Title: Book the Best Winston WINERY Hotels in 2026 | 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) ![The Wildlife Safari is such an awesome place! It has been around for 38 years and was one of my favorite places I ever visited as a child. My children feel the same after visiting in the summer of 2014. This 600 acre park is home to over 500 animals and features a drive through park as well as a walk through viewing area, cafe and gift shop. One of our favorite parts is in a particular area of the drive-thru park, you can buy food and feed the animals which are emus and different types of deer from your car. Get your camera ready as hilarity ensues! http://www.wildlifesafari.net](https://images.trvl-media.com/place/6090413/6a7f406c-e7ef-4707-844b-63d5d9268f55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michelle Finseth # Find Winery Hotels in Winston, OR from CA $100 - ![](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 [Dec 9 - Dec 10](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-12-09&endDate=2025-12-10&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 10 - Dec 11](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-12-10&endDate=2025-12-11&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-12-12&endDate=2025-12-14&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2025-12-19&endDate=2025-12-21&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winston hotels with winery ![Outdoor dining](https://images.trvl-media.com/lodging/79000000/78310000/78301400/78301309/f90085c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78310000/78301400/78301309/c22e265c.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) ### The Watusi Place - A Modern Umpqua Valley Getaway Winston 10/10 Exceptional (47) "The house was amazing! Easy to get in, clean and well stocked. Definitely recommend to anyone looking for a nice place." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amy H. CA $205 CA $504 total includes taxes & fees Dec 18 - Dec 19 [](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) ![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) ![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) ### Riverfront Inn Roseburg Roseburg 8.6/10 Excellent (1420) "Check in was super easy and the room was clean and comfortable. " ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Melanie [](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) ![Property amenity](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/e807ccc6.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) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/0c6d6cb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Roseburg Roseburg 7.8/10 Good (1005) "The room was clean the beds were very comfortable and the staff was very nice♥️ I would stay here again!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) varyl CA $92 CA $100 total includes taxes & fees Dec 15 - Dec 16 [](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/1000000/20000/17800/17750/2c756f0f.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) ![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 (1005) "The room was very clean and the staff were great." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robbin CA $111 CA $121 total includes taxes & fees Dec 21 - Dec 22 [](https://www.expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Standard Room, 2 Double Beds, Accessible, Non Smoking (Pet Friendly)](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/0ce9df79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/393ea3cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor pool](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/71e42792.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Birthday party area](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/67012fa5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SureStay by Best Western Roseburg Roseburg 8.0/10 Very good (1001) "Very friendly desk staff, room is nice, clean and comfortable. Haven driven past on the freeway will be staying again in the future " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ray CA $109 CA $120 total includes taxes & fees Dec 21 - Dec 22 [](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) ![Dining](https://images.trvl-media.com/lodging/43000000/42980000/42977900/42977823/67840d55.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) ![Interior](https://images.trvl-media.com/lodging/43000000/42980000/42977900/42977823/2239cd3b.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 (24) "My parents stayed here for our son's graduation. They were very impressed with the hosts and warm welcome they received" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SharonLee S. CA $268 CA $336 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Roseburg-Hotels-Vrbo-Property.h42977823.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) ![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) ![Interior](https://images.trvl-media.com/lodging/39000000/38320000/38315200/38315160/4e4d35d6.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) ### 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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CARISSA F. CA $275 CA $460 total includes taxes & fees Dec 13 - Dec 14 [](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/84000000/83640000/83630900/83630896/5de43753.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630896/11d76b83.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 (37) "Just as advertised! Great house. Would definitely stay there again." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jake G. CA $149 CA $389 total includes taxes & fees Dec 14 - Dec 15 [](https://www.expedia.ca/Roseburg-Hotels-Modern-Westside-3BR-Bungalow-W-Private-Backyard.h83630896.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/107000000/106920000/106918700/106918670/9e164ac5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/107000000/106920000/106918700/106918670/ddb8344d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, bed sheets](https://images.trvl-media.com/lodging/107000000/106920000/106918700/106918670/c1a1fb93.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106920000/106918700/106918670/a25e8e91.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### the Bunkhouse coyote- Private Studio Retreat Room Winston 10/10 Exceptional (1) "The views are out of this world! The horses on property are gorgeous! This truly felt like a vacation within a vacation (drove that way for the wildlife safari park). We plan to come back again! Property owner is a sweetheart! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Charles B. CA $106 CA $163 total includes taxes & fees Dec 10 - Dec 11 [](https://www.expedia.ca/Roseburg-Hotels-The-Bunkhouse-Coyote-Private-Studio-Retreat-Room.h106918670.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) ![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) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113520000/113518400/113518339/ab1adb13.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) ### Xenia Retreat- North Roseburg Area Family Retreat with Seasonal Pool Roseburg North 9.4/10 Exceptional (18) "This property was very enjoyable for the children and I enjoyed the kitchen." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stacy B. CA $298 CA $618 total includes taxes & fees Dec 18 - Dec 19 [](https://www.expedia.ca/Roseburg-Hotels-Xenia-Retreat-North-Roseburg-Area-Family-Retreat-With-Seasonal-Pool.h113518339.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=2025-12-23&endDate=2025-12-24®ionId=6124402&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Winston Hotel Reviews ![Super 8 by Wyndham Roseburg](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/ccce26bb_y.jpg) ### Super 8 by Wyndham Roseburg 10/10 Excellent "The room was clean the beds were very comfortable and the staff was very nice♥️ I would stay here again!!" [](https://expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Holiday Inn Express Roseburg by IHG](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/a366b61d_y.jpg) ### Holiday Inn Express Roseburg by IHG 10/10 Excellent "Room was very nice " [](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information) ![Best Western Garden Villa Inn](https://images.trvl-media.com/lodging/1000000/10000/7100/7049/eff8e6cb_y.jpg) ### Best Western Garden Villa Inn 10/10 Excellent "Staff was awesome!" [](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information) ![Riverfront Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043_y.jpg) ### Riverfront Inn Roseburg 10/10 Excellent "I’ve stayed here plenty of times and I have never been disappointed. Always friendly and welcoming. Clean rooms and a great staff " [](https://expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information) ![SureStay by Best Western Roseburg](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/abf320fc_y.jpg) ### SureStay by Best Western Roseburg 10/10 Excellent "Very friendly desk staff, room is nice, clean and comfortable. Haven driven past on the freeway will be staying again in the future " [](https://expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![Motel 6 Roseburg, OR](https://images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/cd162212_y.jpg) ### Motel 6 Roseburg, OR 10/10 Excellent "Extremely satisfied! No complaints. " [](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information) ![Comfort Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "The front desk clerk was welcoming and made the check in process easy. The room has a super comfortable king size bed, microwave, fridge and a small table. Just what we needed for our late night. " [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Rosewood Inn and Suites](https://images.trvl-media.com/lodging/1000000/920000/920000/919945/198b0811_y.jpg) ### Rosewood Inn and Suites 10/10 Excellent "Amazing service. Jennifer was amazing. " [](https://expedia.ca/Roseburg-Hotels-Rosewood-Inn-And-Suites.h919945.Hotel-Information) ![Motel 6 Sutherlin, OR](https://images.trvl-media.com/lodging/1000000/430000/426000/425916/9d536feb_y.jpg) ### Motel 6 Sutherlin, OR 10/10 Excellent "Nice place reasonable price. Clean room, fun staff." 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