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Recommended hotels in Windham

1. Hotel Vienna

Hotel Vienna
3.0 star property
Windham
9.4 out of 10, Exceptional, (907 reviews)
"Clean room and helpful staff, good location."
United States
Hongtao
The price is CA $158
CA $195 total
includes taxes & fees
Nov 15 - Nov 16
Hotel Vienna

2. The Winwood Condominiums

The Winwood Condominiums
3.0 star property
Windham
8.8 out of 10, Excellent, (376 reviews)
"Loved it - cozy room, convenient location, beautiful view, and even breakfast offered :)"
United States
Zihe
The price is CA $237
CA $256 total
includes taxes & fees
Nov 8 - Nov 9
The Winwood Condominiums

3. 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 $244
CA $263 total
includes taxes & fees
Nov 8 - Nov 9
Albergo Allegria Hotel

4. 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 $208
CA $225 total
includes taxes & fees
Nov 12 - Nov 13
Jimmy OConnors Windham Mountain Inn

5. Wylder Hotel Windham

Wylder Hotel Windham
3.5 star property
Windham
9.0 out of 10, Wonderful, (136 reviews)
"Room super clean and beautiful property!"
United States
Daniela
The price is CA $305
CA $399 total
includes taxes & fees
Nov 29 - Nov 30
Wylder Hotel Windham

6. 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, (46 reviews)
"Great, highly recommend"
United States
Rebecca
The price is CA $95
CA $166 total
includes taxes & fees
Nov 8 - Nov 9
Studio 3 BEDS-SLP 3. Downtown Windham. Next to the Ski Resort. Close to Hunter

7. Cave Mountain Motel

Cave Mountain Motel
2.5 star property
Windham
9.4 out of 10, Exceptional, (152 reviews)
"the rooms were spotless. the owners were great. Had a wonderful stay"
United States
Nancy
The price is CA $195
CA $210 total
includes taxes & fees
Nov 9 - Nov 10
Cave Mountain Motel

8. 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 $324
CA $391 total
includes taxes & fees
Nov 15 - Nov 16
Eastwind Windham

9. 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 $189
CA $204 total
includes taxes & fees
Nov 12 - Nov 13
Antique Rose Inn Windham

10. The Haüs Windham

The Haüs Windham
2.0 star property
Windham
8.0 out of 10, Very good, (40 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 $204
CA $431 total
includes taxes & fees
Nov 9 - Nov 10
The Haüs Windham

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
8.8 out of 10, Excellent, (66 reviews)
"The pictures are not accurate. The two full and one twin bed are in one room upstairs, they are not separated as pictures would lead you to believe. Then three twins are in the living room with the couch, next to the dining room table and kitchen. The unit was dusty and not swept clean. There were dead bugs on the floor and party poppers from previous guest. I have never experienced something like this with Expedia, this was a zero star experience honestly."
United States
April
The price is CA $154
CA $260 total
includes taxes & fees
Nov 9 - Nov 10
TOWNHOUSE-Slp 8 Mt View/6 BEDS. Downtown Windham. Walk to restaurants and stores

12. 1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain

1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain
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 $208
CA $258 total
includes taxes & fees
Nov 9 - Nov 10
1BR Suite with Full Kitchen and Fireplace, 3 Min to Windham Mountain

13. 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 $255
CA $718 total
includes taxes & fees
Nov 11 - Nov 12
2 Min Walk to Windham Town | Hot Tub | Fire Pit

14. 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 $271
CA $722 total
includes taxes & fees
Nov 8 - Nov 9
Pines Vignette • Modern 3BR Home in Windham

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

Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome
Windham
9.0 out of 10, Wonderful, (9 reviews)
"We loved ,.. place was very clean and organized "
United States
Cristina L.
The price is CA $242
CA $686 total
includes taxes & fees
Nov 9 - Nov 10
Windham Mountain Slope-Side Escape w/ Private Hot Tub| Pets Welcome

16. 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
10.0 out of 10, Exceptional, (1 review)
"My stay was very short but we maximized our time by enjoying the properties endless offerings. Lots of things to do and board games were available. Plenty of room and beds every one. View from jacuzzi was phenomenal to see the stars at night. I’d recommend definitely and will revisit during winter"
United States
Lobid C.
The price is CA $301
CA $1,017 total
includes taxes & fees
Nov 8 - Nov 9
Large Chalet w/ Hot Tub, Fire Pit & 2 Living Rooms + Mins to Town & WMC

17. 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 $564
CA $901 total
includes taxes & fees
Nov 17 - Nov 18
Beautiful Windham Chalet 2 minutes to Town and the Mountain

18. Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain

Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain
Windham
7.8 out of 10, Good, (6 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 $356
CA $429 total
includes taxes & fees
Nov 12 - Nov 13
Secluded Glass Cabin for Two with Fire Pit and Sauna near Windham Mountain

19. 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 $284
CA $575 total
includes taxes & fees
Nov 8 - Nov 9
Tiny House on Walnut Grove

20. 5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn

5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn
Windham
The price is CA $510
CA $859 total
includes taxes & fees
Nov 10 - Nov 11
5BR Chalet Sleeps 12 with Jacuzzi, Sauna and Gym, 3 Min to Windham Mtn
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.

Learn more about Windham

Nestled in the Catskills, this mountain town transforms from a powdery ski paradise to a lush hiking haven with seasons. Visit Windham Mountain for thrilling slopes in winter or explore the scenic Rail Trail when summer's wildflowers frame perfect mountain views.

Two skiers on a snowy slope with a valley and mountains in the background.

Top reviews in Windham

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