
Windham Vacation Packages
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Save up to CA $1,096 when you book a flight and hotel together*
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Windham Hotel Deals

Hotel Vienna
107 State Route 296, Windham, NY
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from Sep 8 to Sep 9
CA $179
CA $193 total
Sep 8 - Sep 9
includes taxes & fees
9.2/10 Wonderful! (616 reviews)
"Great hotel"
Reviewed on Aug. 12, 2025

Eastwind Windham
5088 NY-23, Windham, NY
The price is CA $275 per night from Aug 19 to Aug 20
CA $275
CA $307 total
Aug 19 - Aug 20
includes taxes & fees
9.2/10 Wonderful! (58 reviews)
"Friendly staff, accommodating and clean Some of it under construction"
Reviewed on May 23, 2025

Wylder Hotel Windham
19 New York 296, Windham, NY
The price is CA $263 per night from Aug 19 to Aug 20
CA $263
CA $353 total
Aug 19 - Aug 20
includes taxes & fees
8.6/10 Excellent! (67 reviews)
"We LOVED staying at Wylder. The staff was super friendly and helpful. Our room was comfortable, views were amazing and we really enjoyed the amenities. Highly recommend!"
Reviewed on Jul. 21, 2025
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.
Discover the most popular places to visit in Windham
Windham Mountain Resort
5/5(2 reviews)
Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area.
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.