Title: Windsor Vacation Packages 2026 from $414 | 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 $414 ## 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 $414 per person Apr 24 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 7.4/10 Good! (1,004 reviews) Very helpful staff! We enjoyed the poo Reviewed on Feb 17, 2026 ![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 $538 per person Apr 24 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.6/10 Excellent! (1,006 reviews) Everything was great Reviewed on Feb 24, 2026 ![Comfort Inn Mayfield Heights Cleveland East](https://images.trvl-media.com/lodging/1000000/50000/49700/49650/fcd3a986_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Comfort Inn Mayfield Heights Cleveland East $506 per person May 6 - May 10 found 1 day ago Roundtrip flight included Phoenix (PHX) to Cleveland (CLE) 8.2/10 Very Good! (1,000 reviews) The morning front desk guy was very friendly and helpful. The breakfast was very average. The room was clean. The main problem we had was the hall and elevator always had a strong smoke smell of pot. My husband is very allergic to smoke and it a non smoking hotel everywhere. That was our biggest disappointment. Reviewed on Feb 23, 2026 ![Courtyard by Marriott Cleveland Willoughby](https://images.trvl-media.com/lodging/1000000/290000/280900/280889/1390a7a6_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Cleveland Willoughby $439 per person May 6 - May 10 found 1 day ago Roundtrip flight included Phoenix (PHX) to Cleveland (CLE) 8.4/10 Very Good! (717 reviews) Clean room, all new. Great dining options Reviewed on Feb 8, 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 $446 per person Apr 24 - Apr 27 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.6/10 Excellent! (1,771 reviews) Staff was pleasant and room was clean. Reviewed on Feb 26, 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/2026-03-27/2026-04-03/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=CGF&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_6180248) ### 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 ![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 $98 nightly $112 total Mar 15 - Mar 16 Total with taxes and fees 9.2/10 Wonderful! (1,000 reviews) Room was magnicent. Staff was great Reviewed on Feb 21, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=659951&PinnedHotelID=659951&HadPinnedHotel=true®ionId=6180248) ![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 Mar 3 - Mar 4 Total with taxes and fees 9.2/10 Wonderful! (827 reviews) Location and water view were excellent. Rooms clean and roomy.. Reviewed on Feb 22, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%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 $55 nightly $64 total Mar 3 - Mar 4 Total with taxes and fees 7.4/10 Good! (1,002 reviews) The staff were good. It served our needs. Our only complaint was that it was supposed to be a non smoking room and it smelled of smoke so badly I did not have a good night's sleep Reviewed on Feb 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F3%2F2026&endDate=3%2F4%2F2026&selected=13716&PinnedHotelID=13716&HadPinnedHotel=true®ionId=6180248) [See all 560 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F28%2F2026&endDate=3%2F1%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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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Windsor vacation package cost? ### What are the cheapest months to go to Windsor? ### How many days is enough for Windsor? ### How to find the best Windsor package deals? ### Is it cheaper to book a Windsor vacation as a package? ### When to book a vacation package to Windsor? ### Does Expedia offer Book Now, Pay Later Windsor vacation packages? \* 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 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