Title: Windsor Vacation Packages 2026 from $408 | 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 $408 ## 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. ![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 $408 per person May 4 - May 8 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.4/10 Very Good! (1,442 reviews) The valet parking was the best! Reviewed on Feb 25, 2026 ![The Washington Boutique Hotel](https://images.trvl-media.com/lodging/100000000/99990000/99982700/99982661/a65e2629_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Washington Boutique Hotel $567 per person Apr 20 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 9/10 Wonderful! (80 reviews) Cute house, neat location. Avoid the crazy neighbor. Reviewed on Oct 19, 2025 ![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 $583 per person May 15 - May 17 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 ![Great Wolf Lodge Sandusky OH](https://images.trvl-media.com/lodging/2000000/1190000/1183600/1183594/371038d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Great Wolf Lodge Sandusky OH $561 per person Apr 20 - Apr 24 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.4/10 Very Good! (1,003 reviews) Always a great experience here. Reviewed on Jan 25, 2026 ![Holiday Inn Cleveland Clinic by IHG](https://images.trvl-media.com/lodging/13000000/12410000/12403300/12403291/08cfbfed_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Holiday Inn Cleveland Clinic by IHG Fairfax $476 per person May 15 - May 17 found 1 day ago Roundtrip flight included Boston (BOS) to Cleveland (CLE) 8.8/10 Excellent! (1,231 reviews) All was good. Fine place to stay while at the Cleveland Clinic. Reviewed on Feb 23, 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/2026-03-25/2026-04-01/?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! (1,003 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 $123 nightly $140 total Feb 26 - Feb 27 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=2%2F26%2F2026&endDate=2%2F27%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 1 - Mar 2 Total with taxes and fees 7.4/10 Good! (1,001 reviews) Staff were friendly, housekeeping was outstanding. Water is hot for a shower, the best. Bed was comfortable, lots of pillows a plus!! It was a nice place to stay and I plan on staying there again. Reviewed on Feb 21, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%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%2F26%2F2026&endDate=2%2F27%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.