Title: Windsor Vacation Packages 2026 | Expedia.com [Windsor Travel Guide](https://expedia.com/Windsor.dx175567)[Hotels in Windsor](https://expedia.com/Windsor-Hotels.d175567.Travel-Guide-Hotels)[Vacation Rentals in Windsor](https://expedia.com/Windsor-Vacation-Rentals.d175567.Travel-Guide-VacationRentals)[Flights to Windsor](https://expedia.com/Cheap-Flights-To-Windsor.d175567.Travel-Guide-Flights)[Car Rentals in Windsor](https://expedia.com/Car-Rentals-In-Windsor.d175567.Car-Rental-Guide) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium) # Windsor Vacations ## 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 a getaway to the city is calling your name, answer it with a Windsor vacation package. With all your travel arrangements under control before you go, all you have to do here is focus on having the time of your life. Fill your trip to Windsor with tours of its big-hitting attractions. First stop? Make a beeline for [Wolf Creek State Park](https://www.expedia.com/Wolf-Creek-State-Park-Illinois.d553248621561881810.Vacation-Attraction). Whoever you're traveling with and whatever your bank balance, your ultimate Windsor vacation is just a few clicks away with Expedia. ![](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_175567) ## Windsor Hotel Deals ![Comfort Suites Mattoon East](https://images.trvl-media.com/lodging/1000000/480000/474300/474235/6759fc3e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Comfort Suites Mattoon East 1408 Broadway Ave E Mattoon IL Fully refundableReserve now, pay when you stay $85 nightly $95 total Mar 19 - Mar 20 Total with taxes and fees 8.8/10 Excellent! (911 reviews) Everything was great. Definitely will stay there the next time we are in Mattoon. Reviewed on Feb 27, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F19%2F2026&endDate=3%2F20%2F2026&selected=474235&PinnedHotelID=474235&HadPinnedHotel=true®ionId=175567) ![Super 8 by Wyndham Mattoon](https://images.trvl-media.com/lodging/1000000/50000/49800/49707/2e073a1e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Super 8 by Wyndham Mattoon 205 Mcfall Rd Mattoon IL Fully refundableReserve now, pay when you stay $65 nightly $73 total Mar 12 - Mar 13 Total with taxes and fees 7.4/10 Good! (709 reviews) Door didn't lock from the outside, terrible breakfast, no cleaning on the weekends, but the bed was amazing Reviewed on Feb 18, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=49707&PinnedHotelID=49707&HadPinnedHotel=true®ionId=175567) ![Holiday Inn Express & Suites Mattoon by IHG](https://images.trvl-media.com/lodging/2000000/1860000/1850700/1850633/c6bf8414_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express & Suites Mattoon by IHG 121 Swords Dr Mattoon IL Fully refundable $112 nightly $125 total Mar 16 - Mar 17 Total with taxes and fees 8.2/10 Very Good! (767 reviews) The pillows sucked. Reviewed on Feb 26, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F16%2F2026&endDate=3%2F17%2F2026&selected=1850633&PinnedHotelID=1850633&HadPinnedHotel=true®ionId=175567) [See all 104 properties in Windsor](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=3%2F2%2F2026&endDate=3%2F3%2F2026®ionId=175567) 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 | | Closest Airport | Decatur Airport (DEC) | | Population | 1,150 | | Max Temp Winter | 35ºF | | Max Temp Summer | 80ºF | | Top Sights | [Lake Shelbyville Beach](https://www.expedia.com/Lake-Shelbyville-Beach-Shelbyville.d553248621594973941.Vacation-Attraction), [Wolf Creek State Park](https://www.expedia.com/Wolf-Creek-State-Park-Illinois.d553248621561881810.Vacation-Attraction) and [The Little Theatre on the Square](https://www.expedia.com/The-Little-Theatre-On-The-Square-Sullivan.d553248621532658372.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 [](https://expedia.com/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.com/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Kid Friendly Vacations [](https://expedia.com/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Kid_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.com/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.com/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.com/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.com/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ![Gay Friendly Vacations](https://forever.travel-assets.com/flex/flexmanager/images/2023/06/15/LGBTQIA_Holiday_Package.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) LGBTQ Friendly Vacations [](https://expedia.com/lp/theme-holidays/gay-friendly-holidays?rfrr=editorial.LGBTQ_Friendly%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2017/07/05/170615_Adventure_1320_2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adventure Vacations [](https://expedia.com/lp/theme-vacations/adventure-vacations?rfrr=editorial.Adventure_Vacations.click) ![Vacations in Month](https://forever.travel-assets.com/flex/flexmanager/images/2023/05/10/mesog-34434-card-venice.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Where to go when [](https://expedia.com/lp/b/where-to-go-when?rfrr=editorial.Where_to%20go%20when.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/21/honeymoon_hawaii.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Honeymoon Vacations [](https://expedia.com/lp/theme-vacations/honeymoon-vacations?rfrr=editorial.Honeymoon_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/Mountain-vacations.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Mountain Vacations [](https://expedia.com/lp/theme-vacations/mountain-vacations?rfrr=editorial.Mountain_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/fishing-vacations-2.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Fishing Vacations [](https://expedia.com/lp/theme-vacations/fishing-vacations?rfrr=editorial.Fishing_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2019/05/16/Hyatt%20Zilara%20Cancun%20-%20All%20Inclusive%20-%20Adults%20Only.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Adults Only Vacations [](https://expedia.com/lp/theme-vacations/adults-only-vacations?rfrr=editorial.Adults_Only%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](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