Title: Winchester Vacation Packages & Trips 2026 from CA $933 | 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. ![Wampler House](https://images.trvl-media.com/lodging/33000000/32130000/32129400/32129320/daedae09_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wampler House CA $933 per person Jun 12 - Jun 15 found 3 hours ago Roundtrip non-stop flight included Calgary (YYC) to Indianapolis (IND) 9.8/10 Exceptional! (141 reviews) This was a quaint, comfortable, clean stay about 12-15 minutes from the IU campus. Staff was warm and welcoming. Reviewed on Mar 9, 2026 ![Wingate by Wyndham Indianapolis Airport Plainfield](https://images.trvl-media.com/lodging/1000000/1000000/990100/990067/f89b9b5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Wingate by Wyndham Indianapolis Airport Plainfield CA $1,041 per person May 29 - Jun 3 found 10 hours ago Roundtrip flight included Toronto (YYZ) to Indianapolis (IND) 8.2/10 Very Good! (1,004 reviews) The entire staff was right on point friendly, welcoming, and making sure everything was in place. The rooms were as advertised nice and spacious and the bed comfy and the pillows soft. Our cleaning staff was outstanding always going the extra mile making sure we had everything we needed. The entire hotel was clean and in order and it was extremely crowded the entire time I was there. I will definitely stay there again and recommend to family and friends. . Oh and the breakfast was as good as any. Reviewed on Mar 17, 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 $1,961 per person May 29 - Jun 3 found 10 hours ago Roundtrip flight included Toronto (YYZ) to Indianapolis (IND) 9.8/10 Exceptional! (1,844 reviews) The room was beautiful! It’s a neat hotel. Reviewed on Mar 23, 2026 ![Omni Severin Hotel](https://images.trvl-media.com/lodging/1000000/20000/17700/17640/92d3ed84_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Omni Severin Hotel Downtown Indianapolis CA $1,377 per person May 29 - Jun 3 found 24 hours ago Roundtrip flight included Toronto (YYZ) to Indianapolis (IND) 9.4/10 Exceptional! (865 reviews) Adequate gym, friendly staff. Some construction nearby that was a bit noisy outside our room. Reviewed on Mar 26, 2026 ![Courtyard by Marriott Bloomington](https://images.trvl-media.com/lodging/1000000/50000/42600/42510/81f527c3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Bloomington Downtown Bloomington CA $982 per person Jun 12 - Jun 15 found 3 hours ago Roundtrip non-stop flight included Calgary (YYC) to Indianapolis (IND) 8.6/10 Excellent! (1,003 reviews) Main Entrance was blocked had to used side door. Pool was closed because of construction. Reviewed on Mar 16, 2026 ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![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 $134 CA $150 total Mar 28 - Mar 29 includes taxes & fees 9/10 Wonderful! (252 reviews) It’s was good for the money! Would stay again! Reviewed on Mar 8, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F03%2F2026&endDate=29%2F03%2F2026&selected=1778532&PinnedHotelID=1778532&HadPinnedHotel=true®ionId=6046207) ![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=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=24889054&PinnedHotelID=24889054&HadPinnedHotel=true®ionId=6046207) [](https://expedia.ca/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=24889054&PinnedHotelID=24889054&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 $93 CA $104 total Mar 29 - Mar 30 includes taxes & fees 8.4/10 Very Good! (1,000 reviews) We had a long drive behind us with more to come so stopped for the night. The hotel wasn’t fancy but was immaculate, comfortable, value-priced, and offered a breakfast spread equal to hotels that are 1-2 tiers more expensive. (Ask for cook-to-order eggs of any style!) Staff were friendly and competent. ... Reviewed on Mar 25, 2026 [](https://expedia.ca/Hotel-Search?startDate=29%2F03%2F2026&endDate=30%2F03%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=28%2F03%2F2026&endDate=29%2F03%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