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

Best Resorts in Windham

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Check prices for these dates

Next weekend
Sep 4 - Sep 6
In two weeks
Sep 11 - Sep 13
In one month
Sep 25 - Sep 27
In two months
Oct 23 - Oct 25
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, (857 reviews)
"Was just amazing! Everyone one so friendly and the place and area is very picturesque!"
United States
Ruben
$161 nightly
The price is $174
Sep 2 - Sep 3
Total with taxes and fees
Hotel Vienna
A rustic stone building with a sign for Windham Mountain Inn, surrounded by autumn foliage.

2. Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn
Windham
8.6 out of 10, Excellent, (4 reviews)
"What a gem of a property! The brother and sister that own and operate this place are so sweet and hospitable, and the bar and motel are quaint and charming in a cozy, woodsy way. If I’m ever in the area I would absolutely stay here again."
United States
Amy
$135 nightly
The price is $146
Sep 29 - Sep 30
Total with taxes and fees
Jimmy OConnors Windham Mountain Inn
A two-story building with a balcony, surrounded by well-maintained lawns and trees.

3. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (363 reviews)
"Great place for a couple."
United States
Abdul
$167 nightly
The price is $180
Sep 2 - Sep 3
Total with taxes and fees
The Winwood Condominiums
A large, multi-story house with a wrap-around porch and a small tower-like structure on the roof.

4. Antique Rose Inn Windham

Antique Rose Inn Windham
3.0 star property
Windham
9.0 out of 10, Wonderful, (136 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Sep 1 - Sep 2
Total with taxes and fees
Antique Rose Inn Windham
A bedroom with a large window, a bed, and a view of a forest.

5. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
7.8 out of 10, Good, (34 reviews)
"Firstly I would like to say communication with the staff is extremely difficult. Constantly having to call multiple times to get to someone. For example, the code given for room wasn’t correct and communication took forever. There was no toiletries whatsoever and since communication was so hard it forced us to buy our own paper towels, towels, rags, etc. The property was nice but it was clear no housekeeping had been in there before we came. The nature was probably the only thing that made up...
United States
Raven Jane
$260 nightly
The price is $281
Sep 30 - Oct 1
Total with taxes and fees
The Haüs Windham
A large, two-story house with multiple porches and string lights.

6. Albergo Allegria Hotel

Albergo Allegria Hotel
3.5 star property
Windham
9.6 out of 10, Exceptional, (285 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Aug 31 - Sep 1
Total with taxes and fees
Albergo Allegria Hotel
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, (116 reviews)
"The staff was friendly and the room was clean and comfortable. Would love to come back again!"
United States
Claire
$319 nightly
The price is $344
Aug 31 - Sep 1
Total with taxes and fees
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
8.8 out of 10, Excellent, (120 reviews)
"Elodie was an absolute angel!! So accommodating and helpful in everywhere. It was my second time visiting and will definitely be back again"
United States
Shardei
$315 nightly
The price is $341
Aug 31 - Sep 1
Total with taxes and fees
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.
$135 nightly
The price is $146
Sep 2 - Sep 3
Total with taxes and fees
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter
A two-story building with large windows and a storefront.

10. 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, (63 reviews)
"Overall great experience. Very central location. Host lives in building, so is always available. They grow tomato's and cucumbers on the balcony that they invited us to "take as much as you want" My only discomfort with this place was the dust and dirty dishes. The people before us half-washed the things they used and the place seemed like it needed a pass with a vacuum cleaner. The floors were not very clean. In general, I greatly enjoyed my stay here."
United States
David
$205 nightly
The price is $221
Aug 31 - Sep 1
Total with taxes and fees
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores
A kitchen with green cabinets, a stainless steel stove, and a brick wall.

11. NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham

NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
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.
$178 nightly
The price is $203
Aug 31 - Sep 1
Total with taxes and fees
NEW OUTDOOR HOT TUB! 1-Bedroom Luxury Suite + Full Kitch - Haus Windham
A large, two-story house with a stone facade, a wooden deck, and a clear sky.

12. 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
$529 nightly
The price is $572
Sep 1 - Sep 2
Total with taxes and fees
Hot Tub, Fire pit, Fireplace - Large Chalet Just Minutes to Town + WMC
A spacious living area with a wooden dining table, a sofa, a fireplace, and a view of the outdoors.

13. 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.
$505 nightly
The price is $545
Sep 23 - Sep 24
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
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.
$488 nightly
The price is $527
Sep 23 - Sep 24
Total with taxes and fees
2 Min Walk to Windham Town | Hot Tub | Fire Pit
A modern bedroom with a large bed, a dining table, and a view of a forest through large windows.

15. MIRROR CABIN IN THE FOREST WITH HOT TUB

MIRROR CABIN IN THE FOREST WITH HOT TUB
Windham
8.0 out of 10, Very Good, (4 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.
$251 nightly
The price is $285
Sep 21 - Sep 22
Total with taxes and fees
MIRROR CABIN IN THE FOREST WITH HOT TUB
A two-story cabin with a balcony and a chimney, surrounded by a snowy forest.

16. 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.
$503 nightly
The price is $543
Sep 9 - Sep 10
Total with taxes and fees
Pines Vignette • Modern 3BR Home in Windham

17. Cozy 1-bedroom studio in peaceful Ashland with AC

Cozy 1-bedroom studio in peaceful Ashland with AC
Ashland
$326 nightly
The price is $352
Sep 1 - Sep 2
Total with taxes and fees
Cozy 1-bedroom studio in peaceful Ashland with AC
A cozy living room with wooden walls, a stone fireplace, and a television.

18. 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.
$631 nightly
The price is $682
Sep 8 - Sep 9
Total with taxes and fees
Beautiful Windham Chalet 2 minutes to Town and the Mountain
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.

19. 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
10.0 out of 10, Exceptional, (1 review)
"Host had an amazing response time. Very easy to talk with via email. She had very clear and easy instructions on check in and check out. The place had lots of bedding, it was warm and inviting, had everything we needed. My daughter thought the “balcony” on the second floor which over looked the kitchen was cool! "
United States
Soonae S.
$609 nightly
The price is $658
Aug 31 - Sep 1
Total with taxes and fees
Charming 2-bedroom townhome in lovely Windham Mountain Village. Walk to skiing.
A fire pit with two chairs in a backyard.

20. NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM

NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
Windham
$566 nightly
The price is $622
Aug 31 - Sep 1
Total with taxes and fees
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
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

AutoCamp Catskills

AutoCamp Catskills

10/10 Excellent
"No comment"
Ryan 2-night trip
Posted 11 hours ago
AutoCamp Catskills

Find out more about Windham

Windham Resorts information

Number of reviews
1,023
Accommodation
0 Resorts
Lowest Price
$146
Highest Price
$682

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.

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