Title: Windsor Vacation Packages 2026 from $325 | 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 $325 ## 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. ![Comfort Suites Hartville - North Canton](https://images.trvl-media.com/lodging/12000000/11080000/11070600/11070507/88a664ec_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Suites Hartville - North Canton $325 per person May 14 - May 17 found 12 hours ago Roundtrip flight included Tampa (TPA) to Cleveland (CLE) 9.6/10 Exceptional! (1,000 reviews) Everything was amazing! Reviewed on Mar 30, 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 $776 per person Jun 6 - Jun 11 found 1 day ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 8.2/10 Very Good! (36 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 ![InterContinental Cleveland by IHG](https://images.trvl-media.com/lodging/1000000/920000/916400/916333/6d6c9251_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Cleveland by IHG Fairfax Save 100% on your flight $851 per person Jun 17 - Jun 23 found 11 hours ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 9/10 Wonderful! (872 reviews) All good except the mold/mildew in the shower Reviewed on Mar 2, 2026 ![InterContinental Suites Hotel Cleveland by IHG](https://images.trvl-media.com/lodging/1000000/430000/425000/424938/b33d2958_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Suites Hotel Cleveland by IHG Fairfax $748 per person Jun 17 - Jun 23 found 11 hours ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.8/10 Excellent! (1,005 reviews) Breakfast buffet was overpriced and mediocre at best. Bacon was swimming in grease and water. Eggs we runny and in water. Coffee in lobby was out one morning and missing cups and creamer out the next morning. Staff was very nice and helpful though Reviewed on Apr 5, 2026 ![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 $778 per person Jun 21 - Jun 24 found 16 hours ago Roundtrip flight included Newark Liberty Intl. Airport (EWR) to Cleveland (CLE) 9/10 Wonderful! (86 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 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/2026-05-06/2026-05-13/?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 12 - Apr 13 Total with taxes and fees 7.4/10 Good! (1,003 reviews) Internet sucks Reviewed on Apr 5, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%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 Apr 12 - Apr 13 Total with taxes and fees 9.2/10 Wonderful! (1,002 reviews) Wonderful, clean and quiet. Professional staff everywhere Reviewed on Apr 3, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F12%2F2026&endDate=4%2F13%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 $160 nightly $181 total Apr 15 - Apr 16 Total with taxes and fees 9.2/10 Wonderful! (842 reviews) Beautiful, lodge was very clean and staff was very friendly. Definitely will go back Reviewed on Mar 31, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F15%2F2026&endDate=4%2F16%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) [See all 575 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=4%2F7%2F2026&endDate=4%2F8%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.