Title: Winchester Vacation Packages 2026 from $730 | Expedia.com [Winchester Travel Guide](https://expedia.com/Winchester.dx12104)[Hotels in Winchester](https://expedia.com/Winchester-Hotels.d12104.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.com/Winchester-Vacation-Rentals.d12104.Travel-Guide-VacationRentals)[Flights to Winchester](https://expedia.com/Cheap-Flights-To-Winchester.d12104.Travel-Guide-Flights)[Car Rentals in Winchester](https://expedia.com/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 Vacations from $730 ## Book a Hotel + Flight or Car together to unlock savings - ## Plan, book, travel with confidence - ### Better together Save up to $1,045 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.com/Melrose-Vineyards-Roseburg.d6090409.Vacation-Attraction), [Stewart Park](https://www.expedia.com/Stewart-Park-Roseburg.d553248621561869686.Vacation-Attraction) and [Winchester Dam](https://www.expedia.com/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! ## The Latest Winchester vacation packages Price found within the past 48 hours. Click for updated prices. ![Hayward Inn](https://images.trvl-media.com/lodging/1000000/30000/22900/22868/124468bb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Hayward Inn East University $730 per person May 11 - May 17 found 24 hours ago Roundtrip non-stop flight included Houston (IAH) to Eugene (EUG) 8.8/10 Excellent! (2,886 reviews) Good location. The breakfast was average Reviewed on Feb 25, 2026 ![Counting Z's](https://images.trvl-media.com/lodging/103000000/102460000/102451100/102451055/7d9728a2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Counting Z's Save 100% on your flight $5,712 per person May 11 - May 17 found 24 hours ago Roundtrip non-stop flight included Houston (IAH) to Eugene (EUG) 7.8/10 Good! (163 reviews) Room was totally cute clean the staff is wonderful . Cool little house great idea making it a little hotel. Thanks guys we enjoyed ourselves. Reviewed on Feb 22, 2026 ![The Gordon Hotel](https://images.trvl-media.com/lodging/56000000/55540000/55532400/55532324/f64450d7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Gordon Hotel Downtown Eugene $1,171 per person May 11 - May 17 found 24 hours ago Roundtrip non-stop flight included Houston (IAH) to Eugene (EUG) 9.6/10 Exceptional! (1,000 reviews) I loved the speak easy, it was a nice diversion! Reviewed on Feb 19, 2026 ![Signature Inn Eugene](https://images.trvl-media.com/lodging/3000000/2170000/2163100/2163040/35896c5e_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Signature Inn Eugene West Eugene $1,432 per person May 11 - May 17 found 24 hours ago Roundtrip non-stop flight included Houston (IAH) to Eugene (EUG) 8/10 Very Good! (524 reviews) This has become my go-to place to stay. The gentleman that runs it is very nice and the rooms are exceptionally clean. And he keeps tootsie rolls in the lobby. 😋 Reviewed on Jan 30, 2026 ![Courtyard by Marriott Corvallis](https://images.trvl-media.com/lodging/20000000/19530000/19520500/19520442/ad71731b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Courtyard by Marriott Corvallis Downtown Corvallis $1,240 per person May 11 - May 17 found 24 hours ago Roundtrip non-stop flight included Houston (IAH) to Eugene (EUG) 9.4/10 Exceptional! (689 reviews) Clean room and convenient location. Reviewed on Dec 24, 2025 Don't see what you're looking for? See all available trips from Columbus to Winchester [View all trips](https://expedia.com/go/package/search/FlightHotel/2026-03-26/2026-04-02/?FromAirport=Columbus,%20Ohio,%20United%20States%20of%20America&Destination=EUG&NumRoom=1&NumAdult=2&NumChild=0&paandie=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.com/deals?rfrr=PKG_SPRING_PROMO_12104) ## 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.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) [](https://expedia.com/Hotel-Search?startDate=3%2F12%2F2026&endDate=3%2F13%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) ![Holiday Inn Express Roseburg by IHG](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/a366b61d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Holiday Inn Express Roseburg by IHG 375 Harvard Blvd Roseburg OR Fully refundableReserve now, pay when you stay $99 nightly $108 total Mar 5 - Mar 6 Total with taxes and fees 8.8/10 Excellent! (1,002 reviews) Convenient location. Clean room. Gorgeous view from balcony. Good breakfast. Reviewed on Feb 25, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F5%2F2026&endDate=3%2F6%2F2026&selected=22705&PinnedHotelID=22705&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 $72 nightly $79 total Mar 1 - Mar 2 Total with taxes and fees 8/10 Very Good! (1,007 reviews) Nice staff, clean room, nice breakfast. Not fancy but perfectly suitable for a quick stay. Reviewed on Feb 23, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F1%2F2026&endDate=3%2F2%2F2026&selected=539504&PinnedHotelID=539504&HadPinnedHotel=true®ionId=12104) [See all 118 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=2%2F27%2F2026&endDate=2%2F28%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. ## Find the Best Winchester Vacation Packages ## Winchester Essential Information | Language | English | | --------------- | ----------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------------- | | Currency | U.S dollars | | Max Temp Winter | 50ºF | | Max Temp Summer | 80ºF | | Top Sights | [Wildlife Safari](https://www.expedia.com/Wildlife-Safari-Winston.d6090413.Vacation-Attraction), [Reustle Prayer Rock Vineyards](https://www.expedia.com/Reustle-Prayer-Rock-Vineyards-Roseburg.d553248621532642250.Vacation-Attraction) and [HillCrest Winery and Distillery](https://www.expedia.com/HillCrest-Winery-And-Distillery-Roseburg.d6090407.Vacation-Attraction) | ## More 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![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/23/waterpark-vacations.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Waterpark Vacations [](https://expedia.com/lp/theme-vacations/waterpark-vacations?rfrr=editorial.Waterpark_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/Caribean_scuba_diving.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Scuba Diving Vacations [](https://expedia.com/lp/theme-vacations/scuba-diving-vacations?rfrr=editorial.Scuba_Diving%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/05/08/aruba_yoga.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Yoga Vacations [](https://expedia.com/lp/theme-vacations/yoga-vacations?rfrr=editorial.Yoga_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2023/04/04/EPS-RBC-SummerBeachVacations-AdobeStock_206356322.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Cheap Vacations [](https://expedia.com/lp/theme-vacations/cheap-vacations?rfrr=editorial.Cheap_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2024/06/26/1175883311.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Solo Vacations [](https://expedia.com/lp/b/vacations/solo-vacations?rfrr=editorial.Solo_Vacations.click) ## Frequently asked questions ### How much does a Winchester vacation package cost? ### What are the cheapest months to go to Winchester? ### How many days is enough for Winchester? ### How to find the best Winchester package deals? ### Is it cheaper to book a Winchester vacation as a package? ### When to book a vacation package to Winchester? ### Does Expedia offer Book Now, Pay Later Winchester vacation packages? \* 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 even more - get up to 20% on select hotels 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