A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.

Find Hotels with a Pool in Windham, NY

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Check availability on Windham Hotels with a Pool

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

Our top choices for Windham hotels with a pool

Indoor pool

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (835 reviews)
  • cleanliness
    Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
The price is ₩192,068
₩232,374 total
includes taxes & fees
Aug 9 - Aug 10
Hotel Vienna
Seasonal outdoor pool

2. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (358 reviews)
  • cleanliness
    Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
The price is ₩234,491
₩253,257 total
includes taxes & fees
Aug 3 - Aug 4
The Winwood Condominiums
Outdoor pool

3. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (108 reviews)
  • cleanliness
    Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
The price is ₩317,667
₩415,209 total
includes taxes & fees
Aug 20 - Aug 21
Wylder Hotel Windham
Outdoor pool

4. Moore's Motel

Moore's Motel
2.5 star property
Prattsville
8.6 out of 10, Excellent, (174 reviews)
  • cleanliness
    Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
The price is ₩173,112
₩186,961 total
includes taxes & fees
Aug 2 - Aug 3
Moore's Motel
Seasonal outdoor pool, pool umbrellas, sun loungers

5. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (465 reviews)
  • cleanliness
    Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
The price is ₩128,535
₩141,388 total
includes taxes & fees
Aug 2 - Aug 3
The Colonial Motel
Seasonal outdoor pool

6. Four Seasons Motel

Four Seasons Motel
2.0 star property
Catskill
8.4 out of 10, Very Good, (217 reviews)
  • cleanliness
    Seasonal mountain pool paradise invites guests to cool off with refreshing dips from May to September.
The price is ₩144,260
₩155,801 total
includes taxes & fees
Aug 3 - Aug 4
Four Seasons Motel
Outdoor pool

7. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
2.0 star property
Hunter
9.2 out of 10, Wonderful, (401 reviews)
  • cleanliness
    Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
The price is ₩299,423
₩356,557 total
includes taxes & fees
Aug 11 - Aug 12
Kaatskill Mountain Club & Condos by Vail Resorts
Seasonal outdoor pool, open 10 AM to 8 PM, pool umbrellas, sun loungers

8. Red Ranch Motel

Red Ranch Motel
2.5 star property
Catskill
7.2 out of 10, Good, (513 reviews)
  • cleanliness
    Dive into seasonal poolside bliss with dedicated children's swimming areas and shady loungers at this Hudson Valley retreat.
The price is ₩185,403
₩200,233 total
includes taxes & fees
Aug 5 - Aug 6
Red Ranch Motel
Indoor pool

9. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1,000 reviews)
  • cleanliness
    Swim in style at this Saugerties retreat with a year-round indoor pool and relaxing sauna for post-adventure recovery.
The price is ₩157,099
₩175,968 total
includes taxes & fees
Aug 30 - Aug 31
Howard Johnson by Wyndham 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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Choose what matters most at hotels with a pool in Windham

Breakfast included
Hot tub

Top Windham Hotel Reviews

The Graham & Co.

The Graham & Co.

10/10 Excellent
"Beautiful location with the vibe of a vintage motel, but the updates and amenities of a more pampered stay. The staff were very helpful and kind, and floating in the pool after a long-day's drive was so refreshing. We definitely be staying here on future trips to the area!"
Kathleen 1-night trip
Posted 2 days ago
The Graham & Co.

Frequently asked questions

What are some accommodations with pools in Windham?
Wylder Hotel Windham: Hotel located near Windham Mountain Resort. Features free self parking, a seasonal outdoor pool, and complimentary bicycles. Hotel Vienna: Hotel located near Windham Mountain Resort. Offers daily, an indoor pool, and free self parking. Eastwind Windham: Hotel located near Windham Mountain Resort. Offers free self parking, a seasonal outdoor pool, and complimentary wireless internet access. Jimmy OConnors Windham Mountain Inn: Provides a sauna, an indoor pool, and free self parking. The Haüs Windham: Features a full-service spa, a seasonal outdoor pool, and complimentary bicycles.
What is there to see and do in Windham?
Surround yourself with nature at Elm Ridge Wild Forest and Ashland Park. During your stay, check out sights such as Windham Country Club, Windham Mountain Resort, and Catskill State Park. The mountain views, skiing, and coffeehouses are just some of the things to enjoy while you're in the area.
When is the best time to book a hotel with a pool in Windham?
Taking into account the local weather in Windham is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 27°F. The snowiest months in Windham are January, March, December, and November, with each month seeing an average of 7 inches of snowfall.