor pool
CNY1,792
CNY2,270 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 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.

3. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Pool
  • Free parking
  • Free WiFi
  • Gym
  • Laundry facilities
  • Child-friendly activities
CNY1,131
CNY1,222 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 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.

4. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
  • Outdoor pool
  • 2 hot tubs
CNY1,194
CNY1,421 total
includes taxes & fees
Nov 11 - Nov 12
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 Holiday Inn Express hotel with a covered entrance, multiple floors, and a brick facade.
A modern lobby with a reception desk, seating area, and a dining section.

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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
Saugerties
  • Indoor pool
CNY850
CNY952 total
includes taxes & fees
Nov 11 - Nov 12
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A swimming pool with lounge chairs and umbrellas.
A buffet table with various food items and a painting on the wall.
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.

6. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
  • Pool
  • Free breakfast
  • Free parking
  • Free WiFi
  • Restaurant
  • Air conditioning
CNY1,459
CNY1,576 total
includes taxes & fees
Oct 30 - Oct 31
Crystal Brook Resort & Mountain Brauhaus
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 two-story motel with a central staircase, balconies, and a grassy front yard.

7. Moore's Motel

Moore's Motel
Prattsville
  • Outdoor pool
CNY803
CNY868 total
includes taxes & fees
Oct 14 - Oct 15
Moore's Motel
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 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.

8. Shandaken Inn

Shandaken Inn
Shandaken
  • Pool
  • Free breakfast
  • Pet friendly
  • Free parking
  • Free WiFi
  • Gym
CNY952
CNY1,066 total
includes taxes & fees
Oct 27 - Oct 28
Shandaken Inn
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
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".
A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

9. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Pool loungers
CNY596
CNY656 total
includes taxes & fees
Oct 25 - Oct 26
The Colonial Motel
A modern dining area with wooden tables and benches, green chairs, and pendant lighting.
A hotel lobby with orange rocking chairs, a reception desk, and a green carpet.
A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.
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

Spark by Hilton West Coxsackie
West Coxsackie
  • Free breakfast
  • Pet friendly
  • Free parking
  • Free WiFi
  • Connecting rooms available
  • Air conditioning
CNY791
CNY854 total
includes taxes & fees
Nov 8 - Nov 9
Spark by Hilton West Coxsackie
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, desk, chair, TV, and kitchenette.
A hotel room with a bed, a desk, a sofa, and two lamps.

11. Comfort Inn Saugerties

Comfort Inn Saugerties
Saugerties
  • Indoor pool
CNY958
CNY1,073 total
includes taxes & fees
Nov 1 - Nov 2
Comfort Inn Saugerties
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.

12. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
Saugerties
  • Indoor pool
CNY735
CNY823 total
includes taxes & fees
Nov 2 - Nov 3
Howard Johnson by Wyndham Saugerties
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 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.

13. The Graham & Co.

The Graham & Co.
Phoenicia
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
CNY1,045
CNY1,171 total
includes taxes & fees
Nov 3 - Nov 4
The Graham & Co.
A motel with a swimming pool, picnic tables, and a playground.
A picnic table, playground equipment, and a swimming pool within a fenced area.
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.

14. Four Seasons Motel

Four Seasons Motel
Catskill
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
CNY669
CNY723 total
includes taxes & fees
Oct 25 - Oct 26
Four Seasons Motel
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 spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

15. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Pool umbrellas
  • Hot tub
CNY1,198
CNY1,342 total
includes taxes & fees
Nov 3 - Nov 4
Emerson Resort & Spa
A pool area with a wooden deck, benches, and a lifebuoy.
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.
A wooden deck with two lounge chairs and a small table, overlooking a forested area.

16. Eastwind Oliverea Valley

Eastwind Oliverea Valley
Big Indian
  • Outdoor pool
  • Pool loungers
CNY1,781
CNY2,320 total
includes taxes & fees
Oct 20 - Oct 21
Eastwind Oliverea Valley
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.

17. Red Ranch Motel

Red Ranch Motel
Catskill
  • Pool loungers
CNY715
CNY772 total
includes taxes & fees
Nov 1 - Nov 2
Red Ranch Motel
A swimming pool with lounge chairs and a building in the background.
A bathroom with a toilet, a bathtub, and a shower.
A building facade with a dark exterior, a window with blinds, a small porch with a railing, and flower planters on the porch.
A hotel room with two single beds, a nightstand with a lamp, and a dark blue accent wall.

18. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
CNY1,158
CNY1,297 total
includes taxes & fees
Nov 3 - Nov 4
Catskill Seasons Inn
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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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