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

Windham Hotel Guide - Hotels with Pool in Windham, New York

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Check availability on Windham Hotels with Pool

Tonight
27 Aug - 28 Aug
Tomorrow
28 Aug - 29 Aug
This weekend
28 Aug - 30 Aug
Next weekend
4 Sept - 6 Sept

Our top choices for Windham hotels with a pool

Indoor pool
Exterior
Exterior
View from room

1. Hotel Vienna

Hotel Vienna
Windham
  • Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
€122
includes taxes & fees
16 Sept - 17 Sept
Hotel Vienna
Pool
Living area
Living area
Room

2. The Winwood Condominiums

The Winwood Condominiums
Windham
  • Alpine splendour meets poolside relaxation at this mountain retreat with seasonal swim options.
€166
includes taxes & fees
30 Aug - 31 Aug
The Winwood Condominiums
Pool
Bathroom
Exterior
Restaurant

3. Wylder Hotel Windham

Wylder Hotel Windham
Windham
  • Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
€247
includes taxes & fees
30 Aug - 31 Aug
Wylder Hotel Windham
Pool
Interior
Living area
Living area

4. Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
€479
includes taxes & fees
14 Sept - 15 Sept
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Pool
Property grounds
Property grounds
Exterior

5. Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.

Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Windham
€566
includes taxes & fees
10 Sept - 11 Sept
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
Living area
Dining
Exterior
Interior

6. Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
  • Mountain village condo offers ski-in/ski-out access, heated pool, and hot tub for year-round adventures.
€786
includes taxes & fees
4 Sept - 5 Sept
Condo in Windham Mountain Village
Pool
Living area
Dining
Living area

7. Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit

Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Windham
  • Luxury mountain chalet offers year-round aquatic adventure with outdoor pool, hot tub, and water park.
€1,537
includes taxes & fees
10 Sept - 11 Sept
Ski Chalet with Pool, Hot tub, Sauna, Pizza Oven, 2 Fireplaces & Outdoor Firepit
Pool
Living area
Lobby
Exterior

8. Kaatskill Mountain Club & Condos by Vail Resorts

Kaatskill Mountain Club & Condos by Vail Resorts
Hunter
  • Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
€175
includes taxes & fees
3 Sept - 4 Sept
Kaatskill Mountain Club & Condos by Vail Resorts
Outdoor pool
Room, 2 Double Beds
Porch
Meeting facility

9. Moore's Motel

Moore's Motel
Prattsville
  • Relax in the sunshine at this quiet motel's inviting outdoor pool, surrounded by a peaceful garden setting.
€111
includes taxes & fees
1 Sept - 2 Sept
Moore's Motel
Outdoor pool
Exterior
Property entrance
Lobby sitting area

10. The Colonial Motel

The Colonial Motel
Grand Gorge
  • Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
€84
includes taxes & fees
30 Aug - 31 Aug
The Colonial Motel
View all properties

Choose what matters most at hotels with a pool in Windham

Breakfast included
Hot tub
4 stars
5 stars
Spa

Top Windham Hotel Reviews

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"good facility"
Andrea 1-night trip
Posted 1 day ago
Howard Johnson by Wyndham Saugerties

Frequently asked questions

What are some accommodation options 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. Provides free self parking, a seasonal outdoor pool and complimentary wireless Internet access. Jimmy OConnors Windham Mountain Inn: Hotel, 1-minute walk from Hunter Mountain. Features 2 hot tubs, an outdoor pool and a sauna. The Haüs Windham: Offers 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, visit sights such as Windham Country Club, Windham Mountain Resort and Catskill State Park. The mountain views, skiing and coffee shops 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 the local weather in Windham into account is an important factor for planning your visit, especially if you plan to spend your trip by the pool. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -3°C. The snowiest months in Windham are January, March, December and November, with each month seeing an average of 18 cm of snowfall.