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Windham Hotels with a Pool

October 2026
1
November 2026

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This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

Windham Hotels with a Pool

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 1 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 cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.
A cabin with a deck, large windows, and a mountain backdrop.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool
₹10,076
₹12,538 total
includes taxes & fees
6 Oct - 7 Oct
Hotel Vienna
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
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.
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
₹25,658
₹32,502 total
includes taxes & fees
29 Oct - 30 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 kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.
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
₹12,146
₹13,118 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 multi-story building with outdoor seating and a stone-paved patio.

4. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
  • Outdoor pool
  • 2 hot tubs
₹17,088
₹20,348 total
includes taxes & fees
1 Nov - 2 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
A covered porch with outdoor seating, a staircase, and potted plants.
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.

5. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Pool loungers
₹8,538
₹9,391 total
includes taxes & fees
5 Oct - 6 Oct
The Colonial Motel
A swimming pool with lounge chairs and umbrellas.
A cozy living room with a plaid sofa, a fireplace, and various decorative items on shelves above the fireplace.
A wooden lodge with a welcoming sign, a bear statue, and two flags.
A sign for Crystal Brook Resort surrounded by red tulips.

6. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
  • Pool
  • Free breakfast
  • Free parking
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
₹20,890
₹22,562 total
includes taxes & fees
30 Oct - 31 Oct
Crystal Brook Resort & Mountain Brauhaus
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.

7. Moore's Motel

Moore's Motel
Prattsville
  • Outdoor pool
₹11,499
₹12,419 total
includes taxes & fees
6 Oct - 7 Oct
Moore's Motel
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
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.
A stone building with a chimney, a pool, and a sign for Shandaken Inn.

8. Shandaken Inn

Shandaken Inn
Shandaken
  • Pool
  • Free breakfast
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Gym
₹13,627
₹15,262 total
includes taxes & fees
29 Oct - 30 Oct
Shandaken Inn
A pool area with a wooden deck, benches, and umbrellas.
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.
A campfire with logs and rocks in a grassy field, surrounded by trees and a building with lights in the background.

9. The Graham & Co.

The Graham & Co.
Phoenicia
  • Pool
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
  • Non-smoking
₹16,339
₹18,299 total
includes taxes & fees
1 Nov - 2 Nov
The Graham & Co.
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.

10. Four Seasons Motel

Four Seasons Motel
Catskill
  • Pool
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
₹9,583
₹10,349 total
includes taxes & fees
5 Oct - 6 Oct
Four Seasons Motel
A log cabin with a tower, a swimming pool, and lounge chairs.
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.
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.

11. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Pool umbrellas
  • Hot tub
₹18,686
₹20,929 total
includes taxes & fees
1 Nov - 2 Nov
Emerson Resort & Spa
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 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.

12. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
Saugerties
  • Indoor pool
₹11,988
₹13,427 total
includes taxes & fees
11 Oct - 12 Oct
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 hotel room with a bed, a desk, a sofa, and two lamps.
A buffet area with various food items, a coffee machine, and a refrigerator.
A reception area with a wooden reception desk, a television mounted on the wall, a blue sofa, and a fireplace with plants.

13. Comfort Inn Saugerties

Comfort Inn Saugerties
Saugerties
  • Indoor pool
₹12,951
₹14,505 total
includes taxes & fees
1 Nov - 2 Nov
Comfort Inn Saugerties
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 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.

14. Red Ranch Motel

Red Ranch Motel
Catskill
  • Pool loungers
₹10,234
₹11,053 total
includes taxes & fees
1 Nov - 2 Nov
Red Ranch Motel
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 wooden deck with two lounge chairs and a small table, overlooking a forested area.

15. Eastwind Oliverea Valley

Eastwind Oliverea Valley
Big Indian
  • Outdoor pool
  • Pool loungers
₹24,641
₹32,217 total
includes taxes & fees
1 Nov - 2 Nov
Eastwind Oliverea Valley
A swimming pool with lounge chairs, a large building, and a forested hill in the background.
A kitchen with a wooden shelf holding mugs and a toaster oven.
A two-story building with a dark exterior, surrounded by a grassy area with picnic tables.
A bedroom with a bed, two bedside tables, a chair, a small table, and a window.

16. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Pool
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
  • Non-smoking
₹17,728
₹19,855 total
includes taxes & fees
27 Oct - 28 Oct
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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Frequently Asked Questions

What are the best hotels with a pool in Windham?

One of the best Windham hotels with a pool based on guest reviews is Hotel Vienna. Make the most of an electric car charging station and mountain views here. Every day can also be a pool day at The Country Place Resort - Home of Zoom Flume Water Park, another traveller favourite.

What are the cheapest hotels with a pool in Windham?

Enjoy all the poolside perks without the splurge at Hotel Vienna. This property also offers a firepit and an electric car charging station. Check out the range of cheap hotels in Windham with a pool from ₹8,538 and live it up for less.

What is the best time to stay in a hotel with a pool in Windham?

If you'd like to visit when crowds are smaller, head here in April. You could snag some great deals on Windham hotels with a pool around that time. The warmest conditions are in July, with temperatures ranging from 14ºC to 26ºC. It's coolest in January, which has averages of between -9ºC and -3ºC.

Are there any hotels with a pool in Windham with parking?

You'll find 39 Windham hotels with a pool and parking. Pull up and go for a dip at Hotel Vienna. Mountain views and an electric car charging station are included in your stay too. Or, head to The Country Place Resort - Home of Zoom Flume Water Park, where you can easily access both parking and a pool.

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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