Title: Book the Best Oakland WINERY Hotels in 2025 | Expedia.ca [Hotels in Oakland](https://expedia.ca/Oakland-Hotels.d6023405.Travel-Guide-Hotels)[Vacation Rentals in Oakland](https://expedia.ca/Oakland-Vacation-Rentals.d6023405.Travel-Guide-VacationRentals)[Oakland Car Rentals](https://expedia.ca/Car-Rentals-In-Oakland.d6023405.Car-Rental-Guide)[Oakland Vacation Packages](https://expedia.ca/Oakland.d6023405.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/2/ed68325b2fbc7f8bca3a35bcaa3ea8d6.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by L Ru # Find Winery Hotels in Oakland, OR from CA $114 ![calendar shield illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation ![deals illustration](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) ![bed illustration](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Oakland Winery Hotels Tonight [Oct 4 - Oct 5](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-10-04&endDate=2025-10-05&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 5 - Oct 6](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-10-05&endDate=2025-10-06&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 10 - Oct 12](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-10-10&endDate=2025-10-12&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-10-17&endDate=2025-10-19&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Winery Hotels ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/91b3330a.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) ### Riverfront Inn Roseburg Roseburg 8.6/10 Excellent (1402) "We enjoyed our stay!" CA $130 CA $143 total includes taxes & fees Nov 1 - Nov 2 [](https://www.expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/3866516b.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) ![Individually decorated, individually furnished, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/41cd13e6.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 (1002) "Convenient location and easy parking." CA $142 CA $156 total includes taxes & fees Oct 19 - Oct 20 [](https://www.expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.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) ![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/1000000/20000/17800/17750/1a3bee3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn Roseburg Roseburg 8.2/10 Very good (1004) "The staff was exceptional " CA $152 CA $166 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89150000/89141600/89141559/ed28daf8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89150000/89141600/89141559/593911fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/90000000/89150000/89141600/89141559/8453f9eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/90000000/89150000/89141600/89141559/bf24431b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Cottage at Wild Goose Outpost Elkton 10/10 Exceptional (2) "Spacious, peaceful place. Room to relax, explore, wine taste, practice yoga. Well-appointed, including washer/dryer. Thank you Robynne." CA $195 CA $340 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Elkton-Hotels-The-Cottage-At-Wild-Goose-Outpost.h89141559.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) ![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) ![Business centre](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/e0f326ec.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Super 8 by Wyndham Roseburg Roseburg 7.8/10 Good (1003) "Was a good stay!" CA $104 CA $114 total includes taxes & fees Oct 12 - Oct 13 [](https://www.expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.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) ![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) ### 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 $198 CA $248 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) ![Property grounds](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630896/11d76b83.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 (33) "Extremely clean home in a safe neighborhood! We had everything we needed! Host was very kind and communicative! Would love to stay there again! " CA $161 CA $402 total includes taxes & fees Oct 8 - Oct 9 [](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) ![Terrace/patio](https://images.trvl-media.com/lodging/114000000/113520000/113518400/113518339/ab1adb13.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 (12) "great property" CA $301 CA $629 total includes taxes & fees Oct 6 - Oct 7 [](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/38000000/37920000/37912100/37912072/d29e7b69.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) ![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) ![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 $417 CA $640 total includes taxes & fees Oct 6 - Oct 7 [](https://www.expedia.ca/Roseburg-Hotels-Historic-Downtown-Luxurious-Apartment-Only-Steps-Away-From-Local-Restaurants.h37912072.Hotel-Information) ![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) ![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 $232 CA $544 total includes taxes & fees Oct 9 - Oct 10 [](https://www.expedia.ca/Winston-Hotels-The-Watusi-Place-A-Modern-Umpqua-Valley-Getaway.h78301309.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=2025-10-19&endDate=2025-10-20®ionId=6023405&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ## Top Oakland Hotel Reviews ![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) ![Riverfront Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043_y.jpg) ### Riverfront Inn Roseburg 10/10 Excellent "It is an older hotel. But was very clean (except the balcony). The office staff was fantastic, extra kudos to the night shift. Sorry didn't get her name. Bed was very comfortable and it was very relaxing sitting on the balcony after a long drive. I gave it overall 5 stars, can't beat the price. " [](https://expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.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 "Staff was amazing. The young man at the front desk went out of his way to make the best coffee for us. We felt very welcome and taken care of." [](https://expedia.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information) ![Motel 6 Roseburg, OR](//images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/247b3334_y.jpg) ### Motel 6 Roseburg, OR 10/10 Excellent "The cleanliness of this facility is outstanding ,the room is soft and clean " [](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information) ![Comfort Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "The staff was exceptional " [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Rice Hill Inn](//images.trvl-media.com/lodging/1000000/520000/517600/517554/1f954a05_y.jpg) ### Rice Hill Inn 10/10 Excellent "I've stayed here a few times. Always works out well" [](https://expedia.ca/Oakland-Hotels-Rice-Hill-Inn.h517554.Hotel-Information) ![Best Western Cottage Grove Inn](//images.trvl-media.com/lodging/1000000/20000/19100/19004/1c171023_y.jpg) ### Best Western Cottage Grove Inn 10/10 Excellent "Room clean, bed comfy, quiet. Hot and cold breakfast available. Definitely would stay again. " [](https://expedia.ca/Eugene-Hotels-Best-Western-Cottage-Grove-Inn.h19004.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 "Front desk very welcoming. Clean, perfect size property. Great breakfast. Loved the pool." [](https://expedia.ca/Roseburg-Hotels-Quality-Inn-Central-Roseburg.h663067.Hotel-Information) ![Cottage Grove Inn](//images.trvl-media.com/lodging/1000000/30000/22200/22131/b6b418c3_y.jpg) ### Cottage Grove Inn 10/10 Excellent "Room was clean and bed was comfortable. 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