A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Search Hotels with Pool in Windham

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Windham Hotels with Pool

Tonight
26 Aug - 27 Aug
Tomorrow
27 Aug - 28 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sep - 6 Sep

Our top choices for Windham hotels with a pool

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 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.
A cozy cabin interior with a stone fireplace, a wooden ceiling, and a large window with curtains.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
฿4,175
฿5,074 total
includes taxes & fees
1 Sept - 2 Sept
Hotel Vienna
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
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.
A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
฿5,854
฿6,323 total
includes taxes & fees
27 Aug - 28 Aug
The Winwood Condominiums
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.
A modern bathroom with white subway tiles, a glass shower enclosure, a white sink, and a mirror.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
฿7,198
฿9,408 total
includes taxes & fees
27 Aug - 28 Aug
Wylder Hotel Windham
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
  • Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
฿6,460
฿7,692 total
includes taxes & fees
7 Sept - 8 Sept
Kaatskill Mountain Club & Condos by Vail Resorts
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 wooden bed with a floral bedspread, a small table with a vase, and a poster on the wall.
A two-story building with a large front porch, a chimney, and a balcony.

5. Moore's Motel

Moore's Motel
Prattsville
  • Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
฿3,923
฿4,236 total
includes taxes & fees
1 Sept - 2 Sept
Moore's Motel
A swimming pool with a fenced deck, lounge chairs, and umbrellas.
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.
A covered porch with outdoor seating, a staircase, and potted plants.

6. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
฿2,913
฿3,204 total
includes taxes & fees
30 Aug - 31 Aug
The Colonial Motel
View all properties

Choose what matters most at hotels with a pool in Windham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Windham Hotel Reviews

The Graham & Co.

The Graham & Co.

10/10 Excellent
"Wonderful Stay"
Daniel 2-night trip
Posted 1 day ago
The Graham & Co.
Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

10/10 Excellent
"Perfecto todo"
Miguel 1-night trip
Posted 8 days ago
Spark by Hilton West Coxsackie

Frequently asked questions

What are some accommodation options with pools in Windham?
Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Features free self parking, a seasonal outdoor pool and complimentary bicycles. Hotel Vienna: Hotel located near Windham Mountain Resort. Offers daily, an indoor pool and free self parking. Eastwind Windham: Hotel located near Windham Mountain Resort. Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Jimmy OConnors Windham Mountain Inn: Hotel, 1-minute walk from Hunter Mountain. Features 2 hot tubs, an outdoor pool and a sauna. The Haüs Windham: Offers a full-service spa, a seasonal outdoor pool and complimentary bicycles.
What is there to see and do in Windham?
Surround yourself with nature at Elm Ridge Wild Forest and Ashland Park. During your stay, visit sights such as Windham Country Club, Windham Mountain Resort and Catskill State Park. The mountain views, skiing and coffee shops are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Windham?
Taking the local weather in Windham into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.

Explore a world of travel with Expedia