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 October 12, 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 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.

A cabin with a deck, large windows, and a mountain backdrop.

1. Hotel Vienna

Windham

Indoor pool

P6,239

P7,823 total

includes taxes & fees

Oct 29 - Oct 30

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 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.

2. Wylder Hotel Windham

Windham

Outdoor pool

P16,820

P21,307 total

includes taxes & fees

Oct 13 - Oct 14

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.

3. The Winwood Condominiums

Windham

Pool
Free parking
Free WiFi
Gym
Laundry facilities
Child-friendly activities

P10,617

P11,466 total

includes taxes & fees

Nov 1 - Nov 2

A swimming pool with clear water, surrounded by walls with emergency contact information and pool rules.

A hotel lobby with a reception desk, seating area, and a corridor leading to other rooms.

A modern lobby with a reception desk, seating area, and a dining section.

A modern breakfast area with a coffee machine, cereal, and bakery options.

4. Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG

Saugerties

Indoor pool

P7,978

P8,936 total

includes taxes & fees

Nov 11 - Nov 12

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 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.

5. Kaatskill Mountain Club & Condos by Vail Resorts

Hunter

Outdoor pool
2 hot tubs

P11,202

P13,339 total

includes taxes & fees

Nov 10 - Nov 11

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 white colonial-style building with green shutters, a porch with a swing, and hanging flower baskets.

6. The Colonial Motel

Grand Gorge

Pool loungers

P5,597

P6,156 total

includes taxes & fees

Oct 14 - Oct 15

A swimming pool with lounge chairs and umbrellas.

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.

A sign for Crystal Brook Resort surrounded by red tulips.

7. Crystal Brook Resort & Mountain Brauhaus

Round Top

Pool
Free breakfast
Free parking
Free WiFi
Restaurant
Air conditioning

P13,695

P14,791 total

includes taxes & fees

Oct 30 - Oct 31

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 hotel room with two beds, a desk, a chair, and a TV on a stand.

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

8. Moore's Motel

Prattsville

Outdoor pool

P7,539

P8,142 total

includes taxes & fees

Oct 13 - Oct 14

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

9. Shandaken Inn

Shandaken

Pool
Free breakfast
Pet friendly
Free parking
Free WiFi
Gym

P8,933

P10,006 total

includes taxes & fees

Oct 27 - Oct 28

A modern dining area with wooden tables and benches, green chairs, and pendant lighting.

A hotel lobby with orange rocking chairs, a reception desk, and a green carpet.

A hotel room with a wooden desk, a television, a grey office chair, a sofa, and a window with curtains.

A hotel room with two beds, a desk, a chair, a TV, and a window with curtains.

10. Spark by Hilton West Coxsackie

West Coxsackie

Indoor pool

P6,888

P7,439 total

includes taxes & fees

Nov 8 - Nov 9

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, a desk, a sofa, and two lamps.

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

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

11. Comfort Inn Saugerties

Saugerties

Indoor pool

P8,990

P10,068 total

includes taxes & fees

Nov 1 - Nov 2

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 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.

12. Four Seasons Motel

Catskill

Pool
Free parking
Free WiFi
Air conditioning

P6,282

P6,785 total

includes taxes & fees

Oct 13 - Oct 14

An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

A bathroom with a granite countertop sink, a large mirror, and a shower with a glass door.

A restaurant with a bar area, wooden booths, and a coffee machine.

A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.

13. Howard Johnson by Wyndham Saugerties

Saugerties

Indoor pool

P6,898

P7,725 total

includes taxes & fees

Nov 2 - Nov 3

A pool area with a wooden deck, benches, and umbrellas.

A rustic cabin with a chimney, surrounded by dense trees and a gravel driveway.

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

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

14. The Graham & Co.

Phoenicia

Pool
Pet friendly
Free parking
Free WiFi
Air conditioning
Non-smoking

P9,813

P10,991 total

includes taxes & fees

Nov 2 - Nov 3

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

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

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.

15. Red Ranch Motel

Catskill

Pool loungers

P6,709

P7,246 total

includes taxes & fees

Nov 1 - Nov 2

A log cabin with a tower, a swimming pool, and lounge chairs.

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

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.

16. Emerson Resort & Spa

Mount Tremper

Pool umbrellas
Hot tub

P11,245

P12,594 total

includes taxes & fees

Nov 1 - Nov 2

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 wooden deck with two lounge chairs and a small table, overlooking a forested area.

A triangular wooden tent with a bed inside, featuring a view of a forest with yellow foliage.

17. Eastwind Oliverea Valley

Big Indian

Outdoor pool
Pool loungers

P16,342

P21,337 total

includes taxes & fees

Oct 20 - Oct 21

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

A building facade with a dark exterior, a window with blinds, a small porch with a railing, and flower planters on the porch.

A hotel room with two single beds, a nightstand with a lamp, and a dark blue accent wall.

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

18. Catskill Seasons Inn

Shandaken

Pool
Pet friendly
Free parking
Free WiFi
Air conditioning
Non-smoking

P10,868

P12,172 total

includes taxes & fees

Nov 3 - Nov 4

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Discover your perfect hotel with a pool in Windham

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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 practice 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)

Travelers might want a tour of Windham Vineyards and Winery, just one of the places to visit, and 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 traveler favorite.

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 P6,156 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 2,164 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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