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Windham Hotels with a Pool

October 2026
November 2026

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Next weekend
2 Oct - 4 Oct
In two weeks
9 Oct - 11 Oct

Windham Hotels with a Pool Facilities

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 27 September 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 cabin with a deck, large windows, and a mountain backdrop.
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.

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool
NZ$252
includes taxes & fees
1 Oct - 2 Oct
Hotel Vienna
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.
A compact living space with a kitchen, dining area, and seating.
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
  • Pool
  • Free parking
  • Free Wi-Fi
  • Gym
  • Laundry facilities
  • Child-friendly activities
NZ$285
includes taxes & fees
27 Sept - 28 Sept
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.
A restaurant setting with neatly arranged tables, each with a menu, plates, and glasses.
Outdoor seating with tables and chairs, a fire pit, and a wooden bridge in a park setting.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Outdoor pool
NZ$612
includes taxes & fees
27 Sept - 28 Sept
Wylder Hotel Windham
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.
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.
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
NZ$415
includes taxes & fees
26 Oct - 27 Oct
Kaatskill Mountain Club & Condos by Vail Resorts
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 sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.
A white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

5. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Pool loungers
NZ$144
includes taxes & fees
28 Sept - 29 Sept
The Colonial Motel
A swimming pool with lounge chairs and potted plants.
A two-story building with a large front porch, a chimney, and a balcony.
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.

6. Moore's Motel

Moore's Motel
Prattsville
  • Outdoor pool
NZ$229
includes taxes & fees
27 Sept - 28 Sept
Moore's Motel
A swimming pool with clear blue water, surrounded by trees and equipped with lounge chairs.
A kitchen with a wooden shelf holding mugs and a toaster oven.
A cozy room with a fireplace, a wooden table with books and glasses, and a blue sofa.
A building facade with a dark exterior, a window with blinds, a small porch with a railing, and flower planters on the porch.

7. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Pool
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
  • Non-smoking
NZ$316
includes taxes & fees
27 Sept - 28 Sept
Catskill Seasons Inn
A pool area with a wooden deck, benches, and umbrellas.
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.
A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.

8. The Graham & Co.

The Graham & Co.
Phoenicia
  • Pool
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
  • Non-smoking
NZ$337
includes taxes & fees
27 Sept - 28 Sept
The Graham & Co.
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 hallway with intricate carvings on the walls and a large vase in the center.
A couple standing on a wooden deck overlooking a landscaped garden with a river view.

9. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Pool umbrellas
  • Hot tub
NZ$418
includes taxes & fees
27 Sept - 28 Sept
Emerson Resort & Spa
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 stone building with a chimney, a pool, and a sign for Shandaken Inn.

10. Shandaken Inn

Shandaken Inn
Shandaken
  • Pool
  • Free breakfast
  • Pet-friendly
  • Free parking
  • Free Wi-Fi
  • Gym
NZ$408
includes taxes & fees
27 Sept - 28 Sept
Shandaken Inn
A swimming pool with lounge chairs and a red building in the background.
A storefront with a 'DEFACE' sign, a 'NO PETS' notice, and various seasonal decorations including pumpkins and flowers.
A hotel room with two beds, a wooden dresser, a television, and a stone wall.
A compact kitchen with wooden cabinets, a refrigerator, a sink, and a dining area with a table and chairs.

11. Red Ranch Motel

Red Ranch Motel
Catskill
  • Pool loungers
NZ$245
includes taxes & fees
28 Sept - 29 Sept
Red Ranch Motel
A motel with a swimming pool, picnic tables, and a playground.
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.
A motel with a porch, a small stream, and parked vehicles.

12. Four Seasons Motel

Four Seasons Motel
Catskill
  • Pool
  • Free parking
  • Free Wi-Fi
  • Air-conditioning
NZ$191
includes taxes & fees
27 Sept - 28 Sept
Four Seasons Motel
An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.
A restaurant with a bar area, wooden booths, and a coffee machine.
A bathroom with a granite countertop sink, a large mirror, and a shower with a glass door.
A hotel room with two beds, a TV, a dresser, and a door leading to another room.

13. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
Saugerties
  • Indoor pool
NZ$275
includes taxes & fees
27 Sept - 28 Sept
Howard Johnson by Wyndham Saugerties
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 sign for Crystal Brook Resort surrounded by red tulips.

14. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
  • Pool
  • Free breakfast
  • Free parking
  • Free Wi-Fi
  • Restaurant
  • Air-conditioning
NZ$416
includes taxes & fees
11 Oct - 12 Oct
Crystal Brook Resort & Mountain Brauhaus
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, desk, chair, TV, and kitchenette.
A buffet area with various food items, a coffee machine, and a refrigerator.
A hotel room with a bed, a desk, a sofa, and two lamps.

15. Comfort Inn Saugerties

Comfort Inn Saugerties
Saugerties
  • Indoor pool
NZ$334
includes taxes & fees
27 Sept - 28 Sept
Comfort Inn Saugerties
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 triangular wooden tent with a bed inside, featuring a view of a forest with yellow foliage.
A modern building with a gravel driveway and a stack of firewood in the foreground.

16. Eastwind Oliverea Valley

Eastwind Oliverea Valley
Big Indian
  • Outdoor pool
  • Pool loungers
NZ$590
includes taxes & fees
29 Sept - 30 Sept
Eastwind Oliverea Valley
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Discover your perfect hotel with a pool in Windham

Breakfast included
Spa pool
4 stars
5 stars
Spa

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 practise 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)
Travellers might want a tour of Windham Vineyards and Winery, just one of the places to visit, 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 NZ$143 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 the 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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