Title: Winchester Vacation Packages & Trips 2026 from CA $1,508 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d12104.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d12104.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d12104.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 When a city adventure is calling your name, answer it with a Winchester vacation package. With all your travel plans worked out before you leave, all you have to do here is focus on having fun. Any trip to Winchester needs a well-designed itinerary. Fill yours with big-name attractions like [Melrose Vineyards](https://www.expedia.ca/Melrose-Vineyards-Roseburg.d6090409.Vacation-Attraction), [Stewart Park](https://www.expedia.ca/Stewart-Park-Roseburg.d553248621561869686.Vacation-Attraction) and [Winchester Dam](https://www.expedia.ca/Winchester-Dam-Roseburg.d6296129.Vacation-Attraction). Stop daydreaming and start doing. Browse the wide range of options on Expedia today and put your Winchester vacation plans in motion! ## Top Winchester Vacation Deals Price found within the past 48 hours. Click for updated prices. ![University Inn & Suites](https://images.trvl-media.com/lodging/2000000/1070000/1068100/1068093/26995bbd_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### University Inn & Suites East University CA $1,508 per person Mar 14 - Mar 21 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Eugene (EUG) 8/10 Very Good! (1,488 reviews) Very clean room & comfortable bed. Our room was at the far end & street noise was negligible mid-week. --The refrigerator motor tends to turn on frequently & noticeable during the night, so the next night we turned the temperature down. Reviewed on Feb 7, 2026 ![Valley River Inn](https://images.trvl-media.com/lodging/1000000/10000/2600/2542/cdab6333_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Valley River Inn CA $1,589 per person Mar 14 - Mar 21 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Eugene (EUG) 9.4/10 Exceptional! (1,101 reviews) Nice lobby and Christmas decorations were much appreciated Reviewed on Feb 5, 2026 ![Campbell House Inn](https://images.trvl-media.com/lodging/1000000/900000/899800/899720/41cbc3b7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Campbell House Inn Downtown Eugene CA $1,881 per person Mar 14 - Mar 21 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Eugene (EUG) 9.6/10 Exceptional! (1,001 reviews) Everything was great. Reviewed on Feb 7, 2026 ![The 505 Eugene](https://images.trvl-media.com/lodging/96000000/95270000/95269100/95269076/6a689631_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The 505 Eugene Downtown Eugene CA $1,850 per person Mar 14 - Mar 21 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Eugene (EUG) 9.4/10 Exceptional! (42 reviews) 10/10! This place was clean and easy to find with the provided instructions. Parking was a little tough as the alleyway wasn’t very visible (we came in at 11:30pm) however once we found the painted numbers in the lot we were great! Walkable, convenient and a decent space for what we needed. If you are a light sleeper, this is near the train and it does run frequently. Reviewed on Jul 30, 2025 ![Downtown Inn](https://images.trvl-media.com/lodging/2000000/1350000/1343800/1343778/4d68e14e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Downtown Inn Downtown Eugene CA $1,730 per person Mar 14 - Mar 21 found 3 hours ago Roundtrip non-stop flight included Toronto (YTO) to Eugene (EUG) 9/10 Wonderful! (826 reviews) This place had everything we needed for our one night stay. It was clean and felt safe enough. We were able to walk to the Hult center and find plenty of options to eat dinner nearby. Reviewed on Jan 5, 2026 ## Ready to book your vacation to Winchester? Choose your dates ## Winchester Hotel Deals ![Singing Waters at N. Umpqua](https://images.trvl-media.com/lodging/94000000/93410000/93403100/93403065/ab4dd7f2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Singing Waters at N. Umpqua Roseburg North OR 10/10 Exceptional! (9 reviews) The pictures are exactly how you will find this home. The remodel is first class, the river view amazing. A native of Roseburg, our family stayed here while visiting family. Very peaceful..hosts were very responsive. Reviewed on Sep 12, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) ![SureStay by Best Western Roseburg](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/abf320fc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay by Best Western Roseburg 2855 NW Edenbower Blvd Roseburg OR Fully refundableReserve now, pay when you stay CA $114 CA $125 total Feb 15 - Feb 16 includes taxes & fees 8/10 Very Good! (1,002 reviews) Clean and staff is always nice. Reviewed on Jan 30, 2026 [](https://expedia.ca/Hotel-Search?startDate=15%2F02%2F2026&endDate=16%2F02%2F2026&selected=539504&PinnedHotelID=539504&HadPinnedHotel=true®ionId=12104) ![Riverfront Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Riverfront Inn Roseburg 315 W Harvard Ave Roseburg OR Fully refundableReserve now, pay when you stay 8.4/10 Very Good! (1,427 reviews) The staff were absolutely lovely, and the room was super clean. The only challenge for us was the bed was very hard which some people prefer otherwise a good stay. Reviewed on Jan 26, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=16066&PinnedHotelID=16066&HadPinnedHotel=true®ionId=12104) [](https://expedia.ca/Hotel-Search?startDate=22%2F02%2F2026&endDate=23%2F02%2F2026&selected=16066&PinnedHotelID=16066&HadPinnedHotel=true®ionId=12104) [See all 114 properties in Winchester](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026®ionId=12104) 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