Title: Windsor Vacation Packages 2026 from $425 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx6180248)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d6180248.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d6180248.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d6180248.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d6180248.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6046880/887631b2-e098-411d-ad6d-5a87b7d10913.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacations from $425 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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 ## Your Windsor Vacation When you book a Windsor vacation package, you can relax and enjoy your adventure to the fullest. Uncover the highlights of this fascinating city knowing that all your travel needs have been taken care of before you go. During your trip to Windsor, carve some time in your schedule for sightseeing. A popular place to start exploring is [Windsor Mills Covered Bridge](https://www.expedia.com/Windsor-Mills-Covered-Bridge-Windsor.d6180252.Vacation-Attraction). Don't put off your visit to this destination any longer. The perfect Windsor vacation is a couple of clicks away with Expedia. ## The Latest Windsor vacation packages Price found within the past 48 hours. Click for updated prices. ![Hilton Garden Inn Cleveland Downtown](https://images.trvl-media.com/lodging/1000000/870000/866100/866043/725ce971_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Cleveland Downtown Downtown Cleveland $425 per person Apr 24 - Apr 27 found 19 hours ago Roundtrip flight included Denver (DEN) to Cleveland (CLE) 7.4/10 Good! (1,004 reviews) The staff were extremely friendly and helpful The room was clean and quiet. We will stay here again when we are in town. Reviewed on Feb 2, 2026 ![JARVIS Edgewater Park & Beach 5BD Villa](https://images.trvl-media.com/lodging/21000000/20160000/20156300/20156283/6844f8e7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### JARVIS Edgewater Park & Beach 5BD Villa Edgewater Save 100% on your flight $2,414 per person Mar 29 - Mar 31 found 20 hours ago Roundtrip non-stop flight included Newark Liberty Intl. Airport (EWR) to Cleveland (CLE) No reviews ![Kimpton Schofield Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13190000/13181300/13181279/db78d7b4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Schofield Hotel by IHG Downtown Cleveland $581 per person Apr 24 - Apr 27 found 19 hours ago Roundtrip flight included Denver (DEN) to Cleveland (CLE) 8.6/10 Excellent! (1,006 reviews) Staff was nice. But we were expecting the room to be equipped with more amenities and some snacks etc. Reviewed on Feb 4, 2026 ![InterContinental Cleveland by IHG](https://images.trvl-media.com/lodging/1000000/920000/916400/916333/6d8a0475_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Cleveland by IHG Fairfax $586 per person Apr 24 - Apr 27 found 19 hours ago Roundtrip flight included Denver (DEN) to Cleveland (CLE) 9/10 Wonderful! (843 reviews) Nice room, restaurants on site and convenient to Cleveland Clinic! Highly recommended! Reviewed on Jan 20, 2026 ![The Westin Cleveland Downtown](https://images.trvl-media.com/lodging/1000000/10000/3400/3332/a3be6d16_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Westin Cleveland Downtown Downtown Cleveland $460 per person Mar 7 - Mar 9 found 1 day ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Cleveland (CLE) 8.6/10 Excellent! (1,771 reviews) Room was very clean. Staff were very nice. Reviewed on Jan 30, 2026 Don't see what you're looking for? See all available trips from Columbus to Windsor [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-05/2026-03-12/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CGF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ### Discover the most popular places to visit in Windsor #### Windsor Mills Covered Bridge Learn about the local history of Windsor when you take a trip to Windsor Mills Covered Bridge. Experience the area's festivals and entertainment venues. [](https://expedia.com/Windsor-Mills-Covered-Bridge-Windsor.d6180252.Vacation-Attraction) ## Windsor Hotel Deals ![The Lodge at Geneva](https://images.trvl-media.com/lodging/2000000/1380000/1372100/1372060/6c62a377_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Lodge at Geneva 4888 N. Broadway Geneva OH Fully refundableReserve now, pay when you stay $123 nightly $140 total Feb 16 - Feb 17 Total with taxes and fees 9.2/10 Wonderful! (820 reviews) Everyone was very nice it was a beautiful place and I will be back. A home away from home!! Reviewed on Jan 24, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F16%2F2026&endDate=2%2F17%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) ![Red Roof Inn Cleveland - Mentor/ Willoughby](https://images.trvl-media.com/lodging/1000000/20000/13800/13716/dc1ee235_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Red Roof Inn Cleveland - Mentor/ Willoughby 4166 State Route 306 Willoughby OH Fully refundableReserve now, pay when you stay $57 nightly $65 total Feb 9 - Feb 10 Total with taxes and fees 7.2/10 Good! (1,000 reviews) They do still need to work on locks on door. First door key given didn’t work. Bathroom floor could have used a touch more love. Other than that all was fine. Reviewed on Dec 31, 2025 [](https://expedia.com/Hotel-Search?startDate=2%2F9%2F2026&endDate=2%2F10%2F2026&selected=13716&PinnedHotelID=13716&HadPinnedHotel=true®ionId=6180248) ![Best Western Plus Mentor-Cleveland Northeast](https://images.trvl-media.com/lodging/1000000/660000/660000/659951/ae24b750_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Plus Mentor-Cleveland Northeast 8434 Mentor Avenue Mentor OH Fully refundableReserve now, pay when you stay $93 nightly $107 total Feb 8 - Feb 9 Total with taxes and fees 9/10 Wonderful! (1,004 reviews) Staff polite, clean room, breakfast, coffee maker & supplies in room, small deposit held at arrival, large room. Uncomfortable mattress. Reviewed on Feb 4, 2026 [](https://expedia.com/Hotel-Search?startDate=2%2F8%2F2026&endDate=2%2F9%2F2026&selected=659951&PinnedHotelID=659951&HadPinnedHotel=true®ionId=6180248) [See all 559 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F6%2F2026&endDate=2%2F7%2F2026®ionId=6180248) 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. ## Find the Best Windsor Vacation Packages ## Windsor Essential Information | Language | English | | --------------- | ------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------ | | Currency | U.S dollars | | Max Temp Winter | 30ºF | | Max Temp Summer | 80ºF | | Top Sights | [Riverdale Road Covered Bridge](https://www.expedia.com/Riverdale-Road-Covered-Bridge-Rock-Creek.d6180212.Vacation-Attraction) and [Windsor Mills Covered Bridge](https://www.expedia.com/Windsor-Mills-Covered-Bridge-Windsor.d6180252.Vacation-Attraction) | ## More vacations you might like ![](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 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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 even more - get up to 20% on select hotels 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