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

Our top choices for Windham hotels with a pool

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
9.4 out of 10, Exceptional, (916 reviews)
  • cleanliness
    Indoor pool sanctuary with mountain views offers year-round swimming and complimentary bikes for adventure seekers.
$141 nightly
The price is $152
Nov 16 - Nov 17
Total with taxes and fees
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
8.8 out of 10, Excellent, (378 reviews)
  • cleanliness
    Alpine splendor meets poolside relaxation at this mountain retreat with seasonal swim options.
$169 nightly
The price is $183
Nov 16 - Nov 17
Total with taxes and fees
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
9.0 out of 10, Wonderful, (139 reviews)
  • cleanliness
    Splash into mountain adventures at this outdoor pool haven with free bikes and seasonal poolside relaxation.
$249 nightly
The price is $269
Nov 18 - Nov 19
Total with taxes and fees
Wylder Hotel Windham
An indoor swimming pool area with a hot tub, seating, and a caution sign.

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.0 out of 10, Wonderful, (9 reviews)
$478 nightly
The price is $516
Nov 16 - Nov 17
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

5. Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (16 reviews)
  • cleanliness
    Mountain village condo offers ski-in/ski-out access, heated pool, and hot tub for year-round adventures.
$679 nightly
The price is $733
Nov 21 - Nov 22
Total with taxes and fees
Condo in Windham Mountain Village
A multi-story hotel with a swimming pool, balconies, and outdoor seating areas.

6. 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, (453 reviews)
  • cleanliness
    Dive into mountain paradise at Hunter's sun-soaked pool with sauna and picturesque views.
$160 nightly
The price is $173
Nov 22 - Nov 23
Total with taxes and fees
Kaatskill Mountain Club & Condos by Vail Resorts
A swimming pool with a fenced deck, lounge chairs, and umbrellas.

7. The Colonial Motel

The Colonial Motel
2.5 star property
Grand Gorge
9.6 out of 10, Exceptional, (505 reviews)
  • cleanliness
    Sparkling outdoor pool beckons with sun loungers and umbrellas at this relaxing motel retreat.
$86 nightly
The price is $95
Nov 18 - Nov 19
Total with taxes and fees
The Colonial Motel
A large house with a swimming pool surrounded by a fence, a tennis court, and a grassy lawn.

8. Shandaken Inn

Shandaken Inn
4.0 star property
Shandaken
10.0 out of 10, Exceptional, (335 reviews)
  • cleanliness
    Seasonal pool bliss in the Catskills invites summer splashes at this charming inn.
$158 nightly
The price is $177
Nov 16 - Nov 17
Total with taxes and fees
Shandaken Inn
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
8.8 out of 10, Excellent, (832 reviews)
  • cleanliness
    Dive into refreshing escapes at this indoor pool sanctuary with post-adventure relaxation vibes.
$131 nightly
The price is $147
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Saugerties - Hudson Valley by IHG
A pool area with a wooden deck, benches, and umbrellas.

10. The Graham & Co.

The Graham & Co.
3.0 star property
Phoenicia
9.4 out of 10, Exceptional, (69 reviews)
  • cleanliness
    Splash into poolside fun at this Catskill Mountains motel, where seasonal swimming meets adventure in a charming outdoor oasis.
$109 nightly
The price is $122
Nov 16 - Nov 17
Total with taxes and fees
The Graham & Co.
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

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties

8/10 Good
"Comfortable beds"
Margaret 1-night trip
Posted 4 days ago
Howard Johnson by Wyndham Saugerties

Frequently asked questions

How much does a hotel with outdoor pool in Windham cost?
Enjoy staying in a hotel in Windham with an outdoor pool. You can find a great deal from $95 on Expedia. If you're leaning toward a little luxury, prices can rise, and may vary depending on the location, season, and hotel amenities. Be sure to book in advance to enjoy more options and potentially better rates, especially if you're planning a trip during weekends or around public holidays.
Are there hotels in Windham with outdoor pool activities or events?
Windham, New York, is a charming mountain town known for its stunning natural landscapes and outdoor activities. Travellers seeking a refreshing retreat will be pleased to discover that several hotels in the area offer outdoor pool activities. The Wylder Windham stands out as a fantastic option, featuring a heated outdoor pool complemented by wood-fired barrel saunas, superb for unwinding after a day of hiking or skiing.

For families, the Winwood Inn & Condominiums is another excellent choice, boasting an outdoor pool that is open during the summer season. This welcoming atmosphere, combined with spacious rooms, makes it an ideal spot for families looking to relax and enjoy quality time together.
Is it cheaper to book flights and a Windham hotel with a pool as a package?
Booking a hotel and flight package on Expedia can be cheaper than booking flights and hotels separately. Bundling can lead to significant savings, especially for international travel or when booking well in advance. However, savings vary depending on factors like destination, travel dates and availability, so it's wise to compare options. With access to over 300,000 hotels worldwide, Expedia makes it easy to build the perfect vacation package.
Can I cancel my hotel reservation on Expedia?
Expedia has plenty of refundable hotels. In many cases, you need to cancel your booking 24-48 hours ahead of your arrival date. Remember to check your booking confirmation for the exact cancellation policy. For maximum flexibility, use Expedia's "Fully refundable property" filter during your search to find the right hotel in Windham for you.

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