Hotels with a Pool in Windham

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Hotels with a Pool in Windham

Properties are selected based on real traveler 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 traveler experience. Last updated on .

A woman in a black swimsuit stepping out of a pool into a room with wooden ceiling beams, large windows, and wooden lounge chairs.

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
  • Indoor pool
9.4 out of 10, Exceptional, (906 reviews)
Refreshing water beckons in the pristine indoor pool, perfect for relaxation after exploring nearby hiking trails. Guests appreciate the spotless facilities, pet-friendly atmosphere, and breathtaking mountain views from private balconies.
The price is CA $157
CA $194 total
includes taxes & fees
Nov 17 - Nov 18
Hotel Vienna
A poolside area with blue chairs and umbrellas, a pool, and a building in the background.

2. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
  • Pool
  • Free parking
  • Free WiFi
  • Gym
  • Laundry facilities
  • Child-friendly activities
8.8 out of 10, Excellent, (373 reviews)
Mountain adventures await poolside at this ski-friendly hotel. Summer brings refreshing dips in the seasonal outdoor pool, while winter offers complimentary ski shuttles to nearby slopes. Spacious rooms feature incredibly comfortable beds for post-adventure relaxation.
The price is CA $236
CA $255 total
includes taxes & fees
Nov 10 - Nov 11
The Winwood Condominiums
A swimming pool with lounge chairs and umbrellas, a wooden fence, and a backdrop of a hill with trees.

3. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
  • Outdoor pool
9.0 out of 10, Wonderful, (135 reviews)
Mountain-backed swimming awaits at the seasonal outdoor pool, perfect for cooling off after complimentary bicycle rides. Guests savour craft drinks at Babblers Restaurant's happy hour before retreating to robed comfort in their well-appointed rooms.
The price is CA $304
CA $398 total
includes taxes & fees
Nov 29 - Nov 30
Wylder Hotel Windham
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

4. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
  • Outdoor pool
  • 2 hot tubs
9.2 out of 10, Wonderful, (449 reviews)
Mountain vistas frame the refreshing outdoor pool experience at this ski-in/ski-out retreat. Guests savour exceptional dining at Van Winkle's restaurant before unwinding in the sauna, steam room, and inviting hot tubs.
The price is CA $238
CA $283 total
includes taxes & fees
Nov 29 - Nov 30
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with lounge chairs and potted plants.

5. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
  • Outdoor pool
8.6 out of 10, Excellent, (183 reviews)
Poolside paradise awaits at this tranquil motel's immaculate outdoor swimming area, surrounded by garden views and picnic spots. Guests rave about the peaceful atmosphere, clean facilities, and friendly staff who make every splash more enjoyable.
The price is CA $168
CA $181 total
includes taxes & fees
Nov 6 - Nov 7
Moore's Motel
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.

6. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
  • Pool
  • Free breakfast
  • Pet friendly
  • Free parking
  • Free WiFi
  • Gym
10.0 out of 10, Exceptional, (334 reviews)
Crystalline waters of the seasonal summer pool create a refreshing mountain retreat after exploring the Catskills. Tennis courts, fire pits, and manicured grounds complete this upscale inn where delicious local breakfast awaits each morning.
The price is CA $199
CA $223 total
includes taxes & fees
Nov 8 - Nov 9
Shandaken Inn
A swimming pool with a fenced deck, lounge chairs, and umbrellas.

7. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
  • Pool loungers
9.6 out of 10, Exceptional, (504 reviews)
Swimming adventures await at the seasonal outdoor pool, where clean waters and perfectly maintained loungers create summer bliss. After poolside relaxation, this charming motel offers individually decorated rooms and access to nearby skiing, hiking, and cave exploring.
The price is CA $111
CA $122 total
includes taxes & fees
Nov 10 - Nov 11
The Colonial Motel
A swimming pool with lounge chairs and umbrellas.

8. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
2.5 star property
Round Top
  • Pool
  • Free breakfast
  • Free parking
  • Free WiFi
  • Restaurant
  • Air conditioning
9.0 out of 10, Wonderful, (102 reviews)
The price is CA $305
CA $329 total
includes taxes & fees
Nov 28 - Nov 29
Crystal Brook Resort & Mountain Brauhaus
A swimming pool with clear water, surrounded by walls with emergency contact information and pool rules.

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

Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
2.5 star property
Saugerties
  • Indoor pool
8.8 out of 10, Excellent, (825 reviews)
Immerse in the year-round indoor pool after exploring nearby hiking trails and zipline adventures. Beyond the refreshing waters, this hotel delights with spotless rooms, a hearty free breakfast, and stunning landscape views.
The price is CA $177
CA $199 total
includes taxes & fees
Nov 9 - Nov 10
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A log cabin with a tower, a swimming pool, and lounge chairs.

10. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
  • Pool umbrellas
  • Hot tub
9.0 out of 10, Wonderful, (116 reviews)
Sparkling waters await at the seasonal summer pool, perfect for refreshment after exploring hiking trails or enjoying complimentary bicycle rentals. Pamper yourself with hot stone massages at the onsite Emerson Spa before dining at The Catamount restaurant.
The price is CA $245
CA $275 total
includes taxes & fees
Nov 22 - Nov 23
Emerson Resort & Spa
A pool area with a wooden deck, benches, and umbrellas.

11. The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
9.4 out of 10, Exceptional, (68 reviews)
Seasonal outdoor pool beckons after hiking local trails or exploring on free bicycle rentals. Beyond refreshing dips, this motel offers a firepit gathering spot, playground fun, and an arcade room for entertainment throughout mountain getaways.
The price is CA $218
CA $244 total
includes taxes & fees
Nov 10 - Nov 11
The Graham & Co.
A pool area with a wooden deck, benches, and a lifebuoy.

12. Eastwind Oliverea Valley

Eastwind Oliverea Valley
3.5 star property
Big Indian
  • Outdoor pool
  • Pool loungers
9.4 out of 10, Exceptional, (61 reviews)
The price is CA $315
CA $419 total
includes taxes & fees
Dec 6 - Dec 7
Eastwind Oliverea Valley
A swimming pool with lounge chairs and a building in the background.

13. Catskill Seasons Inn

Catskill Seasons Inn
2.5 star property
Shandaken
  • Pool
  • Pet friendly
  • Free parking
  • Free WiFi
  • Air conditioning
  • Non-smoking
8.0 out of 10, Very good, (276 reviews)
Sparkling water beckons at the seasonal outdoor pool, open June through August, creating the perfect summer retreat spot. Beyond swimming, guests appreciate the tennis court, billiards table, and peaceful grounds surrounding this mountain getaway.
The price is CA $217
CA $243 total
includes taxes & fees
Nov 6 - Nov 7
Catskill Seasons Inn
A motel with a swimming pool, picnic tables, and a playground.

14. Four Seasons Motel

Four Seasons Motel
2.0 star property
Catskill
  • Pool
  • Free parking
  • Free WiFi
  • Air conditioning
8.4 out of 10, Very good, (226 reviews)
Swimming sessions await at the seasonal mountain-view pool, open May through September daily. Beyond refreshing dips, guests rave about spotless accommodations, helpful staff, and outdoor amenities including barbecue grills and a playground.
The price is CA $140
CA $151 total
includes taxes & fees
Nov 10 - Nov 11
Four Seasons Motel
An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

15. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
  • Indoor pool
7.4 out of 10, Good, (1,002 reviews)
Dive into the tranquil indoor pool after exploring nearby skiing and snowmobiling adventures. This Saugerties hotel balances aquatic relaxation with a rejuvenating sauna, garden views, and an on-site restaurant serving generous portions.
The price is CA $162
CA $182 total
includes taxes & fees
Dec 1 - Dec 2
Howard Johnson by Wyndham Saugerties
A swimming pool with lounge chairs and a red building in the background.

16. Red Ranch Motel

Red Ranch Motel
2.5 star property
Catskill
  • Pool loungers
7.4 out of 10, Good, (552 reviews)
Colourful loungers dot the seasonal outdoor pool area, where families cool off beneath shady umbrellas. Beyond refreshing swims, this spotless motel delights with an arcade room, playground, and billiards table for endless entertainment options.
The price is CA $164
CA $178 total
includes taxes & fees
Nov 9 - Nov 10
Red Ranch Motel
An indoor swimming pool with clear lane markings, a lifeguard chair, and a poolside area with a chair and table.

17. Comfort Inn Saugerties

Comfort Inn Saugerties
2.5 star property
Saugerties
  • Indoor pool
7.2 out of 10, Good, (748 reviews)
Refreshing laps await in the serene indoor pool, available from 7 AM to 10 PM for all-season swimming pleasure. After exploring nearby skiing and snowboarding options, guests appreciate returning to clean, comfortable accommodations with friendly staff.
The price is CA $203
CA $227 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn Saugerties
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Discover your perfect hotel with a pool in Windham

Breakfast included
Hot tub

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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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 CA $151 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 2,152 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.