Title: Winston Vacation Rentals from CA $156: Short-Term Rentals for 2026 | Expedia.ca [Hotels in Winston](https://expedia.ca/Winston-Hotels.d6124402.Travel-Guide-Hotels)[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://images.trvl-media.com/place/6090413/6a7f406c-e7ef-4707-844b-63d5d9268f55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) Photo by Michelle Finseth ![](https://images.trvl-media.com/place/6090413/6a7f406c-e7ef-4707-844b-63d5d9268f55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](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 prices for these dates In two weeks [Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 29 - May 31](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2026-05-29&endDate=2026-05-31&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jun 26 - Jun 28](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2026-06-26&endDate=2026-06-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 24 - Jul 26](https://www.expedia.ca/Hotel-Search?regionId=6124402&startDate=2026-07-24&endDate=2026-07-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winston vacation rentals ![Deluxe Apartment, City View | Private kitchen](https://images.trvl-media.com/lodging/107000000/106630000/106623500/106623497/5569de9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/107000000/106630000/106623500/106623497/9f411763.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, City View](https://images.trvl-media.com/lodging/107000000/106630000/106623500/106623497/63bf9cb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment, City View | Living area](https://images.trvl-media.com/lodging/107000000/106630000/106623500/106623497/43e847fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bell Sister Flats [](https://www.expedia.ca/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information) Roseburg CA $395 CA $540 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Roseburg-Hotels-Bell-Sister-Flats.h106623497.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=2026-04-14&endDate=2026-04-15®ionId=6124402&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Private vacation homes [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VACATION_HOME) Aparthotels [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=APART_HOTEL) Cabins [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CABIN) Apartments [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=APARTMENT) Condos [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=CONDO) Villas [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=VILLA) Cottages [](https://www.expedia.ca/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-06-29&d1=2026-06-29&endDate=2026-07-02&d2=2026-07-02&lodging=COTTAGE) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in ](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals) ## Top Winston Hotel Reviews ![SureStay by Best Western Roseburg](https://images.trvl-media.com/lodging/1000000/540000/539600/539504/1c101170_y.jpg) ### SureStay by Best Western Roseburg 10/10 Excellent "I booked a pet room through expedia (only dogs allowed), but when I arrived they charged me another $15\. Whatever, it was worth it. The room was immaculate. In a pet room with carpet, it had no smell. Super clean. They have you sign a waiver that you'll clean up after your pet, and they're not allowed on the furniture, but that's why the place is so clean and the upholstery is intact. I can see why the deposit was mentioned in other reviews. They have a big grassy area for your dogs and it is very well lit at night so you feel safe. The mattress was very comfortable, super soft. To nitpick I wish the rooms had a regular thermostat for better regulation, the fridge could be colder, and the tv was really small. Also it is next to a freeway which can get noisy." [](https://expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![The Lodge at Roseburg](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/54e5b16d_y.jpg) ### The Lodge at Roseburg 2/10 Terrible "We have stayed here many times before and had a decent stay. Unfortunately, this was the worst one, and we won't be back. The staff gave us the keys to a room that was already occupied...we walked into someone else's room. Not only was that inappropriate, but also unsafe. I was worried that could happen to our room as well and at any point someone could come in to our room. I felt the staff did not handle this well at all and merely shrugged it off. They said a manager would contact me about compensation, but they never did... This was a huge mistake on their part and the manager should've done what they could to make sure we were comfortable. The breakfast was not stocked when we came down to eat. We waited for a bit to see if they would restock a few of the hot items and they never did. They also took away the pancake machine which our kids loved. Pretty disappointing trip..." [](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information) ![Motel 6 Roseburg, OR](https://images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/e0cf68d7_y.jpg) ### Motel 6 Roseburg, OR 10/10 Excellent "Nice, clean room. Friendly staff. Easy check-in and check-out. Great value for the price. Would recommend, especially if you're just looking for a quick overnight stay and don't need lots of amenities." [](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information) ![Super 8 by Wyndham Roseburg](https://images.trvl-media.com/lodging/1000000/160000/159100/159048/f15eab6a_y.jpg) ### Super 8 by Wyndham Roseburg 10/10 Excellent "Business trip" [](https://expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.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 "Clean room but floors are dirty, staff and breakfast and parking convenience is amazing " [](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information) ![Comfort Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/2194c7fa_y.jpg) ### Comfort Inn Roseburg 8/10 Good "We found the breakfast to be decent, the hot tub and pool were great, the staff was friendly and nice, although the room could have been cleaner and our room had a slight musty smell, but overall it was a great experience." [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Travelodge by Wyndham Canyonville](https://images.trvl-media.com/lodging/85000000/84100000/84099600/84099548/7b19a871_y.jpg) ### Travelodge by Wyndham Canyonville 2/10 Terrible "Didn’t expect the front desk person laughing at no reason at my arrival it felt really weird I did check in anyway I go out for a dinner and decided to just better check out and not spend a night there my bad choosing this one never again 👎" [](https://expedia.ca/Canyonville-Hotels-Canyonville-Inn.h84099548.Hotel-Information) ![Hampton Inn & Suites Roseburg](https://images.trvl-media.com/lodging/23000000/22280000/22270800/22270751/3b60422d_y.jpg) ### Hampton Inn & Suites Roseburg 10/10 Excellent "Great service, workout room and complimentary breakfast " [](https://expedia.ca/Roseburg-Hotels-Hampton-Inn-Suites-Roseburg.h22270751.Hotel-Information) ![Glendale Inn](https://images.trvl-media.com/lodging/122000000/121630000/121622500/121622492/2ace8063_y.jpg) ### Glendale Inn 2/10 Terrible "The room was dirty. Nasty stain on the sheets. No one in the office to get clean sheets. But I guess you get what you pay for. Bring your own bedding. " [](https://expedia.ca/Glendale-Hotels-Glendale-Inn.h121622492.Hotel-Information) ## Find out more about Winston You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded. As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winston. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. 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### What's the top vacation rental in Winston? ### How many vacation rentals will I find in Winston? ### What’s there to see and do in Winston? ### What’s a vacation rental in Winston like? ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points 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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