Title: Winchester Vacation Packages & Trips 2025/2026 from CA $818 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000435714.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) # Winchester Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 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 ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![ White House at Grand Central](https://images.trvl-media.com/lodging/84000000/83130000/83121100/83121050/b3c8bf38_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### White House at Grand Central Grand Center CA $818 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to St. Louis (STL) 8.4/10 Very Good! (121 reviews) It was very easy to access public transportation from this property. The room was very clean, bed was comfortable, and when the hot water got up there it was plentiful and hot. There were a/c and heat available; I used both and each worked fine. My apartment was on third floor, and was accessible only via stairs. It was not a problem for me (it was a workout!), but might be for more physically-impaired folks. Reviewed on Oct 23, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-30/?FromAirport=YEG&Destination=STL&NumRoom=1&NumAdult=2&NumChild=0&hotelId=83121050&paandie=true&dealMarker=WwLsTvnj862AfytbQPlsLHN-DycmGx2Cdht7IC6pRvT---M1A6v4l7F5cG-8PzeK) ![The Knight Center at Washington University](https://images.trvl-media.com/lodging/39000000/38720000/38711900/38711810/302445f4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Knight Center at Washington University CA $1,112 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to St. Louis (STL) 9.4/10 Exceptional! (416 reviews) Great location and the room was perfect Reviewed on Nov 2, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-30/?FromAirport=YEG&Destination=STL&NumRoom=1&NumAdult=2&NumChild=0&hotelId=38711810&paandie=true&dealMarker=sFdKb1rWC74hhEsq90uluKRjtgGzHFjLs-ptgfU4_TvMQjhDd2FRUL-TL50N842F) ![Hampton Inn By Hilton St Louis Airport](https://images.trvl-media.com/lodging/111000000/110650000/110648500/110648496/acc96ed2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hampton Inn By Hilton St Louis Airport Woodson Terrace CA $1,001 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to St. Louis (STL) 8.8/10 Excellent! (81 reviews) Overall, this was the best stay I've had in St. Louis in a very long time the staff were nice. Hotel was very clean, bed super comfortable. And great breakfast option for people that don't eat pork. Reviewed on Oct 26, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-30/?FromAirport=YEG&Destination=STL&NumRoom=1&NumAdult=2&NumChild=0&hotelId=110648496&paandie=true&dealMarker=sFdKb1rWC74hhEsq90uluKRjtgGzHFjLs-ptgfU4_TvmDSp_km_yGFqzBgh6edXk) ![Angad Arts Hotel St. Louis, Tapestry Collection by Hilton](https://images.trvl-media.com/lodging/28000000/27620000/27617000/27616925/25bc97a8_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Angad Arts Hotel St. Louis, Tapestry Collection by Hilton Grand Center CA $1,020 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to St. Louis (STL) 8.8/10 Excellent! (1,013 reviews) Very unique and clean, and friendly staff Reviewed on Nov 3, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-30/?FromAirport=YEG&Destination=STL&NumRoom=1&NumAdult=2&NumChild=0&hotelId=27616925&paandie=true&dealMarker=sFdKb1rWC74hhEsq90uluKRjtgGzHFjLs-ptgfU4_TvWzKqcO46-uPDCt07kfnu0) ![The West End](https://images.trvl-media.com/lodging/107000000/106720000/106715700/106715696/ccf67b25_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The West End Central West End CA $898 per person Jan 23 - Jan 30 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to St. Louis (STL) 8.4/10 Very Good! (349 reviews) We had an amazing time visiting “The Lou” Very nice & clean room! Reviewed on Oct 30, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-23/2026-01-30/?FromAirport=YEG&Destination=STL&NumRoom=1&NumAdult=2&NumChild=0&hotelId=106715696&paandie=true&dealMarker=sFdKb1rWC74hhEsq90uluHfjSn3xU2nbWPde7oJ40XfK5YSkNAxDmhxgz1qRKShn) ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Sleep Inn & Suites](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Sleep Inn & Suites 2401 Holliday Ln, Jacksonville, IL Fully refundable CA $112 CA $125 total Nov 16 - Nov 17 includes taxes & fees 9.2/10 Wonderful! (608 reviews) Quite and very pleasing staff. Reviewed on Nov 3, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=23831866&PinnedHotelID=23831866&HadPinnedHotel=true®ionId=3000435714) ![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Jacksonville Inn 1709 W Morton Ave, Jacksonville, IL Fully refundableReserve now, pay when you stay CA $105 CA $120 total Nov 11 - Nov 12 includes taxes & fees 8.4/10 Very Good! (733 reviews) I booked my room in advance,however I couldn't get in until 3pm! When check-out time is 11am! I didn't like that at all. Reviewed on Nov 2, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F11%2F2025&endDate=12%2F11%2F2025&selected=124218&PinnedHotelID=124218&HadPinnedHotel=true®ionId=3000435714) ![Super 8 by Wyndham Jacksonville](https://images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Super 8 by Wyndham Jacksonville 1003 W Morton Ave, Jacksonville, IL Fully refundableReserve now, pay when you stay CA $80 CA $91 total Nov 16 - Nov 17 includes taxes & fees 8.2/10 Very Good! (609 reviews) Good service Reviewed on Oct 19, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F11%2F2025&endDate=17%2F11%2F2025&selected=123170&PinnedHotelID=123170&HadPinnedHotel=true®ionId=3000435714) [See all 42 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=05%2F11%2F2025&endDate=06%2F11%2F2025®ionId=3000435714) 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. ![](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.ca/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.ca/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) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.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.ca/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.ca/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.ca/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.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* 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 on select hotels and earn double points 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 ![QR code to download the app](data:image/png;base64,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)