Title: Windham Vacation Packages & Trips 2026 | Expedia.ca [Windham Travel Guide](https://expedia.ca/Windham.dx175529)[Hotels in Windham](https://expedia.ca/Windham-Hotels.d175529.Travel-Guide-Hotels)[Vacation Rentals in Windham](https://expedia.ca/Windham-Vacation-Rentals.d175529.Travel-Guide-VacationRentals)[Flights to Windham](https://expedia.ca/Cheap-Flights-To-Windham.d175529.Travel-Guide-Flights)[Things to do in Windham](https://expedia.ca/Things-To-Do-In-Windham.d175529.Travel-Guide-Activities)[Windham Car Rentals](https://expedia.ca/Car-Rentals-In-Windham.d175529.Car-Rental-Guide) ![](https://images.trvl-media.com/place/175529/3d9b5210-4eb0-422c-87cb-eedcfc9fa09e.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windham Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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](https://images.trvl-media.com/lodging/1000000/900000/893300/893228/75609405_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hotel Vienna 107 State Route 296 Windham NY 9.2/10 Wonderful! (717 reviews) Love this place when its available. Low key, clean and conveniently near BOTH Hunter and Windham ski areas! Reviewed on Dec 8, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=893228&PinnedHotelID=893228&HadPinnedHotel=true®ionId=175529) [](https://expedia.ca/Hotel-Search?startDate=30%2F12%2F2025&endDate=31%2F12%2F2025&selected=893228&PinnedHotelID=893228&HadPinnedHotel=true®ionId=175529) ![Eastwind Windham](https://images.trvl-media.com/lodging/92000000/91910000/91907200/91907167/6052e62a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Eastwind Windham 5088 NY-23 Windham NY CA $382 CA $456 total Dec 21 - Dec 22 includes taxes & fees 9.2/10 Wonderful! (73 reviews) This is an awesome hotel, especially if you can properly dedicate some time to leveraging its amenities. It's also super unique. Whenever i come here, I always wish I could stay longer, even if, provided you're staying at a kushna, you'll have to acclimate a bit to dashing in the cold between your ... Reviewed on Dec 10, 2025 [](https://expedia.ca/Hotel-Search?startDate=21%2F12%2F2025&endDate=22%2F12%2F2025&selected=91907167&PinnedHotelID=91907167&HadPinnedHotel=true®ionId=175529) ![Wylder Hotel Windham](https://images.trvl-media.com/lodging/103000000/102240000/102239500/102239431/247f19f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Wylder Hotel Windham 19 New York 296 Windham NY CA $283 CA $375 total Dec 17 - Dec 18 includes taxes & fees 8.6/10 Excellent! (89 reviews) Beautiful mountain view, my daughter loves the sauna barrel! The only thing is they do not have a microwave inside of the room. Reviewed on Nov 30, 2025 [](https://expedia.ca/Hotel-Search?startDate=17%2F12%2F2025&endDate=18%2F12%2F2025&selected=102239431&PinnedHotelID=102239431&HadPinnedHotel=true®ionId=175529) [See all 2,096 properties in Windham](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=17%2F12%2F2025&endDate=18%2F12%2F2025®ionId=175529) 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. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ### Discover the most popular places to visit in Windham #### Windham Mountain Resort Hit the slopes in Windham with a visit to Windham Mountain Resort. Discover the mountain views in this relaxing area. [](https://expedia.ca/Windham-Mountain-Resort-Windham.d6087209.Vacation-Attraction) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app