Title: Windsor Vacation Packages 2026 from $441 | 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 $441 ## 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. ![Cedar Stables Inn and Suites](https://images.trvl-media.com/lodging/36000000/35900000/35895300/35895256/892165cb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Cedar Stables Inn and Suites Save 100% on your flight $441 per person May 13 - May 17 found 22 hours ago Roundtrip flight included New York (NYC) to Cleveland (CLE) 8.8/10 Excellent! (497 reviews) The room was so nice and cozy! This was our first time staying here and we will definitely be staying again. The room was clean and they even had the good dove shampoo conditioner and soap! We love eating at the thirsty pony so being able to stay at this hotel just made our experience even better with only having a short walk down the hall to the restaurant. Reviewed on Feb 22, 2026 ![Hotel Indigo Cleveland Downtown by IHG](https://images.trvl-media.com/lodging/1000000/120000/119000/119000/11326ddb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hotel Indigo Cleveland Downtown by IHG Downtown Cleveland Save 100% on your flight $629 per person May 8 - May 11 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.4/10 Very Good! (1,586 reviews) love the arena across the street, rally house for gifts, and Clevelander for food and drinks!! Reviewed on Mar 6, 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 Save 100% on your flight $719 per person May 8 - May 11 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.6/10 Excellent! (2,068 reviews) My stay was short as I had a court meeting in the morning but everything was comfortable Reviewed on Mar 2, 2026 ![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 $553 per person May 8 - May 11 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 9/10 Wonderful! (868 reviews) All good except the mold/mildew in the shower Reviewed on Mar 2, 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 Save 100% on your flight $575 per person May 8 - May 11 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 7.6/10 Good! (1,001 reviews) Love staying here for shows at Rocket Mortgage. Clean rooms, friendly staff and close to the venue. Reviewed on Mar 7, 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/2026-04-07/2026-04-14/?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 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/1000000/660000/660000/659951/6708ea96_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 $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) ![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 $55 nightly $64 total Mar 11 - Mar 12 Total with taxes and fees 7.4/10 Good! (1,004 reviews) Small room Reviewed on Mar 3, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F11%2F2026&endDate=3%2F12%2F2026&selected=13716&PinnedHotelID=13716&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 15 - Mar 16 Total with taxes and fees 9.2/10 Wonderful! (829 reviews) Great place all around. Reviewed on Mar 6, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F15%2F2026&endDate=3%2F16%2F2026&selected=1372060&PinnedHotelID=1372060&HadPinnedHotel=true®ionId=6180248) [See all 562 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F8%2F2026&endDate=3%2F9%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