Hotels with a Pool in Windham

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Sep 30 - Oct 1
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Oct 2 - Oct 4
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Oct 9 - Oct 11

Top 5 Hotels with a Pool in Windham at a glance

Hotels with a Pool in Windham

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 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

Hotel Vienna
Windham
  • Indoor pool
$145 nightly
$157 total
Oct 1 - Oct 2
Total with taxes and fees
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 kitchen with a central island, a black refrigerator, pendant lights, and a view through large windows.

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Pool
  • Free parking
  • Free WiFi
  • Gym
  • Laundry facilities
  • Child-friendly activities
$167 nightly
$180 total
Oct 1 - Oct 2
Total with taxes and fees
The Winwood Condominiums
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.
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.

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Outdoor pool
$361 nightly
$390 total
Oct 29 - Oct 30
Total with taxes and fees
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
  • Outdoor pool
  • 2 hot tubs
$221 nightly
$239 total
Oct 28 - Oct 29
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
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 sign for The Colonial Motel with a green and white color scheme, surrounded by lush greenery and flowering trees.

5. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Pool loungers
$81 nightly
$89 total
Oct 8 - Oct 9
Total with taxes and fees
The Colonial Motel
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 hotel room with two beds, a desk, a chair, and a TV on a stand.

6. Moore's Motel

Moore's Motel
Prattsville
  • Outdoor pool
$120 nightly
$130 total
Oct 1 - Oct 2
Total with taxes and fees
Moore's Motel
A pool area with a wooden deck, benches, and umbrellas.
A rustic room with exposed brick walls, a wooden ceiling, a sofa set, a dining table, and a chair.
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.

7. The Graham & Co.

The Graham & Co.
Phoenicia
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
$182 nightly
$203 total
Oct 5 - Oct 6
Total with taxes and fees
The Graham & Co.
A swimming pool with lounge chairs, a large building, and a forested hill in the background.
A bedroom with a bed, two bedside tables, a chair, a small table, and a window.
A kitchen with a wooden shelf holding mugs and a toaster oven.
A kitchen with a stove, kettle, toaster, and utensils on the counter.

8. Catskill Seasons Inn

Catskill Seasons Inn
Shandaken
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
$185 nightly
$207 total
Oct 27 - Oct 28
Total with taxes and fees
Catskill Seasons Inn
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 two-story house with a stone fireplace, two Adirondack chairs, and a snow-covered lawn.
A stone fireplace with a fire, two patterned armchairs, a shelf with books and a decorative owl.

9. Shandaken Inn

Shandaken Inn
Shandaken
  • Pool
  • Free breakfast
  • Pet friendly
  • Free parking
  • Free WiFi
  • Gym
$158 nightly
$177 total
Oct 29 - Oct 30
Total with taxes and fees
Shandaken Inn
A motel with a swimming pool, picnic tables, and a playground.
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.
A picnic table, playground equipment, and a swimming pool within a fenced area.

10. Four Seasons Motel

Four Seasons Motel
Catskill
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
$100 nightly
$108 total
Oct 1 - Oct 2
Total with taxes and fees
Four Seasons Motel
A log cabin with a tower, a swimming pool, and lounge chairs.
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.
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

11. Emerson Resort & Spa

Emerson Resort & Spa
Mount Tremper
  • Pool umbrellas
  • Hot tub
$207 nightly
$232 total
Oct 1 - Oct 2
Total with taxes and fees
Emerson Resort & Spa
An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.
A hotel hallway with a patterned carpet, doors on both sides, and wall-mounted lights.
A hotel room with two beds, a TV, a dresser, and a door leading to another room.
A bathroom with a granite countertop sink, a large mirror, and a shower with a glass door.

12. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
Saugerties
  • Indoor pool
$125 nightly
$140 total
Oct 4 - Oct 5
Total with taxes and fees
Howard Johnson by Wyndham Saugerties
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.

13. Red Ranch Motel

Red Ranch Motel
Catskill
  • Pool loungers
$129 nightly
$139 total
Oct 1 - Oct 2
Total with taxes and fees
Red Ranch 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.

14. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
Round Top
  • Pool
  • Free breakfast
  • Free parking
  • Free WiFi
  • Restaurant
  • Air conditioning
$218 nightly
$235 total
Oct 30 - Oct 31
Total with taxes and fees
Crystal Brook Resort & Mountain Brauhaus
A pool area with a wooden deck, benches, and a lifebuoy.
A triangular wooden tent with a bed inside, featuring a view of a forest with yellow foliage.
A wooden deck with two lounge chairs and a small table, overlooking a forested area.
A modern building with a gravel driveway and a stack of firewood in the foreground.

15. Eastwind Oliverea Valley

Eastwind Oliverea Valley
Big Indian
  • Outdoor pool
  • Pool loungers
$289 nightly
$322 total
Oct 4 - Oct 5
Total with taxes and fees
Eastwind Oliverea Valley
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.

16. Comfort Inn Saugerties

Comfort Inn Saugerties
Saugerties
  • Indoor pool
$170 nightly
$190 total
Oct 26 - Oct 27
Total with taxes and fees
Comfort Inn Saugerties
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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 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?
Book a cheap hotel in Windham with a pool from $108 and enjoy poolside fun without the premium price tag. Hotel Vienna is a top pick that includes a garden and mountain views.
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 57ºF (14ºC) to 79ºF (26ºC). It's coolest in January, which has averages of between 16ºF (-9ºC) and 27ºF (-3ºC).
Are there any hotels with a pool in Windham with parking?
You'll find 2,173 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.
Are all taxes and fees included in the Windham hotel prices shown on Hotels.com?
Hotels.com provide upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.

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