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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 21 September 2026.
2. The Winwood Condominiums
The Winwood CondominiumsWindham
- Pool
- Free parking
- Free Wi-Fi
- Gym
- Laundry facilities
- Child-friendly activities
AU$226
includes taxes & fees
22 Sept - 23 Sept
AU$461
includes taxes & fees
27 Sept - 28 Sept
4. Kaatskill Mountain Club & Condos by Vail Resorts
Kaatskill Mountain Club & Condos by Vail ResortsHunter
- Outdoor pool
- 2 hot tubs
AU$330
includes taxes & fees
23 Sept - 24 Sept
AU$132
includes taxes & fees
22 Oct - 23 Oct
AU$182
includes taxes & fees
22 Sept - 23 Sept
7. The Graham & Co.
The Graham & Co.Phoenicia
- Pool
- Pet-friendly
- Free parking
- Free Wi-Fi
- Air-conditioning
- Non-smoking
AU$255
includes taxes & fees
23 Sept - 24 Sept
AU$336
includes taxes & fees
29 Sept - 30 Sept
AU$318
includes taxes & fees
1 Oct - 2 Oct
AU$195
includes taxes & fees
22 Sept - 23 Sept
11. Catskill Seasons Inn
Catskill Seasons InnShandaken
- Pool
- Pet-friendly
- Free parking
- Free Wi-Fi
- Air-conditioning
- Non-smoking
AU$252
includes taxes & fees
22 Sept - 23 Sept
AU$219
includes taxes & fees
22 Sept - 23 Sept
13. Crystal Brook Resort & Mountain Brauhaus
Crystal Brook Resort & Mountain BrauhausRound Top
- Pool
- Free breakfast
- Free parking
- Free Wi-Fi
- Restaurant
- Air-conditioning
AU$331
includes taxes & fees
27 Sept - 28 Sept
AU$152
includes taxes & fees
22 Sept - 23 Sept
AU$253
includes taxes & fees
27 Sept - 28 Sept
AU$469
includes taxes & fees
24 Sept - 25 Sept
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 practise 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)
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.
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 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 AU$132 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 the 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.
Find out more about Windham
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 21 September 2026.
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