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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 September 22, 2026.
P6,234
P7,817 total
includes taxes & fees
Oct 1 - Oct 2
2. The Winwood Condominiums
The Winwood CondominiumsWindham
- Pool
- Free parking
- Free WiFi
- Gym
- Laundry facilities
- Child-friendly activities
P9,368
P10,118 total
includes taxes & fees
Oct 1 - Oct 2
P16,023
P20,443 total
includes taxes & fees
Sep 24 - Sep 25
P7,532
P8,135 total
includes taxes & fees
Sep 23 - Sep 24
P5,593
P6,151 total
includes taxes & fees
Sep 23 - Sep 24
6. Kaatskill Mountain Club & Condos by Vail Resorts
Kaatskill Mountain Club & Condos by Vail ResortsHunter
- Outdoor pool
- 2 hot tubs
P12,405
P14,773 total
includes taxes & fees
Sep 24 - Sep 25
P8,067
P8,712 total
includes taxes & fees
Sep 23 - Sep 24
P6,277
P6,779 total
includes taxes & fees
Sep 24 - Sep 25
P8,722
P9,769 total
includes taxes & fees
Oct 5 - Oct 6
10. Crystal Brook Resort & Mountain Brauhaus
Crystal Brook Resort & Mountain BrauhausRound Top
- Pool
- Free breakfast
- Free parking
- Free WiFi
- Restaurant
- Air conditioning
P13,684
P14,779 total
includes taxes & fees
Sep 27 - Sep 28
11. The Graham & Co.
The Graham & Co.Phoenicia
- Pool
- Pet friendly
- Free parking
- Free WiFi
- Air conditioning
- Non-smoking
P10,702
P11,987 total
includes taxes & fees
Sep 28 - Sep 29
12. Catskill Seasons Inn
Catskill Seasons InnShandaken
- Pool
- Pet friendly
- Free parking
- Free WiFi
- Air conditioning
- Non-smoking
P10,043
P11,248 total
includes taxes & fees
Sep 23 - Sep 24
P10,078
P11,287 total
includes taxes & fees
Sep 27 - Sep 28
P13,817
P15,475 total
includes taxes & fees
Sep 23 - Sep 24
P12,711
P14,236 total
includes taxes & fees
Oct 1 - Oct 2
P16,141
P21,103 total
includes taxes & fees
Oct 4 - Oct 5
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.
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.
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.
Huntersfield State Forest
Huntersfield State Forest is 6.2 mi (9.9 km) from central Windham, why not stop by during your stay.
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.
Ashland Park
Ashland Park is 4.4 mi (7 km) from central Windham, why not stop by during your stay.
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 P 5,592 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 17 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 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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