Windham Hotels with a Pool

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

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.

1. Hotel Vienna

Windham

Indoor pool

S$190

includes taxes & fees

5 Oct - 6 Oct

A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

A dining area with wooden chairs and a table, a kitchen with a window and a blackboard, and a staircase leading to another level.

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.

2. The Winwood Condominiums

Windham

Pool
Free parking
Free Wi-Fi
Gym
Laundry facilities
Child-friendly activities

S$175

includes taxes & fees

1 Nov - 2 Nov

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.

3. Wylder Hotel Windham

Windham

Outdoor pool

S$433

includes taxes & fees

29 Oct - 30 Oct

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 multi-story building with outdoor seating and a stone-paved patio.

A large hotel with multiple floors, a parking lot, and a mountainous backdrop.

4. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Outdoor pool
2 hot tubs

S$271

includes taxes & fees

1 Nov - 2 Nov

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

Grand Gorge

Pool loungers

S$118

includes taxes & fees

13 Oct - 14 Oct

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 breakfast table with a painting of a barn, bowls of fruit, pastries, and a toaster.

6. Shandaken Inn

Shandaken

Pool
Free breakfast
Pet-friendly
Free parking
Free Wi-Fi
Gym

S$204

includes taxes & fees

29 Oct - 30 Oct

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 building with a large front porch, a chimney, and a balcony.

A two-story motel with a central staircase, balconies, and a grassy front yard.

7. Moore's Motel

Prattsville

Outdoor pool

S$166

includes taxes & fees

1 Nov - 2 Nov

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 corridor with white walls, wooden slats, and a concrete floor.

A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.

8. The Graham & Co.

Phoenicia

Pool
Pet-friendly
Free parking
Free Wi-Fi
Air-conditioning
Non-smoking

S$244

includes taxes & fees

1 Nov - 2 Nov

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 spacious dining area with wooden beams, large windows, and a central island with tables and chairs.

9. Emerson Resort & Spa

Mount Tremper

Pool umbrellas
Hot tub

S$268

includes taxes & fees

1 Nov - 2 Nov

A motel with a swimming pool, picnic tables, and a playground.

A picnic table, playground equipment, and a swimming pool within a fenced area.

A motel with a single-story structure, a covered parking area, and a swing set in the yard.

A hotel room with two beds, a nightstand with a lamp, and a window with floral curtains.

10. Four Seasons Motel

Catskill

Pool
Free parking
Free Wi-Fi
Air-conditioning

S$138

includes taxes & fees

4 Oct - 5 Oct

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.

11. Eastwind Oliverea Valley

Big Indian

Outdoor pool
Pool loungers

S$418

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with lounge chairs and a red building in the background.

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.

A cozy lobby with patterned sofas, a wooden reception desk, and a mirror reflecting the interior.

12. Red Ranch Motel

Catskill

Pool loungers

S$147

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with lounge chairs, a large building, and a forested hill in the background.

A two-story building with a dark exterior, surrounded by a grassy area with picnic tables.

A kitchen with a stove, kettle, toaster, and utensils on the counter.

A kitchen with a wooden shelf holding mugs and a toaster oven.

13. Catskill Seasons Inn

Shandaken

Pool
Pet-friendly
Free parking
Free Wi-Fi
Air-conditioning
Non-smoking

S$259

includes taxes & fees

27 Oct - 28 Oct

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.

14. Howard Johnson by Wyndham Saugerties

Saugerties

Indoor pool

S$179

includes taxes & fees

14 Oct - 15 Oct

An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.

A reception area with a wooden reception desk, a television mounted on the wall, a blue sofa, and a fireplace with plants.

A hotel room with a bed, desk, chair, TV, and kitchenette.

A buffet area with various food items, a coffee machine, and a refrigerator.

15. Comfort Inn Saugerties

Saugerties

Indoor pool

S$193

includes taxes & fees

1 Nov - 2 Nov

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Discover your perfect hotel with a pool in Windham

Breakfast included

Hot tub

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 S$138 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 2,170 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.

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