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) ![An old covered bridge less than two miles off Highway 138. Worth a quick detour.](https://images.trvl-media.com/place/6023405/dc1205d1-5076-4b12-8f4c-228ec6519dc1.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by L Ru # Find Winery Hotels in Oakland, OR - ![](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 Oakland Winery Hotels Tonight [Nov 23 - Nov 24](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-11-23&endDate=2025-11-24&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Nov 24 - Nov 25](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-11-24&endDate=2025-11-25&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-11-28&endDate=2025-11-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6023405&startDate=2025-12-05&endDate=2025-12-07&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Oakland Winery Hotels ![Superior Room, 1 King Bed](https://images.trvl-media.com/lodging/1000000/30000/22200/22131/b6b418c3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Room, 1 King Bed | Room amenity](https://images.trvl-media.com/lodging/1000000/30000/22200/22131/a5661a58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior detail](https://images.trvl-media.com/lodging/1000000/30000/22200/22131/ab67ede1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/30000/22200/22131/4e81640d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cottage Grove Inn Cottage Grove 8.8/10 Excellent (1005) "Second stay here very clean and friendly " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jo CA $126 CA $141 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Eugene-Hotels-Cottage-Grove-Inn.h22131.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) ![Business centre](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/e0f326ec.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 (1003) "Courteous staff, good breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Thomas CA $92 CA $101 total includes taxes & fees Nov 25 - Nov 26 [](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) ![Lobby](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/95d13c97.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) ### 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 $128 CA $141 total includes taxes & fees Dec 7 - Dec 8 [](https://www.expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/6950d5ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Riverfront Inn Roseburg Roseburg 8.6/10 Excellent (1422) "Great park, walkable 24 hour stay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julie [](https://www.expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.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) ![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) ![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) ### SureStay by Best Western Roseburg Roseburg 8.0/10 Very good (1003) "All the sleep inne we stayed at were very nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Patrick J CA $111 CA $122 total includes taxes & fees Nov 30 - Dec 1 [](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) ![Exterior](https://images.trvl-media.com/lodging/43000000/42980000/42977900/42977823/b0dce006.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" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) SharonLee S. CA $274 CA $343 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Roseburg-Hotels-Vrbo-Property.h42977823.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) ![Interior](https://images.trvl-media.com/lodging/107000000/106920000/106918700/106918670/242efe42.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 $108 CA $167 total includes taxes & fees Nov 24 - Nov 25 [](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/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) ![Interior](https://images.trvl-media.com/lodging/84000000/83640000/83630900/83630896/216da08d.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 (36) "This place is great. We have stayed multiple times. Will continue to come back here when in the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Benjamin B. CA $156 CA $407 total includes taxes & fees Nov 25 - Nov 26 [](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/39000000/38320000/38315200/38315160/a698d623.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) ![Interior](https://images.trvl-media.com/lodging/39000000/38320000/38315200/38315160/d1ffc9b2.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!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) CARISSA F. CA $281 CA $476 total includes taxes & fees Nov 24 - Nov 25 [](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/114000000/113520000/113518400/113518339/c59f6e86.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) ![Interior](https://images.trvl-media.com/lodging/114000000/113520000/113518400/113518339/47728b62.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) "great property" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mai CA $305 CA $640 total includes taxes & fees Nov 28 - Nov 29 [](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=2025-12-07&endDate=2025-12-08®ionId=6023405&adults=2&location_highlights_explore=winery&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AFFINITY_BF_PROMO_6023405) ## Top Oakland Hotel Reviews ![Motel 6 Sutherlin, OR](https://images.trvl-media.com/lodging/1000000/430000/426000/425916/9d536feb_y.jpg) ### Motel 6 Sutherlin, OR 10/10 Excellent "We were travling from wahsington back to california with our two new to us, fur babys. so having a pet friendly place to stay was imperative. We felt very welcomed and loved that they welcomed our pets as well. the room was very clean and conveniently just off of I5.. The bonus was 50 tesla super chargers just on the other side of I5:)" [](https://expedia.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information) ![Cottage Grove Inn](https://images.trvl-media.com/lodging/1000000/30000/22200/22131/b6b418c3_y.jpg) ### Cottage Grove Inn 10/10 Excellent "Clean room. Basic, worked just fine for us." [](https://expedia.ca/Eugene-Hotels-Cottage-Grove-Inn.h22131.Hotel-Information) ![Comfort Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "Clean nice staff " [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Best Western Plus Hartford Lodge](https://images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/608fa78e_y.jpg) ### Best Western Plus Hartford Lodge 10/10 Excellent "Kind staff, great room, and awesome breakfast!" [](https://expedia.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.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 "They had a couple people work on the front desk so check in was quick and painless. The room was clean. The water was hot bed was comfortable everything you want from a hotel." [](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information) ![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 "Courteous staff, good breakfast." [](https://expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.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 "All Good" [](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information) ![Rice Hill Inn](https://images.trvl-media.com/lodging/1000000/520000/517600/517554/1f954a05_y.jpg) ### Rice Hill Inn 10/10 Excellent "Nice clean quiet room with very helpful staff. Would stay again." [](https://expedia.ca/Oakland-Hotels-Rice-Hill-Inn.h517554.Hotel-Information) ![Quality Inn Central Roseburg](https://images.trvl-media.com/lodging/1000000/670000/663100/663067/f699f1d4_y.jpg) ### Quality Inn Central Roseburg 10/10 Excellent "Room was spotless... Check in staff was excellent. Very happy with my stay. 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