Title: Winchester Vacation Packages & Trips 2025/2026 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d6046207.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d6046207.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d6046207.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 #### Your Winchester Vacation History, cuisine, art and more … There's so much to experience with a Winchester vacation package. And with the ability to customize your city getaway, you know it'll be one that's tough to forget. Want to explore? [Winchester Speedway](https://www.expedia.ca/Winchester-Speedway-Winchester.d6289044.Vacation-Attraction), [Winchester Golf Club](https://www.expedia.ca/Winchester-Golf-Club-Winchester.d553248621582419855.Vacation-Attraction) and [Historic Shopping & Dining District of Winchester, Indiana](https://www.expedia.ca/Historic-Shopping-Dining-District-Of-Winchester-Winchester.d553248621532658844.Vacation-Attraction) are among the leading places to visit during your trip to Winchester. Expedia has what you need to escape your routine. Tailor your vacation to Winchester to suit your style of travel, whatever that may look like. ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA](https://images.trvl-media.com/lodging/25000000/24890000/24889100/24889054/8cd8baa4_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Huge Indiana Family Reunion Villa with Indoor Pool, Hot Tub, Game Rm 8 BR, 7 BA Winchester 9.6/10 Exceptional! (181 reviews) Very nice, large, and clean. Plenty of space for everyone! Only downfall house is very musty especially the basement and chlorine smell from the pool. Cost was a bit high for 10 adults and 2 children for 2 nights was almost 5000 but in then end it was worth it. Hosts are very lovely and great communication. ... Reviewed on Sep 29, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=08%2F11%2F2025&endDate=09%2F11%2F2025&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) [](https://expedia.ca/Hotel-Search?startDate=08%2F11%2F2025&endDate=09%2F11%2F2025&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) ![Randolph Inn and Suites](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/77a3466c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Randolph Inn and Suites 890 E Washington, Winchester, IN Fully refundableReserve now, pay when you stay CA $136 CA $152 total Oct 26 - Oct 27 includes taxes & fees 8.8/10 Excellent! (238 reviews) It was clean. The staff was awesome. I will stay again. Reviewed on Oct 13, 2025 [](https://expedia.ca/Hotel-Search?startDate=26%2F10%2F2025&endDate=27%2F10%2F2025&selected=1778532&PinnedHotelID=1778532&HadPinnedHotel=true®ionId=6046207) ![Days Inn by Wyndham Muncie -Ball State University](https://images.trvl-media.com/lodging/1000000/10000/4600/4571/edaea515_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Days Inn by Wyndham Muncie -Ball State University 3509 N Everbrook Ln, Muncie, IN Fully refundableReserve now, pay when you stay CA $88 CA $99 total Oct 31 - Nov 1 includes taxes & fees 6.6/10 (877 reviews) Room was clean and cool. Parking seemed safe and secure. Only issue I had was check in time. I arrived at 2 after a six hour drive. No rooms were available until the designated time of 3 which I found had to imagine. Reviewed on Oct 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=31%2F10%2F2025&endDate=01%2F11%2F2025&selected=4571&PinnedHotelID=4571&HadPinnedHotel=true®ionId=6046207) [See all 114 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=26%2F10%2F2025&endDate=27%2F10%2F2025®ionId=6046207) 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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)