Title: Windsor Vacation Packages 2026 from $275 | 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 $275 ## Book a Hotel + Flight or Car together to unlock savings ## 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. ![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 Save 100% on your flight $275 per person May 7 - May 9 found 23 hours ago Roundtrip flight included Atlanta (ATL) to Cleveland (CLE) 8.6/10 Excellent! (2,084 reviews) Great experience will definately book again Reviewed on Mar 16, 2026 ![The Inn at Fulton](https://images.trvl-media.com/lodging/103000000/102660000/102658400/102658389/2099735d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Inn at Fulton Save 100% on your flight $693 per person Jun 2 - Jun 6 found 1 day ago Roundtrip non-stop flight included San Juan (SJU) to Cleveland (CLE) 8/10 Very Good! (35 reviews) Looked just like the pictures. Very clean. Only thing i would say is it only had one bathroom and that bathroom is located inside the master room so the other guest had to come in that room to use the bathroom so just be prepared for that. Other than that loved the area and place. Reviewed on Dec 27, 2025 ![Kimpton Schofield Hotel by IHG](https://images.trvl-media.com/lodging/14000000/13190000/13181300/13181279/ba15d366_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Kimpton Schofield Hotel by IHG Downtown Cleveland $557 per person Jun 5 - Jun 7 found 24 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Cleveland (CLE) 8.8/10 Excellent! (1,026 reviews) Stayed for two nights. Overall a good option when staying in downtown Cleveland. Close to most things downtown Cleveland. People at the front desk, while knowledgeable, can be a little more people friendly. The room was good overall. Would stay again. Reviewed on Mar 19, 2026 ![Hilton Garden Inn Cleveland Downtown](https://images.trvl-media.com/lodging/1000000/870000/866100/866043/2d490d61_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hilton Garden Inn Cleveland Downtown Downtown Cleveland $545 per person Jun 5 - Jun 7 found 24 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Cleveland (CLE) 7.6/10 Good! (1,008 reviews) Clean. Good location, good people. The breakfast was great and the service was excellent Reviewed on Mar 16, 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/2026-04-19/2026-04-26/?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 ![Red Roof Inn Cleveland - Mentor/ Willoughby](https://images.trvl-media.com/lodging/1000000/20000/13800/13716/7c09b76c_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 $61 nightly $70 total Apr 1 - Apr 2 Total with taxes and fees 7.4/10 Good! (1,001 reviews) Can't expect much from a cheap motel like this. Bed was comfortable. But 2nd floor with no elevator access makes it hard when you are partially handicapped. Parking plentiful but was concerned about car safety, so I had to bring everything from the car into my room which was very small. Not business ... Reviewed on Mar 10, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F1%2F2026&endDate=4%2F2%2F2026&selected=13716&PinnedHotelID=13716&HadPinnedHotel=true®ionId=6180248) ![Best Western Plus Mentor-Cleveland Northeast](https://images.trvl-media.com/lodging/1000000/660000/660000/659951/6708ea96_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 $96 nightly $111 total Mar 24 - Mar 25 Total with taxes and fees 9.2/10 Wonderful! (1,000 reviews) The staff was welcoming and helpful. Breakfast was excellent Room very clean, and bed comfortable. Definitely would stay there again Reviewed on Mar 9, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F24%2F2026&endDate=3%2F25%2F2026&selected=659951&PinnedHotelID=659951&HadPinnedHotel=true®ionId=6180248) ![The Lodge at Geneva](https://images.trvl-media.com/lodging/2000000/1380000/1372100/1372060/16d56c9d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Lodge at Geneva 4888 N. Broadway Geneva OH Fully refundableReserve now, pay when you stay $122 nightly $138 total Mar 23 - Mar 24 Total with taxes and fees 9.2/10 Wonderful! (835 reviews) The staff was great. Very clean and quiet. The pool and hot tub was amazing. We will return. Reviewed on Mar 15, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F23%2F2026&endDate=3%2F24%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) [See all 569 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F20%2F2026&endDate=3%2F21%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.