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.
Aluminum canoe on a mountain lake upstate New York. Camping. outdoors and adventure concept. Faded, vintage color post processed
Amazing foliage upstate New York. Morning sunlight spills over the golden foliage. Windham NY is one of the most popular destination for scenic drives, bike trails, foliage and nature lovers.
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.
Wylder Hotel Windham

Wylder Hotel Windham

3.5 out of 5
19 New York 296 Windham NY
$303 nightly
The price is $327 total per night from Aug 23 to Aug 24
$327 total
Aug 23 - Aug 24
Total with taxes and 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 ...
8.8/10 Excellent! (115 reviews)
"The staff were wonderful and went out of their way to make sure you had whatever you wanted. There are plenty of things to do right at the hotel and you are right by the mountains if you want to take advantage of that. The pool is heated and you can have drinks by the pool. There are several locations ..."

Reviewed on Aug 9, 2026

Wylder Hotel Windham
Hotel Vienna

Hotel Vienna

3 out of 5
107 State Route 296 Windham NY
$164 nightly
The price is $177 total per night from Sep 7 to Sep 8
$177 total
Sep 7 - Sep 8
Total with taxes and 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
Eastwind Windham

Eastwind Windham

3.5 out of 5
5088 NY-23 Windham NY
$228 nightly
The price is $246 total per night from Aug 17 to Aug 18
$246 total
Aug 17 - Aug 18
Total with taxes and fees
Book a stay at this golf hotel in Windham. Enjoy free WiFi, free parking, and 2 bars/lounges. Popular attractions Windham Mountain Resort and Windham Country ...
Eastwind Windham
See all 2,148 properties in 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.
Woodside Cabin #2 on Lake Heloise

Woodside Cabin #2 on Lake Heloise

Windham NY
Stay at this cabin in Windham. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Windham Mountain Resort and Elm Ridge Wild Forest ...
9.4/10 Exceptional! (16 reviews)
"If you're looking for a cozy cabin in a quiet, picturesque setting, definitely go here. It has everything you need for a quiet, relaxing getaway...including a hot tub. We just returned but will definitely be going back. And the dogs loved it too!"

Reviewed on Jul 23, 2026

Woodside Cabin #2 on Lake Heloise
Lake view Cabin on Lake Heloise

Lake view Cabin on Lake Heloise

Windham NY
Stay at this cabin in Windham. Enjoy air conditioning and a hot tub. Popular attractions Windham Mountain Resort and Elm Ridge Wild Forest are located ...
10/10 Exceptional! (19 reviews)
"As described. Beautiful & serene view. 100% pet friendly. Would go again."

Reviewed on Aug 13, 2026

Lake view Cabin on Lake Heloise
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! (22 reviews)
"Very nice house"

Reviewed on Aug 3, 2026

Magical Home Located in Windham and Catskills
See all properties in 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.

Stay near popular Windham attractions

Windham Mountain Resort

9.0/10 (313 reviews)
Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area.
See properties

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