Title: Book the Best Winston WINERY Hotels in 2025 | Expedia.ca [Hotels in Winston](https://expedia.ca/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Vacation Rentals in Winston](https://expedia.ca/Winston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals)[Flights to Winston](https://expedia.ca/Cheap-Flights-To-Winston.d6124402.Travel-Guide-Flights)[Things to do in Winston](https://expedia.ca/Things-To-Do-In-Winston.d6124402.Travel-Guide-Activities)[Winston Car Rentals](https://expedia.ca/Car-Rentals-In-Winston.d6124402.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.ca/Winston.d6124402.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/43f0ab47d1f3578edeadf8a2b3b5b7cb.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michelle Finseth # Find Winery Hotels in Winston, OR from CA $115 ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Winston Winery Hotels Tonight [Oct 14 - Oct 15](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-14&endDate=2025-10-15&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 15 - Oct 16](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-15&endDate=2025-10-16&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-10-24&endDate=2025-10-26&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Winston Winery Hotels ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78310000/78301400/78301309/f90085c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/79000000/78310000/78301400/78301309/49b7d1a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bedrooms, iron/ironing board, travel crib, free WiFi](https://images.trvl-media.com/lodging/79000000/78310000/78301400/78301309/f14d49b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/79000000/78310000/78301400/78301309/56558f73.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Watusi Place - A Modern Umpqua Valley Getaway Winston 10/10 Exceptional (46) "This house is great for a family trip to the Wildlife Safari! The location is perfect and the property is suited to accommodate all ages with plenty of room to spread out. Family games, a place to grill, large kitchen and attention to detail from the cleaning team. " CA $295 CA $627 total includes taxes & fees Nov 11 - Nov 12 [](https://www.expedia.ca/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/6950d5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, blackout drapes, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/94417c21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/f3af2ae0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Inn Roseburg Roseburg 8.6/10 Excellent (1421) "It was a comfortable stay" CA $132 CA $145 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information) ![In-room safe, desk, iron/ironing board, free cribs/infant beds](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/ccce26bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Business centre](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/e0f326ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/64893f99.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/e807ccc6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Roseburg Roseburg 7.8/10 Good (1008) "Was a good stay!" CA $105 CA $115 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/1a3bee3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily on-the-go breakfast](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/c51ee531.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/95d13c97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Roseburg Roseburg 8.2/10 Very good (1012) "The staff was exceptional " CA $136 CA $149 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/32f54617.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/e623a979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/abf320fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/3866516b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Roseburg North Near Medical Center Roseburg 8.0/10 Very good (1006) "We enjoyed our stay " CA $139 CA $152 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/43000000/42980000/42977900/42977823/e6deffb1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/43000000/42980000/42977900/42977823/2239cd3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/43000000/42980000/42977900/42977823/70d1fef9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/43000000/42980000/42977900/42977823/67840d55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Luxury, Full Service Bed and Breakfast - you are the only guest in our home! Roseburg 10/10 Exceptional (23) "My parents stayed here for our son's graduation. They were very impressed with the hosts and warm welcome they received" CA $199 CA $249 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Roseburg-Hotels-Vrbo-Property.h42977823.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630896/5de43753.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, books, music library](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630896/083e57b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630896/216da08d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630896/aa34ed97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Modern Bliss: Chic Retreat w/ Stylish Amenities, Ideal for Vacation & Family Fun Roseburg 9.8/10 Exceptional (34) "This place is great. We have stayed multiple times. Will continue to come back here when in the area. " CA $167 CA $413 total includes taxes & fees Oct 16 - Oct 17 [](https://www.expedia.ca/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/114000000/113520000/113518400/113518339/c59f6e86.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/114000000/113520000/113518400/113518339/47728b62.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace, computer monitors](https://images.trvl-media.com/lodging/114000000/113520000/113518400/113518339/c584097e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![4 bedrooms, desk, iron/ironing board, travel crib](https://images.trvl-media.com/lodging/114000000/113520000/113518400/113518339/a0478c2d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool Roseburg North 9.4/10 Exceptional (13) "great property" CA $303 CA $631 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Roseburg-Hotels-Xenia-Retreat-North-Roseburg-Area-Family-Retreat-With-Seasonal-Pool.h113518339.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/39000000/38320000/38315200/38315160/a698d623.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/39000000/38320000/38315200/38315160/d1ffc9b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/39000000/38320000/38315200/38315160/0bd3e475.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38320000/38315200/38315160/b5e0464b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants Roseburg 10/10 Exceptional (3) "Terry's place was such a treat! The apartment exceeded so many of our expectations and was perfect for our mini vacation. Wonderful features and amenities. Beautiful finishes, linens and furnishings. Super responsive host. We look forward to our next stay!" CA $377 CA $590 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h38315160.Hotel-Information) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/38000000/37920000/37912100/37912072/d29e7b69.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, fireplace](https://images.trvl-media.com/lodging/38000000/37920000/37912100/37912072/900b7532.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/38000000/37920000/37912100/37912072/75dff4ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/38000000/37920000/37912100/37912072/403a2e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historic Downtown Luxurious Apartment Only Steps Away from Local Restaurants Roseburg CA $419 CA $643 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h37912072.Hotel-Information) 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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2025-10-28&endDate=2025-10-29®ionId=6124402&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Hotel Reviews ![Motel 6 Roseburg, OR](//images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/247b3334_y.jpg) ### Motel 6 Roseburg, OR 10/10 Excellent "Great for a quick trip" [](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information) ![Motel 6 Sutherlin, OR](//images.trvl-media.com/lodging/1000000/430000/426000/425916/9d536feb_y.jpg) ### Motel 6 Sutherlin, OR 10/10 Excellent "Very nice Good value " [](https://expedia.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information) ![Riverfront Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043_y.jpg) ### Riverfront Inn Roseburg 10/10 Excellent "Great staff, great area for pets" [](https://expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information) ![Holiday Inn Express Roseburg by IHG](//images.trvl-media.com/lodging/1000000/30000/22800/22705/a366b61d_y.jpg) ### Holiday Inn Express Roseburg by IHG 10/10 Excellent "I had a very good experience staying at this hotel everything was clean comfortable and the staff was great. " [](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information) ![Quality Inn Central Roseburg](//images.trvl-media.com/lodging/1000000/670000/663100/663067/f699f1d4_y.jpg) ### Quality Inn Central Roseburg 10/10 Excellent "Friendly staff." [](https://expedia.ca/Roseburg-Hotels-Quality-Inn-Central-Roseburg.h663067.Hotel-Information) ![Comfort Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "They were great people " [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Best Western Garden Villa Inn](//images.trvl-media.com/lodging/1000000/10000/7100/7049/eff8e6cb_y.jpg) ### Best Western Garden Villa Inn 10/10 Excellent "The room was clean and comfortable. Good value " [](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information) ![Super 8 by Wyndham Roseburg](//images.trvl-media.com/lodging/1000000/160000/159100/159048/ccce26bb_y.jpg) ### Super 8 by Wyndham Roseburg 10/10 Excellent "Nice staff" [](https://expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Safari Inn](//images.trvl-media.com/lodging/9000000/8780000/8777200/8777128/416cc059_y.jpg) ### Safari Inn 10/10 Excellent "The staff us very friendly everytime i come here and the rooms are comfortable" [](https://expedia.ca/Roseburg-Hotels-Safari-Inn.h8777128.Hotel-Information) ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [3 Star Hotels in Glendale](https://www.expedia.ca/3Star-Glendale-Hotels.s30-0-d553248634983148396.Travel-Guide-Filter-Hotels) - [Apartments in Azalea](https://www.expedia.ca/Azalea-Apartments.d553248635975869439-aaApartments.Travel-Guide-Accommodation) - 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