Name: Eastwind Windham
Price range: CA $282
Rating: 9.2

Plan, book, travel with confidence
Better together
Save up to CA $4,200 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place

Ready to book your vacation to Windham?

Choose your dates

Windham Hotel Deals

Hotel Vienna

107 State Route 296 Windham NY

CA $188

CA $228 total

Jul 1 - Jul 2

includes taxes & fees

9.4/10 Exceptional! (815 reviews)

"The access to the Windam Path was great. It is a lovely, easy walk by a stream and through meadows."

Reviewed on Jun 19, 2026

Wylder Hotel Windham

19 New York 296 Windham NY

CA $311

CA $407 total

Jun 25 - Jun 26

includes taxes & fees

8.8/10 Excellent! (100 reviews)

"Beautiful and spacious balcony overlooking the mountains and golf course. We loved the view from our room 521. . Great place to relax before dinner with a glass of wine/cheese. Location is good within walking distance to a most wonderful restaurant named prominence. Highly recommend. The on site ..."

Reviewed on Jun 15, 2026

Eastwind Windham

5088 NY-23 Windham NY

CA $282

CA $345 total

Jun 28 - Jun 29

includes taxes & fees

9.2/10 Wonderful! (107 reviews)

"Beautiful location. Really loved the full window ceiling in the cabin’s shower!"

Reviewed on Jun 19, 2026

See all 2,156 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.