Find Hotels with Bar in Windham, NY from CA $162

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
Nov 4 - Nov 5
Tomorrow
Nov 5 - Nov 6
This weekend
Nov 6 - Nov 8
Next weekend
Nov 13 - Nov 15

Our top choices for Windham hotels with a bar

A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

1. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (135 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is CA $304
CA $398 total
includes taxes & fees
Nov 29 - Nov 30
Wylder Hotel Windham
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

2. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (122 reviews)
"Loved the stay here as well as the friendly staff. Jamie who had helped us check in was very friendly, helpful and made us feel welcome. Location was very dog friendly. Our room was very clean, quiet and had a beautiful scene of nature. Nice place to choose for a quiet get away stay."
United States
Danica
The price is CA $316
CA $382 total
includes taxes & fees
Nov 29 - Nov 30
Eastwind Windham
A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.

3. Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
3.0 star property
Hunter
9.2 out of 10, Wonderful, (1,007 reviews)
"Always a nice stay."
United States
Marina
The price is CA $165
CA $209 total
includes taxes & fees
Nov 22 - Nov 23
Hunter Lodge, a Bluebird by Lark
A multi-story building with outdoor seating and a stone-paved patio.

4. 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, (449 reviews)
"Good overall stay, convenient location and would stay again if we visit the area."
United States
Nabeel
The price is CA $238
CA $283 total
includes taxes & fees
Nov 22 - Nov 23
Kaatskill Mountain Club & Condos by Vail Resorts
A large, two-story house with a prominent chimney, surrounded by lush greenery and a well-maintained lawn.

5. Hotel Mountain Brook

Hotel Mountain Brook
4.0 star property
Tannersville
9.8 out of 10, Exceptional, (613 reviews)
"Overall amazing stay! Location, staff, food, aesthetic and coziness all 10/10!"
United States
Kim
The price is CA $313
CA $338 total
includes taxes & fees
Nov 17 - Nov 18
Hotel Mountain Brook
A snow-covered lodge with a stone chimney, lit windows, and snow-laden trees in front.

6. Deer Mountain Inn

Deer Mountain Inn
2.0 star property
Haines Falls
9.8 out of 10, Exceptional, (14 reviews)
"Best hotel I’ve ever stayed at! Staff is so friendly and there are so many thoughtful touches, like the beautiful delicious breakfast each morning and the guest attic to hang out in upstairs. Cannot wait to come back!!"
United States
Julia
The price is CA $548
CA $629 total
includes taxes & fees
Dec 2 - Dec 3
Deer Mountain Inn
A spacious living area with a high ceiling, wooden beams, and large windows. There are multiple seating arrangements including a sofa, chairs, and a dining table.

7. AutoCamp Catskills

AutoCamp Catskills
5.0 star property
Saugerties
9.0 out of 10, Wonderful, (593 reviews)
"Very nice área to camp, everything was super clean. Would go back anytime of the year"
United States
Natalia Pérez
The price is CA $201
CA $280 total
includes taxes & fees
Dec 3 - Dec 4
AutoCamp Catskills
A snow-covered landscape with a building featuring a pond, bridge, and snow-covered trees.

8. Emerson Resort & Spa

Emerson Resort & Spa
3.5 star property
Mount Tremper
9.0 out of 10, Wonderful, (116 reviews)
"The Emmerson Resort & Spa is great! The room was super clean and the bed was very comfortable. The resort is great and has everything you need. We loved staying here!"
United States
Jeremy
The price is CA $235
CA $264 total
includes taxes & fees
Nov 22 - Nov 23
Emerson Resort & Spa
An indoor swimming pool with a brick border, surrounded by lounge chairs and tables.

9. Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.4 out of 10, Good, (1,000 reviews)
"Only stayed 1 night, but room was clean & comfortable. Would stay again in the future."
United States
Frank
The price is CA $162
CA $182 total
includes taxes & fees
Dec 1 - Dec 2
Howard Johnson by Wyndham Saugerties
A sign for Crystal Brook Resort surrounded by red tulips.

10. Crystal Brook Resort & Mountain Brauhaus

Crystal Brook Resort & Mountain Brauhaus
2.5 star property
Round Top
9.0 out of 10, Wonderful, (102 reviews)
"The property was a very classic Bavarian style resort, small and quaint, and the German food was absolutely authentic my German wife, whose mother and father come from Germany years ago I take her around the northeast looking for authentic German food that she can relate to in her childhood and this was right on spot. The breakfast cooked to order absolutely was one of the best breakfast I’ve ever had at a resort that include breakfast."
United States
Carmine
The price is CA $305
CA $329 total
includes taxes & fees
Dec 5 - Dec 6
Crystal Brook Resort & Mountain Brauhaus
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.
View all properties

Top Windham Hotel Reviews

A bar area with wooden stools, a stone wall, and a view of the outdoor seating area.
Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark
Hunter

10/10 Excellent

Great, good value place to stay, breakfast included was nice too.
Canada
David
Reviewed August 6, 2026
Hunter Lodge, a Bluebird by Lark

Frequently Asked Questions

Searching for hotels with bars in Windham?

Windham offers 268 hotels and other lodging options to choose from, and likely many will have a bar where you can unwind with a late-night cocktail. While you’re here, you can check out Windham Country Club and Windham Mountain Resort.

What are the best hotels with bars in Windham?

Here's a few of the top Windham properties with bars: Eastwind Windham: Hotel with restaurant. Enjoy the 2 bars, free WiFi, and free parking. Wylder Hotel Windham: Hotel with restaurant. Enjoy the bar, free WiFi, and free parking. Mountainside by Windham Mountain Club: Hotel with 2 restaurants. Enjoy the 2 bars, free WiFi, and free parking.

What is there to do in Windham?

To experience the area's highlights, consider visiting Windham Country Club, Windham Mountain Resort, and Windham Vineyards and Winery, and then find a cozy spot for a nightcap. Other places to see include Catskill State Park and Huntersfield State Forest. Windham is known for its ski slopes and coffeehouses.

When is the best time to visit Windham?

Visiting local bars in Windham is better in good weather. These temperatures and rainfall averages can help you decide the best time for bar hopping. 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.

How can I get to Windham and around the area?

You might want to make the most of these transportation options in and around Windham: Fly into Hudson, NY (HCC-Columbia County), which is located 27.6 mi (44.4 km) away from the heart of the city. If you'd like to explore around the area, consider renting a car to take in more sights.

Explore a world of travel with Expedia