Title: Winchester Vacation Packages & Trips 2026 from CA $769 | 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. ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Royal Inn](https://images.trvl-media.com/lodging/1000000/20000/19400/19361/fbb4df49_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Royal Inn CA $769 per person May 7 - May 10 found 4 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Indianapolis (IND) 5.6/10 (310 reviews) Off of 38th street. Not a bad stay just a lot going on around the property Reviewed on Aug 16, 2025 ![Embassy Suites by Hilton Plainfield Indianapolis Airport](https://images.trvl-media.com/lodging/30000000/29150000/29144000/29143999/aaf0f491_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Embassy Suites by Hilton Plainfield Indianapolis Airport CA $1,239 per person May 7 - May 10 found 4 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Indianapolis (IND) 9.4/10 Exceptional! (744 reviews) Everything was great. Room was clean and comfortable. The upper windows were dirty but only my husband would put the shades up that high. Breakfast was good but the eggs were cold both mornings. Really enjoyed our stay Reviewed on Mar 21, 2026 ![WoodSpring Suites Indianapolis Castleton](https://images.trvl-media.com/lodging/45000000/44210000/44205000/44204906/25a4e4f1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### WoodSpring Suites Indianapolis Castleton Castleton CA $797 per person May 6 - May 11 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Indianapolis (IND) 7.4/10 Good! (453 reviews) Proximity to stores, restaurants and other public amenities Reviewed on Feb 17, 2026 ![Courtyard by Marriott Indianapolis Plainfield](https://images.trvl-media.com/lodging/60000000/59650000/59648800/59648794/2ad412cc_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Indianapolis Plainfield CA $1,275 per person May 7 - May 10 found 4 hours ago Roundtrip non-stop flight included Winnipeg (YWG) to Indianapolis (IND) 9.2/10 Wonderful! (287 reviews) Clean room and hotel overall. Courteous service from staff Reviewed on Jan 27, 2026 ![Bottleworks Hotel](https://images.trvl-media.com/lodging/58000000/57260000/57258100/57258038/78e86d9a_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Bottleworks Hotel Downtown Indianapolis CA $1,181 per person May 29 - May 31 found 1 day ago Roundtrip non-stop flight included Vancouver (YVR) to Indianapolis (IND) 9.8/10 Exceptional! (1,844 reviews) Awesome boutique hotel. Close to shopping, amazing food,wonderful spa. Reviewed on Mar 30, 2026 ## 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/f29bf352_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 IN 9.8/10 Exceptional! (200 reviews) We have rented large reunion places before. This one looks better online than it was in person. Functionally everything worked, but the decor and furniture were highly dated, hence four stars instead of five. The cleanliness was OK except in the basement, which was very dusty. We had great conversations ... Reviewed on Mar 8, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) [](https://expedia.ca/Hotel-Search?startDate=16%2F04%2F2026&endDate=17%2F04%2F2026&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) ![Randolph Inn and Suites](https://images.trvl-media.com/lodging/2000000/1780000/1778600/1778532/c5613c1c_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 $135 CA $151 total May 1 - May 2 includes taxes & fees 9/10 Wonderful! (253 reviews) There are 2 properties, a motel and a hotel. This is NOT clear when you are making a reservation thru Expedia. The motel is older. The beds are super low. The shower is small. You have to drive to the hotel to eat breakfast and check in/out. The breakfast was good with hot items. The pool was closed ... Reviewed on Mar 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=01%2F05%2F2026&endDate=02%2F05%2F2026&selected=1778532&PinnedHotelID=1778532&HadPinnedHotel=true®ionId=6046207) ![Baymont by Wyndham Richmond I-70](https://images.trvl-media.com/lodging/1000000/10000/4400/4345/97f2f944_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Baymont by Wyndham Richmond I-70 912 Mendleson Dr Richmond IN Fully refundableReserve now, pay when you stay CA $96 CA $107 total Apr 5 - Apr 6 includes taxes & fees 8.4/10 Very Good! (1,005 reviews) Looking from the outside, I was not impressed but my room was clean, the air conditioner kept the room cool and the breakfast was excellent, especially for the price I paid. I would definitely stay here again. Reviewed on Mar 31, 2026 [](https://expedia.ca/Hotel-Search?startDate=05%2F04%2F2026&endDate=06%2F04%2F2026&selected=4345&PinnedHotelID=4345&HadPinnedHotel=true®ionId=6046207) [See all 136 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=03%2F04%2F2026&endDate=04%2F04%2F2026®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