Title: Windsor Vacation Packages 2026 from $366 | 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 $366 ## 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. ![ Explorer Rest & Recreation](https://images.trvl-media.com/lodging/97000000/96470000/96462400/96462346/270560aa_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Explorer Rest & Recreation $366 per person Jun 1 - Jun 5 found 1 day ago Roundtrip flight included Atlanta (ATL) to Cleveland (CLE) 9.2/10 Wonderful! (344 reviews) Very clean and a great rate. Tons of space and comfortable. Only complaint, lack of hot water for showers. Would stay again Reviewed on Mar 5, 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 $517 per person Jun 1 - Jun 5 found 1 day ago Roundtrip flight included Atlanta (ATL) 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 ![The Washington Boutique Hotel](https://images.trvl-media.com/lodging/100000000/99990000/99982700/99982661/391bcf5c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Washington Boutique Hotel Save 100% on your flight $773 per person Jun 1 - Jun 5 found 1 day ago Roundtrip flight included Atlanta (ATL) to Cleveland (CLE) 9/10 Wonderful! (85 reviews) Room was clean and cute decor, there is no staff, more like an air bnb….and there is no parking. There a small parking lot on the s Reviewed on Mar 11, 2026 ![Anchor Bay Inn and Suites](https://images.trvl-media.com/lodging/85000000/84090000/84083600/84083550/d23dc7eb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Anchor Bay Inn and Suites Save 100% on your flight $406 per person Jun 1 - Jun 5 found 1 day ago Roundtrip flight included Atlanta (ATL) to Cleveland (CLE) 8.8/10 Excellent! (160 reviews) Room was very clean but the heat/ Reviewed on Oct 29, 2025 ![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 $536 per person Jun 7 - Jun 10 found 23 hours ago Roundtrip flight included New York (NYC) 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/2026-04-21/2026-04-28/?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 5/5(3 reviews) 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! (1,002 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 $101 nightly $117 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 $128 nightly $145 total Mar 24 - Mar 25 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%2F24%2F2026&endDate=3%2F25%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) [See all 566 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F22%2F2026&endDate=3%2F23%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