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Hotels with Swimming Pools in Windham

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Check availability on Windham Hotels with Swimming Pools

Tonight
6 Oct - 7 Oct
Tomorrow
7 Oct - 8 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 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 log cabin with a deck, outdoor seating, and a view of a forest.
A cabin with a deck, large windows, and a mountain backdrop.
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.
S$183
includes taxes & fees
29 Oct - 30 Oct
Hotel Vienna
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 compact living space with a kitchen, dining area, and seating.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
S$175
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.
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.
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.
S$434
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 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
  • Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
S$272
includes taxes & fees
4 Nov - 5 Nov
Kaatskill Mountain Club & Condos by Vail Resorts
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.
A breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.
A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.
A two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.

5. Shandaken Inn

Shandaken Inn
Shandaken
  • Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
S$204
includes taxes & fees
27 Oct - 28 Oct
Shandaken Inn
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 covered porch with outdoor seating, a staircase, and potted plants.
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".

6. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
S$115
includes taxes & fees
8 Oct - 9 Oct
The Colonial Motel
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.

7. 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.
S$166
includes taxes & fees
7 Oct - 8 Oct
Moore's 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 buffet table with various food items and a painting on the wall.
A wooden lodge with a welcoming sign, a bear statue, and two flags.

8. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
S$301
includes taxes & fees
30 Oct - 31 Oct
Crystal Brook Resort & Mountain Brauhaus
A pool area with a wooden deck, benches, and umbrellas.
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.
A corridor with white walls, wooden slats, and a concrete floor.

9. The Graham & Co.

The Graham & Co.
Phoenicia
  • Splash into poolside fun at this Catskill Mountains motel, where seasonal swimming meets adventure in a charming outdoor oasis.
S$224
includes taxes & fees
2 Nov - 3 Nov
The Graham & Co.
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

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie

10/10 Excellent
"Clean and well maintained hotel."
Uri 1-night trip
Posted 2 days ago
Spark by Hilton West Coxsackie
Hotel Vienna

Hotel Vienna

8/10 Good
"Very clean and well kept place. The pool area is lovely as well. The breakfast was mostly sugar stuff though… with lots of pastries and sweetened yogurts, and only caffeinated coffee available. Be sure to prepare accordingly if you have dietary restrictions. We enjoyed our stay and the location."
Cindi 1-night trip
Posted 2 days ago
Hotel Vienna
Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

10/10 Excellent
"The room was clean and staff very pleasant and helpful. I would stay again."
Shirley 1-night trip
Posted 2 days ago
Howard Johnson by Wyndham Saugerties

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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