Title: Visit Winchester: 2026 Travel Guide for Winchester, Oregon | Expedia.com [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)[Winchester Vacation Packages](https://expedia.com/Winchester.d12104.Destination-Travel-Guides) # Winchester, OR ## Travel Guide ## Visit Winchester - Winchester Hotel Deals - Vacation Rentals in Winchester ![Singing Waters at N. Umpqua](https://images.trvl-media.com/lodging/94000000/93410000/93403100/93403065/65e56f7d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Singing Waters at N. Umpqua Roseburg North OR Stay at this vacation home in Roseburg North. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Winchester Dam and Becker Vineyard are ... 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=4%2F10%2F2026&endDate=4%2F11%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) [](https://expedia.com/Hotel-Search?startDate=4%2F10%2F2026&endDate=4%2F11%2F2026&selected=93403065&PinnedHotelID=93403065&HadPinnedHotel=true®ionId=12104) ![The Lodge at Roseburg](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/54e5b16d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Lodge at Roseburg 375 Harvard Blvd Roseburg OR Fully refundableReserve now, pay when you stay $127 nightly $139 total Apr 3 - Apr 4 Total with taxes and fees Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ... 8.8/10 Excellent! (1,001 reviews) My only complaint was pipes in tub had a bad smell when water ran down from shower and plug was broke off so couldn't close it. Also soap dispenser was stripped from wall making it hard to get soap out. Reviewed on Mar 26, 2026 [](https://expedia.com/Hotel-Search?startDate=4%2F3%2F2026&endDate=4%2F4%2F2026&selected=22705&PinnedHotelID=22705&HadPinnedHotel=true®ionId=12104) ![SureStay by Best Western Roseburg](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/1c101170_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### SureStay by Best Western Roseburg 2855 NW Edenbower Blvd Roseburg OR $95 nightly $104 total Mar 29 - Mar 30 Total with taxes and fees Book a stay at this business-friendly hotel in Roseburg. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ... 8/10 Very Good! (1,000 reviews) The staff was incredibly friendly and accommodating the hotel was also a good price. I didn't like that the breakfast area was closed except during breakfast hours. It's nice to have somewhere to sit and/or eat meals of your own outside of the room. The dining area was also super small, but it sounds ... Reviewed on Mar 24, 2026 [](https://expedia.com/Hotel-Search?startDate=3%2F29%2F2026&endDate=3%2F30%2F2026&selected=539504&PinnedHotelID=539504&HadPinnedHotel=true®ionId=12104) [See all 114 properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience&startDate=3%2F28%2F2026&endDate=3%2F29%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. ![Singing Waters at N. Umpqua](https://images.trvl-media.com/lodging/94000000/93410000/93403100/93403065/65e56f7d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Singing Waters at N. Umpqua Roseburg North OR Stay at this vacation home in Roseburg North. Enjoy a beach locale, laundry facilities, and patios. Popular attractions Winchester Dam and Becker Vineyard are ... 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 [](https://expedia.com/Roseburg-North-Hotels-Singing-Waters-At-N-Umpqua.h93403065.Hotel-Information) ![Bailey River House – Scenic Riverside Retreat on the North Umpqua](https://images.trvl-media.com/lodging/123000000/122930000/122928000/122927960/w1026h679x0y0-4fc4ced3_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bailey River House – Scenic Riverside Retreat on the North Umpqua Roseburg North OR Stay at this vacation home in Roseburg North. Enjoy laundry facilities and air conditioning. Popular attractions Winchester Dam and Becker Vineyard are located ... [](https://expedia.com/Roseburg-North-Hotels-Bailey-River-House-Scenic-Riverside-Retreat-On-The-North-Umpqua.h122927960.Hotel-Information) ![Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital](https://images.trvl-media.com/lodging/71000000/70500000/70497600/70497599/f6e3e2e2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Adorable 2 bedroom 1 bath house pet friendly nearby shopping and hospital Roseburg OR Book a stay at this golf vacation home in Roseburg. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Umpqua Valley Tennis Center and Stewart ... 9.6/10 Exceptional! (54 reviews) Exactly what we needed! Thank you Reviewed on Mar 19, 2026 [](https://expedia.com/Roseburg-Hotels-Adorable-2-Bedroom-1-Bath-House-Pet-Friendly-Nearby-Shopping-And-Hospital.h70497599.Hotel-Information) [See all properties in Winchester](https://expedia.com/Hotel-Search?rfrrid=TG.LP.Hotels.DestinationExperience®ionId=12104&sort=VACATION_RENTAL) 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. ## Check Winchester hotel availability [Tonight ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12104&startDate=2026-03-27&endDate=2026-03-28)[Mar 27 - Mar 28](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12104&startDate=2026-03-27&endDate=2026-03-28) [Tomorrow night ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12104&startDate=2026-03-28&endDate=2026-03-29)[Mar 28 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12104&startDate=2026-03-28&endDate=2026-03-29) [This weekend ](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12104&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026)[Mar 27 - Mar 29](https://expedia.com/Hotel-Search?rfrrid=TG.LP.CheckPrices.DestinationExperience&adults=2&openPlayBack=true®ionId=12104&startDate=3%2F27%2F2026&endDate=3%2F29%2F2026) ## Cities near Winchester ![Roseburg](https://images.trvl-media.com/place/6025867/33540d9e-d8b6-42af-9ea5-60e9649fd915.jpg?impolicy=fcrop&w=512&h=288&q=medium) ### Roseburg ## Explore a world of travel with Expedia - 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[Flights from Colorado Springs (COS) to Roseburg (RBG) ](https://www.expedia.com/lp/flights/cos/rbg/colorado-springs-to-roseburg) - [Flights from Greenville (GSP) to Roseburg (RBG) ](https://www.expedia.com/lp/flights/gsp/rbg/greenville-to-roseburg) - [Flights from Kansas City (MCI) to Roseburg (RBG) ](https://www.expedia.com/lp/flights/mci/rbg/kansas-city-to-roseburg) - [Flights from Montgomery (MGM) to Roseburg (RBG) ](https://www.expedia.com/lp/flights/mgm/rbg/montgomery-to-roseburg) - [Flights from St. Louis (SUS) to Roseburg (RBG) ](https://www.expedia.com/lp/flights/sus/rbg/st-louis-to-roseburg) - [Flights from Montreal (YMX) to Roseburg (RBG) ](https://www.expedia.com/lp/flights/ymx/rbg/montreal-to-roseburg) - [Flights from Gold Beach (GOL) to Roseburg (RBG) ](https://www.expedia.com/lp/flights/gol/rbg/gold-beach-to-roseburg) - [Flights to Roseburg ](https://www.expedia.com/Cheap-Flights-To-Roseburg.d6054633.Travel-Guide-Flights) - [Flights from Roseburg ](https://www.expedia.com/lp/flights/6054633/flights-from-roseburg) - [Winchester Dam ](https://www.expedia.com/Winchester-Dam-Roseburg.d6296129.Vacation-Attraction) - [Visit Roseburg ](https://www.expedia.com/Roseburg.dx6054633) - [Becker Vineyard ](https://www.expedia.com/Becker-Vineyard-Roseburg.d553248621532642248.Vacation-Attraction) - [Glaser Estate Winery & Distillery ](https://www.expedia.com/Glaser-Estate-Winery-Distillery-Roseburg.d553248621532642247.Vacation-Attraction) - [Discovery Garden ](https://www.expedia.com/Discovery-Garden-Roseburg.d553248621532642245.Vacation-Attraction) - [Stewart Park ](https://www.expedia.com/Stewart-Park-Roseburg.d553248621561869686.Vacation-Attraction) - [Car rentals near Wilbur ](https://www.expedia.com/Car-Rentals-In-Wilbur.d553248635975876340.Car-Rental-Guide) - [Car rentals near Roseburg North ](https://www.expedia.com/Car-Rentals-In-Roseburg-North.d553248634983194873.Car-Rental-Guide) - [Car rental Roseburg Airport (RBG) ](https://www.expedia.com/Car-Rentals-In-Roseburg-Regional.d6031434.Car-Rental-Guide) - [Car rentals near Roseburg ](https://www.expedia.com/Car-Rentals-In-Roseburg.d6054633.Car-Rental-Guide) - [Enterprise Rental Cars in Roseburg ](https://www.expedia.com/Enterprise-Car-Rentals-In-Roseburg.d6054633-c15.Car-Rental-Guide-Suppliers) - [Hertz Rental Cars in Roseburg ](https://www.expedia.com/Hertz-Car-Rentals-In-Roseburg.d6054633-c40.Car-Rental-Guide-Suppliers) - [National Car Rental Rental Cars in Roseburg ](https://www.expedia.com/National-Car-Rental-Car-Rentals-In-Roseburg.d6054633-c42.Car-Rental-Guide-Suppliers) - [Budget Rental Cars in Roseburg ](https://www.expedia.com/Budget-Car-Rentals-In-Roseburg.d6054633-c39.Car-Rental-Guide-Suppliers) - [Avis Rental Cars in Roseburg ](https://www.expedia.com/Avis-Car-Rentals-In-Roseburg.d6054633-c41.Car-Rental-Guide-Suppliers) - [Roseburg Vacation Rentals ](https://www.expedia.com/Roseburg-Vacation-Rentals.d6054633.Travel-Guide-VacationRentals) - Cities near Winchester - Places of interest [Roseburg](https://expedia.com/Roseburg.dx6054633) - [Wildlife Safari ](https://expedia.com/Wildlife-Safari-Winston.d6090413.Vacation-Attraction) - [Umpqua National Forest ](https://expedia.com/Umpqua-National-Forest-Oregon.d6090410.Vacation-Attraction) - [North Umpqua River ](https://expedia.com/North-Umpqua-River-Oregon.d681930248940662784.Vacation-Attraction) - [Umpqua River ](https://expedia.com/Umpqua-River-Oregon.d681931512707526656.Vacation-Attraction) - [Melrose Vineyards ](https://expedia.com/Melrose-Vineyards-Roseburg.d6090409.Vacation-Attraction) - [Stewart Park ](https://expedia.com/Stewart-Park-Roseburg.d553248621561869686.Vacation-Attraction) - [South Umpqua River ](https://expedia.com/South-Umpqua-River-Oregon.d684502648556560384.Vacation-Attraction) - [Douglas County Museum of History and Natural History ](https://expedia.com/Douglas-County-Museum-Of-History-And-Natural-History-Roseburg.d553248621532642241.Vacation-Attraction) - [Reustle Prayer Rock Vineyards ](https://expedia.com/Reustle-Prayer-Rock-Vineyards-Roseburg.d553248621532642250.Vacation-Attraction) - [HillCrest Winery and Distillery ](https://expedia.com/HillCrest-Winery-And-Distillery-Roseburg.d6090407.Vacation-Attraction) - [Umpqua Golf Resort ](https://expedia.com/Umpqua-Golf-Resort-Sutherlin.d553248621554455067.Vacation-Attraction) - [Spangler Vineyards ](https://expedia.com/Spangler-Vineyards-Roseburg.d553248621532642240.Vacation-Attraction) - [Winchester Dam ](https://expedia.com/Winchester-Dam-Roseburg.d6296129.Vacation-Attraction) - [Abacela Winery ](https://expedia.com/Abacela-Winery-Winston.d553248621532642236.Vacation-Attraction) - [Girardet Wine Cellars ](https://expedia.com/Girardet-Wine-Cellars-Roseburg.d553248621532642235.Vacation-Attraction) - [Oakland City Park ](https://expedia.com/Oakland-City-Park-Oakland.d553248621554455068.Vacation-Attraction) - [Discovery Garden ](https://expedia.com/Discovery-Garden-Roseburg.d553248621532642245.Vacation-Attraction) - [MarshAnne Landing ](https://expedia.com/MarshAnne-Landing-Oakland.d553248621532642252.Vacation-Attraction) - [Glaser Estate Winery & Distillery ](https://expedia.com/Glaser-Estate-Winery-Distillery-Roseburg.d553248621532642247.Vacation-Attraction) - [Becker Vineyard ](https://expedia.com/Becker-Vineyard-Roseburg.d553248621532642248.Vacation-Attraction) ![](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. 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