Title: Winchester Vacation Packages & Trips 2026 from CA $992 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d177515.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d177515.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.ca/Cheap-Flights-To-Winchester.d177515.Travel-Guide-Flights)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d177515.Car-Rental-Guide) ![](https://images.trvl-media.com/place/177515/c6b76f6b-4f1e-4d6f-ab58-14153246d2cd.jpg?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 The rich history and spectacular views are just the start of the things Winchester has on offer. Experience the very best of this interesting city your way with a tailor-made Winchester vacation package. Any trip to Winchester should include some sightseeing. [Hammers](https://www.expedia.ca/Hammers-Winchester.d553248621532655570.Vacation-Attraction) is a great place to kick things off. Whoever you're going away with and whatever you want to spend, your dream Winchester vacation is just a few clicks away with Expedia. ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![Candlewood Suites Murfreesboro by IHG](https://images.trvl-media.com/lodging/4000000/3570000/3566100/3566068/19849d7d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Candlewood Suites Murfreesboro by IHG CA $992 per person Jun 12 - Jun 19 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Nashville (BNA) 8.4/10 Very Good! (530 reviews) The hotel is good for a travelers Reviewed on Mar 22, 2026 ![Margaritaville Hotel Nashville](https://images.trvl-media.com/lodging/34000000/33800000/33793300/33793279/72640c64_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Margaritaville Hotel Nashville Downtown Nashville CA $2,095 per person Jun 3 - Jun 9 found 1 day ago Roundtrip non-stop flight included Edmonton (YEG) to Nashville (BNA) 9.2/10 Wonderful! (1,935 reviews) Very nice hotel. Easy walk to Broadway. Staff was very pleasant, friendly and accomodating. Rooms were clean, nicely decorated and equipped with everything you need for you stay. Would stay here again. Reviewed on Mar 26, 2026 ![The Harpeth Franklin Downtown, Curio Collection by Hilton](https://images.trvl-media.com/lodging/38000000/37810000/37805100/37805042/fb99c1f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Harpeth Franklin Downtown, Curio Collection by Hilton Historic Downtown Franklin CA $2,318 per person Jun 12 - Jun 19 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Nashville (BNA) 9.6/10 Exceptional! (503 reviews) Excellent property and location Reviewed on Mar 23, 2026 ![Landing Furnished Apartments near Barfield](https://images.trvl-media.com/lodging/124000000/123030000/123025000/123024995/7e72aef9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Landing Furnished Apartments near Barfield CA $1,414 per person Jun 12 - Jun 19 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Nashville (BNA) No reviews ![The Odyssey Apartments – by AvantStay Designer Stay in Midtown](https://images.trvl-media.com/lodging/117000000/116310000/116300600/116300512/b50859ab_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Odyssey Apartments – by AvantStay Designer Stay in Midtown West End CA $1,298 per person Jun 12 - Jun 19 found 19 hours ago Roundtrip non-stop flight included Toronto (YYZ) to Nashville (BNA) No reviews ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Best Western Inn](https://images.trvl-media.com/lodging/1000000/520000/517600/517564/1e35560b_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Best Western Inn 1602 Dinah Shore Boulevard Winchester TN Fully refundableReserve now, pay when you stay CA $152 CA $174 total Apr 9 - Apr 10 includes taxes & fees 8.8/10 Excellent! (684 reviews) Cons - Very dated building, mold around bath grout, many dead bugs on the floor, spider webs in ceiling corners, the area did not feel safe. Pros- The beds seemed nice and clean and were comfy, it was quiet. Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=09%2F04%2F2026&endDate=10%2F04%2F2026&selected=517564&PinnedHotelID=517564&HadPinnedHotel=true®ionId=177515) ![Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak](https://images.trvl-media.com/lodging/107000000/106530000/106528100/106528058/bb756990_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Whispering Waters-Dock,Slip,Game Room, SUPs/Kayak Winchester TN 10/10 Exceptional! (22 reviews) 10/10\. Whispering Waters was phenomenal. We had 10 girls stay for a long weekend. The weather was great and enjoyed the deck with the lake views. Neighborhood was quiet and peaceful. The living room sat 10 comfy. The kitchen was large and open. Having 2 full stoves was great. Dining room table sat ... Reviewed on Mar 8, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=106528058&PinnedHotelID=106528058&HadPinnedHotel=true®ionId=177515) [](https://expedia.ca/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=106528058&PinnedHotelID=106528058&HadPinnedHotel=true®ionId=177515) ![Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK](https://images.trvl-media.com/lodging/82000000/81750000/81748200/81748162/9c6efda0_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Lakefront-Lakeview-Steps to the Water-Tim's Ford Lake LUXURY Home & DOCK Winchester TN 10/10 Exceptional! (28 reviews) We had a ladies “Reading Retreat” and had a great time! We loved the house and our group wants to come back again. Everything was thought about from having a lighter for the grill/fire-pit to fresh flowers upon arrival. The ladies even told their husbands and now a guys trip is being planned for ... Reviewed on Mar 6, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=81748162&PinnedHotelID=81748162&HadPinnedHotel=true®ionId=177515) [](https://expedia.ca/Hotel-Search?startDate=10%2F04%2F2026&endDate=11%2F04%2F2026&selected=81748162&PinnedHotelID=81748162&HadPinnedHotel=true®ionId=177515) [See all 713 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=28%2F03%2F2026&endDate=29%2F03%2F2026®ionId=177515) 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) ### Discover the most popular places to visit in Winchester ![Aerial drone view of a lake marina with boats storage on Tims Ford lake in Winchester Tennessee](https://images.trvl-media.com/place/553248621532655563/2002f588-7d16-4565-9128-6ff77f555ed5.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Tim's Ford Marina Bring the kids to Tim's Ford Marina and enjoy the excitement of this amusement park in Winchester. Discover the countryside while you're in the area. [](https://expedia.ca/Tims-Ford-Marina-Winchester.d553248621532655563.Vacation-Attraction) ## 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