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

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Check prices for these dates

Next weekend
Oct 23 - Oct 25
In two weeks
Oct 30 - Nov 1
In one month
Nov 13 - Nov 15
In two months
Dec 11 - Dec 13
No exact matches found, but these alternatives could be just right

Recommended hotels in Windham

A log cabin with a deck, outdoor seating, and a view of a forest.

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (886 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is CA $165
CA $202 total
includes taxes & fees
Oct 29 - Oct 30
Hotel Vienna
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

2. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (368 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is CA $239
CA $258 total
includes taxes & fees
Nov 9 - Nov 10
The Winwood Condominiums
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

3. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
9.2 out of 10, Wonderful, (10 reviews)
"We had a wedding in the area and this place was perfect for our needs. There’s a bar to the front of the property, which was fun to hang out and play pool. The beds were comfortable and the rooms were clean."
United States
Robin
The price is CA $189
CA $204 total
includes taxes & fees
Oct 18 - Oct 19
Jimmy OConnors Windham Mountain Inn
A large, two-story house with multiple porches and string lights.

4. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (289 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is CA $246
CA $265 total
includes taxes & fees
Oct 18 - Oct 19
Albergo Allegria Hotel
A two-story house with a stone chimney, a porch with flower boxes, and a well-maintained lawn.

5. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (150 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is CA $197
CA $212 total
includes taxes & fees
Nov 4 - Nov 5
Cave Mountain Motel
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

6. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (138 reviews)
"A fantastic stay!"
United States
David
The price is CA $191
CA $206 total
includes taxes & fees
Oct 19 - Oct 20
Antique Rose Inn Windham
A wooden cabin with a triangular roof, a wooden door, and a bench outside.

7. Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (121 reviews)
"The cabin was adorable, everything at Dandies was delicious and Jamie was extremely helpful"
United States
Sharon
The price is CA $316
CA $383 total
includes taxes & fees
Nov 15 - Nov 16
Eastwind Windham
A large, white, multi-story building with a central courtyard, surrounded by lush greenery and a hilly landscape.

8. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (131 reviews)
"Loved our stay, will go anytime for a little weekend getaway from nyc!"
United States
Yassaman Modarres
The price is CA $215
CA $303 total
includes taxes & fees
Oct 30 - Oct 31
Wylder Hotel Windham
A two-story building with large windows and a storefront.

9. Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Windham
9.2 out of 10, Wonderful, (45 reviews)
"Perfect stay cozy and convenient "
United States
Ahmad O.
The price is CA $106
CA $191 total
includes taxes & fees
Nov 1 - Nov 2
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A bedroom with a large window, a bed, and a view of a forest.

10. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (39 reviews)
"Easy check in, nice layout of the apt, comfortable bed, nice to have a kitchen. Nearby lots of restaurants and mountain access. "
United States
Erica
The price is CA $252
CA $484 total
includes taxes & fees
Nov 17 - Nov 18
The Haüs Windham
A two-story building with large windows and a storefront.

11. TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Windham
9.0 out of 10, Wonderful, (64 reviews)
"Very nice hosts! Will come back again. Thanks very much!!"
United States
juneid a.
The price is CA $156
CA $276 total
includes taxes & fees
Nov 4 - Nov 5
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.6 out of 10, Exceptional, (8 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is CA $271
CA $743 total
includes taxes & fees
Oct 21 - Oct 22
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A kitchen with green cabinets, a stainless steel stove, and a microwave.

13. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn

1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
Windham
7.6 out of 10, Good, (5 reviews)
"Excellent accommodations, close to everything you could need. My wife and I had a perfect evening "
United States
Anthony M.
The price is CA $244
CA $314 total
includes taxes & fees
Nov 3 - Nov 4
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mtn
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

14. 2 Min Walk to Windham Town | Hot Tub | Fire Pit

2 Min Walk to Windham Town | Hot Tub | Fire Pit
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Great location, perfect layout and responsive host! Thanks for hosting - would gladly stay again. "
United States
Melissa R.
The price is CA $302
CA $794 total
includes taxes & fees
Nov 9 - Nov 10
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

15. Pines Vignette • Modern 3BR Home in Windham

Pines Vignette • Modern 3BR Home in Windham
Windham
10.0 out of 10, Exceptional, (2 reviews)
"House is cozy and has everything you need. We enjoyed our stay."
United States
William H.
The price is CA $260
CA $741 total
includes taxes & fees
Nov 1 - Nov 2
Pines Vignette • Modern 3BR Home in Windham
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

16. Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain

Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
Windham
7.6 out of 10, Good, (5 reviews)
"This was a unique and fun VRBO experience. The cabin was cozy and comfortable.So delightful to wake up to deer walking right by the window! Absolutely a gem of a property!"
United States
Erin J.
The price is CA $331
CA $431 total
includes taxes & fees
Oct 28 - Oct 29
Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
A fire pit with two chairs in a backyard.

17. Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn

Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
Windham
The price is CA $493
CA $886 total
includes taxes & fees
Nov 2 - Nov 3
Private 5BR Chalet Sleeping 12 with Fire Pit near Windham Mtn
An outdoor patio area with a pergola, seating, and a barbecue grill.

18. Tiny House on Walnut Grove

Tiny House on Walnut Grove
Ashland
4.0 out of 10, (2 reviews)
"Many problems with this listing, first the fire alarm was low on battery, I had to physically climb to reach the smoke detector to detach and remove the battery, a sharp beeping noise went off every 90 seconds and we wouldn’t have been able to sleep without stopping it. There were no spare batteries to change. There were spiders everywhere. My friend used the shower and saw 11 of them moving around the ceiling. They were in the main bed and on the counter and sink as well. The tenant was nice...
United States
Trevor C.
The price is CA $286
CA $609 total
includes taxes & fees
Oct 18 - Oct 19
Tiny House on Walnut Grove
A hot tub with a fire pit, surrounded by Adirondack chairs, and string lights.

19. Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain

Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
Windham
The price is CA $703
CA $1,504 total
includes taxes & fees
Nov 16 - Nov 17
Luxury Windham Escape w/ Hot Tub, Views & Walk to Mountain
A cozy living room with wooden walls, a stone fireplace, and a television.

20. Beautiful Windham Chalet 2 minutes to Town and the Mountain

Beautiful Windham Chalet 2 minutes to Town and the Mountain
Windham
10.0 out of 10, Exceptional, (3 reviews)
"Very easy to check in and check out. Very excellent instructions and welcoming atmosphere. "
United States
John K.
The price is CA $615
CA $1,021 total
includes taxes & fees
Oct 19 - Oct 20
Beautiful Windham Chalet 2 minutes to Town and the Mountain
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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Top Windham Hotel Reviews

Urban Cowboy Lodge

Urban Cowboy Lodge

10/10 Excellent
"Overall fantastic stay. The property itself is beautiful and you can see it being upkept constantly, it is clear that they are taking great care of it while still maintaining the charm. The rooms were spotless both where we slept and the shared spaces like the Lodge. The staff was amazing, with kind responses and quick to answer/help out with any questions we had. One of the best properties I’ve ever stayed at, and the people here make it the 5 Star quality that it is."
Bryn 1-night trip
Posted 16 hours ago
Urban Cowboy Lodge

Find out more about Windham

Windham Resorts information

Number of reviews
2,129
Accommodation
0 Resorts
Lowest Price
CA $191
Highest Price
CA $1,504

Frequently asked questions

What can I expect from a resort vacation in Windham?
You deserve some time off, and a resort is the ideal place to indulge in all the amenities and services you need for a relaxing stay in Windham. One of the comfortable resorts in the area could be just what you're looking for, whether you want great restaurants on site, shopping possibilities, or fun activities to try.
What can I do in Windham?
Travelers like the mountain scenery in Windham, and enjoy its skiing and other winter sports. Grab your golf clubs for a game at Windham Country Club, or head for the ski slopes at Windham Mountain Resort. For more to see in the area, you can spend time at Windham Vineyards and Winery or Catskill State Park.
What's the seasonal weather like in Windham?
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.
What's the best way to get to 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 venture out around the area, consider renting a car to take in more sights.

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