Beautiful Fall colors

Book a Windham Resort

  • 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

Next weekend
Jun 26 - Jun 28
In two weeks
Jul 3 - Jul 5
In one month
Jul 17 - Jul 19
In two months
Aug 14 - Aug 16
No exact matches found, but these alternatives could be just right

Recommended hotels in Windham

View from room

Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (810 reviews)
"Great place"
United States
John
The price is ￥21,334
￥25,811 total
includes taxes & fees
Jul 1 - Jul 2
Hotel Vienna
Front of property

Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (143 reviews)
"Low key but very nice. Excellent location and value."
United States
Dan
The price is ￥20,842
￥22,509 total
includes taxes & fees
Jul 8 - Jul 9
Cave Mountain Motel
Interior

The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.6 out of 10, Good, (29 reviews)
"Can’t complain one bit"
United States
Christopher
The price is ￥20,668
￥35,300 total
includes taxes & fees
Jun 29 - Jun 30
The Haüs Windham
Double Room, Mountain View | Exterior

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
The price is ￥25,250
￥27,270 total
includes taxes & fees
Jun 21 - Jun 22
Jimmy OConnors Windham Mountain Inn
Front of property

Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (281 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
The price is ￥28,955
￥31,272 total
includes taxes & fees
Jun 21 - Jun 22
Albergo Allegria Hotel
Lushna Cabin | Free WiFi, bed sheets

Eastwind Windham

Eastwind Windham
3.5 star property
Windham
9.2 out of 10, Wonderful, (106 reviews)
"Everything about this stay was excellent! At check in Adriana made sure we had everything we needed and gave great recommendations for the area. The food at Dandies was so great that we ate there two out of the three nights of our stay. At the Dandies bar, Jaime and Andre were fun to talk to and very attentive. Room was spotless and decor was perfection. Grounds were gorgeous. Cannot wait to stay again!"
United States
Kristina
The price is ￥31,909
￥39,041 total
includes taxes & fees
Jul 15 - Jul 16
Eastwind Windham
Exterior

Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
8.8 out of 10, Excellent, (100 reviews)
"Beautiful property with lots to do!"
United States
Karen
The price is ￥36,793
￥47,753 total
includes taxes & fees
Jun 23 - Jun 24
Wylder Hotel Windham
Exterior

The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (354 reviews)
"It was so comfortable to stay there, we skied and was the perfect place to stay for a couple nights. "
United States
Nicoletta
The price is ￥21,946
￥23,703 total
includes taxes & fees
Jun 17 - Jun 18
The Winwood Condominiums
Exterior

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 ￥13,620
￥23,363 total
includes taxes & fees
Jun 17 - Jun 18
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
Exterior

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, (60 reviews)
"Good size space in a great location. Would definitely stay here again "
United States
Michael C.
The price is ￥20,831
￥34,612 total
includes taxes & fees
Jun 17 - Jun 18
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
Terrace/patio

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 ￥25,238
￥44,909 total
includes taxes & fees
Jun 17 - Jun 18
Tiny House on Walnut Grove
Classic Double Room, 1 King Bed with Sofa bed, Non Smoking | Iron/ironing board, free WiFi, bed sheets

The Outpost by Windham Mountain Club

The Outpost by Windham Mountain Club
2.5 star property
Windham
8.4 out of 10, Very Good, (5 reviews)
"Cozy and warm. I think it would be better to visit during the winter season"
United States
TAEJUN
The price is ￥72,108
￥77,877 total
includes taxes & fees
Jun 29 - Jun 30
The Outpost by Windham Mountain Club
Smart TV, fireplace

Spacious King Suite · Full Kitchen · Dining · Fireplace · Private Deck ·Sleeps 4

Spacious King Suite · Full Kitchen · Dining · Fireplace · Private Deck ·Sleeps 4
Windham
8.0 out of 10, Very Good, (2 reviews)
"This apartment is comfortable, clean and very good location. The hot tub is a plus with the beautiful view. "
United States
Evelyn
The price is ￥30,117
￥38,909 total
includes taxes & fees
Jun 24 - Jun 25
Spacious King Suite · Full Kitchen · Dining · Fireplace · Private Deck ·Sleeps 4
Exterior

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 ￥32,048
￥84,626 total
includes taxes & fees
Jul 7 - Jul 8
Pines Vignette • Modern 3BR Home in Windham
Dining

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 ￥32,048
￥86,876 total
includes taxes & fees
Jun 17 - Jun 18
2 Min Walk to Windham Town | Hot Tub | Fire Pit
TV, fireplace

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, (7 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is ￥31,888
￥84,626 total
includes taxes & fees
Jun 17 - Jun 18
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Hair dryer, towels, soap, shampoo

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn

Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
Windham
The price is ￥23,387
￥30,181 total
includes taxes & fees
Jun 17 - Jun 18
Cozy Boutique Suite · 2 Full Beds · Spa Bathroom · 3 Min to Windham Mtn
In-room safe, bed sheets

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway

Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
Windham
8.0 out of 10, Very Good, (2 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 ￥47,912
￥60,797 total
includes taxes & fees
Jun 22 - Jun 23
Iconic Glass Mirror Cabin · Forest View · Private Fire Pit · Catskills Hideaway
Exterior

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC

Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Windham
The price is ￥39,249
￥106,941 total
includes taxes & fees
Jul 13 - Jul 14
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
Interior

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!

Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
Ashland
9.2 out of 10, Wonderful, (5 reviews)
"Great place to stay very accommodating more than expected "
United States
Julia M.
The price is ￥56,084
￥87,741 total
includes taxes & fees
Jun 22 - Jun 23
Ski retreat near Hunter and Windham. Mountain views! Family and pet friendly!
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Windham Hotel Reviews

Hunter Lodge, a Bluebird by Lark

Hunter Lodge, a Bluebird by Lark

10/10 Excellent
"Very nice & clean, Hunter tavern was yummy, nice fire pits Hunter Mountain couple miles down the road"
Joanne 2-night trip
Posted 6 hours ago
Hunter Lodge, a Bluebird by Lark

Find out more about Windham

Windham Resorts information

Number of reviews
Accommodation
 Resorts
Lowest Price
Highest Price

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 Catskill State Park or Windham Vineyards and Winery.
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.

Explore a world of travel with Expedia