Windham, NY

Travel Guide

A winding road through a forest with autumn foliage, a rocky cliff on the right, and a mountain in the background.
A canoe on a calm lake with a forested shoreline.
A river surrounded by autumn foliage.
A snowy ski slope with trees on either side and a view of the valley below.
Two skiers on a snowy slope with a valley and mountains in the background.
Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
The price is AED 413 per night from Nov 15 to Nov 16
AED 413
AED 510 total
15 Nov - 16 Nov
includes taxes & fees
Book a stay at this golf hotel in Windham. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Hotel Vienna
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
The price is AED 798 per night from Dec 2 to Dec 3
AED 798
AED 1,046 total
2 Dec - 3 Dec
includes taxes & fees
Stay at this hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country Club are located ...
9/10 Wonderful! (135 reviews)
"Room super clean and beautiful property!"

Reviewed on 2 November 2026

Wylder Hotel Windham
The Winwood Condominiums

The Winwood Condominiums

3 out of 5
5220 NY-23 Windham NY
The price is AED 621 per night from Nov 4 to Nov 5
AED 621
AED 670 total
4 Nov - 5 Nov
includes taxes & fees
Book a stay at this ski hotel in Windham. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Windham Mountain Resort and Windham Country ...
8.8/10 Excellent! (373 reviews)
"Very nice room."

Reviewed on 1 November 2026

The Winwood Condominiums
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.
Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts

Windham NY
Book a stay at this family-friendly vacation home in Windham. Enjoy a fitness center, a garden, and laundry facilities. Popular attractions Windham Mountain ...
10/10 Exceptional! (115 reviews)
"Very good rental"

Reviewed on 26 July 2026

Private Pickleball Ct - Indoor Hot Tub - Spa Room - Lift Tkts
Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain

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

Windham NY
Stay at this cabin in Windham. Enjoy a fitness center and a pool table. Popular attractions Windham Mountain Resort and Windham Country Club are located ...
7.6/10 Good! (5 reviews)
"The only complaint is they listed a hot tub showed it adjacent to the cabin in a photo and it fid not exist"

Reviewed on 7 September 2026

Secluded Glass Cabin in the Woods, 3 Minutes to Windham Mountain
Magical Home Located in Windham and Catskills

Magical Home Located in Windham and Catskills

Windham NY
Stay at this vacation home in Windham. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windham Mountain Resort and Ashland Park are located ...
9.8/10 Exceptional! (25 reviews)
"Beautiful property and central to Windham. Check in was a breeze and everything was well maintained."

Reviewed on 3 October 2026

Magical Home Located in Windham and Catskills
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.

Stay near popular Windham attractions