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

Windham Hotels with Swimming Pool

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Check availability on Windham Hotels with Swimming Pools

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
2 Oct - 4 Oct
Next weekend
9 Oct - 11 Oct

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 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.
A modern building with large glass doors, a staircase leading up to the entrance, and a potted plant beside the door.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
RM429
RM534 total
includes taxes & fees
6 Oct - 7 Oct
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 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.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
RM518
RM559 total
includes taxes & fees
1 Nov - 2 Nov
The Winwood Condominiums
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.
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.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
RM1,092
RM1,384 total
includes taxes & fees
29 Oct - 30 Oct
Wylder Hotel Windham
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 cozy cabin interior with a wooden ceiling, two sofas, a coffee table, a fireplace, and a television.
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
  • Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
RM728
RM867 total
includes taxes & fees
1 Nov - 2 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with lounge chairs and umbrellas.
A buffet table with various food items and a painting on the wall.
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.

5. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
RM889
RM961 total
includes taxes & fees
30 Oct - 31 Oct
Crystal Brook Resort & Mountain Brauhaus
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.

6. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
Saugerties
  • Swim in style at this Saugerties retreat with a year-round indoor pool and relaxing sauna for post-adventure recovery.
RM452
RM506 total
includes taxes & fees
2 Nov - 3 Nov
Howard Johnson by Wyndham Saugerties
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 two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.

7. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
RM580
RM650 total
includes taxes & fees
29 Oct - 30 Oct
Shandaken Inn
A swimming pool with lounge chairs and potted plants.
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.
A hotel room with two beds, a desk, a chair, and a TV on a stand.

8. 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.
RM490
RM529 total
includes taxes & fees
6 Oct - 7 Oct
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 covered porch with outdoor seating, a staircase, and potted plants.
A sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

9. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
RM364
RM400 total
includes taxes & fees
5 Oct - 6 Oct
The Colonial Motel
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Choose what matters most at hotels with a pool in Windham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Windham Hotel Reviews

Frequently asked questions

What are some accommodation options with pools in Windham?
Hotel Vienna: Hotel located near Windham Mountain Resort. Features daily, an indoor pool and free self parking. Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool and complimentary bicycles. Eastwind Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Jimmy OConnors Windham Mountain Inn: Offers a full-service spa, a seasonal outdoor pool and a snack bar/deli. The Haüs Windham: Hotel, 1-minute walk from Hunter Mountain. Provides 2 hot tubs, an outdoor pool and a sauna.
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 Windham Vineyards and Winery. 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.

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