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

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22
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, (876 reviews)
"Clean quiet breakfast was amazing"
United States
john
$145 nightly
The price is $157
Oct 1 - Oct 2
Total with taxes and fees
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, (364 reviews)
"Great place for a couple."
United States
Abdul
$167 nightly
The price is $180
Sep 28 - Sep 29
Total with taxes and fees
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
9.4 out of 10, Exceptional, (9 reviews)
"The staff was super friendly and helpful. Mel took great care of us at the bar and got us checked in smoothly. She was happy to help us with local shopping and events. We will definitely come back next year!!! :-)"
United States
James
$149 nightly
The price is $160
Oct 6 - Oct 7
Total with taxes and fees
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, (286 reviews)
"Amazing hotel, very clean and comfortable beds."
United States
Roy
$174 nightly
The price is $188
Sep 23 - Sep 24
Total with taxes and fees
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, (149 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
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, (137 reviews)
"A fantastic stay!"
United States
David
$135 nightly
The price is $146
Sep 23 - Sep 24
Total with taxes and fees
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, (118 reviews)
"The cabin was adorable, everything at Dandies was delicious and Jamie was extremely helpful"
United States
Sharon
$319 nightly
The price is $344
Sep 23 - Sep 24
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, (128 reviews)
"Wonderful stay"
United States
Yousung
$347 nightly
The price is $374
Sep 24 - Sep 25
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.
$127 nightly
The price is $137
Sep 23 - Sep 24
Total with taxes and fees
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
7.8 out of 10, Good, (35 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
$282 nightly
The price is $305
Oct 7 - Oct 8
Total with taxes and fees
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)
"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
$237 nightly
The price is $256
Sep 24 - Sep 25
Total with taxes and fees
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.
$463 nightly
The price is $500
Sep 23 - Sep 24
Total with taxes and fees
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
A kitchen with green cabinets, a stainless steel stove, and a microwave.

13. 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.
$176 nightly
The price is $201
Sep 23 - Sep 24
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.

14. Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
Windham
$522 nightly
The price is $564
Sep 23 - Sep 24
Total with taxes and fees
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC
A dining area with a wooden table, six chairs, a chandelier, and a wall-mounted shelf.

15. 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.
$500 nightly
The price is $540
Sep 24 - Sep 25
Total with taxes and fees
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.

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.
$496 nightly
The price is $536
Sep 23 - Sep 24
Total with taxes and fees
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.

17. MIRROR CABIN IN THE FOREST WITH HOT TUB

MIRROR CABIN IN THE FOREST WITH HOT TUB
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.
$237 nightly
The price is $270
Oct 6 - Oct 7
Total with taxes and fees
MIRROR CABIN IN THE FOREST WITH HOT TUB
A pool area with a 'NO DIVING' sign, wooden benches, and stone walls.

18. 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.
$606 nightly
The price is $654
Sep 23 - Sep 24
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.

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

NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
Windham
$563 nightly
The price is $619
Sep 23 - Sep 24
Total with taxes and fees
NEW OUTDOOR HOT TUB!! 5 BEDROOM/3 BATH CHALET - HAUS WINDHAM
A cozy living room with a stone fireplace, a large sectional sofa, a round coffee table, and a wooden ceiling with a loft area.

20. Condo in Windham Mountain Village

Condo in Windham Mountain Village
Windham
10.0 out of 10, Exceptional, (16 reviews)
"Location is great"
United States
Jennifer M.
$733 nightly
The price is $792
Sep 23 - Sep 24
Total with taxes and fees
Condo in Windham Mountain Village
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

Jimmy OConnors Windham Mountain Inn

Jimmy OConnors Windham Mountain Inn

10/10 Excellent
"Cool little spot with the inn at the back of the property and the restaurant at the front. It’s been passed down through the family and I met the owner inside during a quick dinner, down to earth guy. The room is very vey clean and still sporting the original textures and fixtures, real retro feeling, I loved it."
Christopher 2-night trip
Posted 18 hours ago
Jimmy OConnors Windham Mountain Inn

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 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.

Explore a world of travel with Expedia