Title: Winston Vacation Rentals from $112: Search Short-Term Rentals | Expedia.com [Winston Travel Guide](https://expedia.com/Winston.dx6124402)[Hotels in Winston](https://expedia.com/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Flights to Winston](https://expedia.com/Cheap-Flights-To-Winston.d6124402.Travel-Guide-Flights)[Things to do in Winston](https://expedia.com/Things-To-Do-In-Winston.d6124402.Travel-Guide-Activities)[Car Rentals in Winston](https://expedia.com/Car-Rentals-In-Winston.d6124402.Car-Rental-Guide)[Winston Vacation Packages](https://expedia.com/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_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates In two weeks [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-04-24&endDate=2026-04-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jun 5 - Jun 7](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-06-05&endDate=2026-06-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In three months [Jul 3 - Jul 5](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-07-03&endDate=2026-07-05&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In four months [Jul 31 - Aug 2](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-07-31&endDate=2026-08-02&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) ![Deluxe Apartment, City View | 1 bedroom, blackout drapes, soundproofing, iron/ironing board](https://images.trvl-media.com/lodging/107000000/106630000/106623500/106623497/63bf9cb7.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) ![Exterior](https://images.trvl-media.com/lodging/107000000/106630000/106623500/106623497/4742db7f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bell Sister Flats [](https://www.expedia.com/Roseburg-Hotels-Bell-Sister-Flats.h106623497.Hotel-Information) Roseburg $368 nightly $403 total Apr 13 - Apr 14 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-04-21&endDate=2026-04-22®ionId=6124402&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ## Find vacation rentals that suit your style Cabins [](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=CABIN) Private vacation homes [](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VACATION_HOME) Cottages [](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=COTTAGE) Apartments [](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APARTMENT) Villas [](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=VILLA) Aparthotels [](https://www.expedia.com/Hotel-Search?destination=Winston%2C+Oregon%2C+United+States+of+America®ionId=6124402&latLong=43.122338%2C-123.412572&adults=2&startDate=2026-07-06&d1=2026-07-06&endDate=2026-07-09&d2=2026-07-09&lodging=APART_HOTEL) ![](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.com/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals) ## Top Winston Hotel Reviews ![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 "Easy access to the Freeway store close by. The staff was great, the pool and hot tub so nice, a great way to end a day of travel. We will definitely stop here on our trip down and back to Yuma next season." [](https://expedia.com/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Motel 6 Sutherlin, OR](https://images.trvl-media.com/lodging/1000000/430000/426000/425916/1f1bce8d_y.jpg) ### Motel 6 Sutherlin, OR 2/10 Terrible "Didn't even know a pool existed, and my AC didn't work In my room, it was hot as heck in our room made it a miserable stay and had problems with our TV had to have someone come up and switch out the remote and then the same thing happened got tired of having to ask the front desk to come assist, also my pillows didn't even have pillow cases on them." [](https://expedia.com/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information) ![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 "Clean" [](https://expedia.com/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![Best Western Plus Hartford Lodge](https://images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/8b128a12_y.jpg) ### Best Western Plus Hartford Lodge 10/10 Excellent "Staff was incredibly kind and helpful, breakfast was great and the room was clean and comfortable. We loved our stay." [](https://expedia.com/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information) ![Riverfront Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/16100/16066/9d919bda_y.jpg) ### Riverfront Inn Roseburg 8/10 Good "The staff were very helpful and friendly " [](https://expedia.com/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information) ![Travelodge by Wyndham Canyonville](https://images.trvl-media.com/lodging/85000000/84100000/84099600/84099548/7b19a871_y.jpg) ### Travelodge by Wyndham Canyonville 8/10 Good "Very friendly staff " [](https://expedia.com/Canyonville-Hotels-Canyonville-Inn.h84099548.Hotel-Information) ![Comfort Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/2194c7fa_y.jpg) ### Comfort Inn Roseburg 8/10 Good "Clean spacious room, friendly, helpful staff. There were some problems with the coffee, juice and waffle machines. Not sure what was going on there." [](https://expedia.com/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Motel 6 Roseburg, OR](https://images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/e0cf68d7_y.jpg) ### Motel 6 Roseburg, OR 6/10 Okay "The rooms need a complete renovation and new beds." [](https://expedia.com/Roseburg-Hotels-Motel-6-Roseburg.h1037746.Hotel-Information) ![The Lodge at Roseburg](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/54e5b16d_y.jpg) ### The Lodge at Roseburg 10/10 Excellent "The breakfast was great. Love the hot options. Didn't get to use the pool. There was a large family in it for hours. They definitely sounded like they were having a great time. " [](https://expedia.com/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.Hotel-Information) ## Find out more about Winston **Everything you need to know about Winston vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winston vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on. There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winston vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. **Winston vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Winston. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Winston in high season. Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $112 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals! **How to find incredible deals on Winston rentals** At Expedia, we put the best Winston vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. To find some top Winston rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winston vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winston. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. ## Explore a world of travel with Expedia - Trending destinations on Expedia.com - All accommodation types in Winston ### Trending destinations on Expedia.com - [Destin Vacation Rentals ](https://www.expedia.com/Destin-Vacation-Rentals.d6906.Travel-Guide-VacationRentals) - [Panama City Vacation Rentals ](https://www.expedia.com/Panama-City-Beach-Vacation-Rentals.d8021.Travel-Guide-VacationRentals) - [Hilton Head Vacation Rentals ](https://www.expedia.com/Hilton-Head-Island-Vacation-Rentals.d601684.Travel-Guide-VacationRentals) - [Gulf Shores Vacation Rentals ](https://www.expedia.com/Gulf-Shores-Vacation-Rentals.d603078.Travel-Guide-VacationRentals) - [Key West Vacation Rentals ](https://www.expedia.com/Key-West-Vacation-Rentals.d1187.Travel-Guide-VacationRentals) - [Gatlinburg Vacation Rentals ](https://www.expedia.com/Gatlinburg-Vacation-Rentals.d7474.Travel-Guide-VacationRentals) - [Maui Vacation Rentals ](https://www.expedia.com/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Orlando Vacation Rentals ](https://www.expedia.com/Orlando-Vacation-Rentals.d178294.Travel-Guide-VacationRentals) - [Myrtle Beach Vacation Rentals ](https://www.expedia.com/Myrtle-Beach-Vacation-Rentals.d601685.Travel-Guide-VacationRentals) - [Orange Beach Vacation Rentals ](https://www.expedia.com/Orange-Beach-Vacation-Rentals.d9136.Travel-Guide-VacationRentals) - [Pigeon Forge Vacation Rentals ](https://www.expedia.com/Pigeon-Forge-Vacation-Rentals.d8264.Travel-Guide-VacationRentals) - [Ocean City Vacation Rentals ](https://www.expedia.com/Ocean-City-Vacation-Rentals.d9151.Travel-Guide-VacationRentals) - [Outer Banks Vacation Rentals ](https://www.expedia.com/Outer-Banks-Vacation-Rentals.d602135.Travel-Guide-VacationRentals) - [San Diego Vacation Rentals ](https://www.expedia.com/San-Diego-Vacation-Rentals.d3073.Travel-Guide-VacationRentals) - [Siesta Key Vacation Rentals ](https://www.expedia.com/Siesta-Key-Vacation-Rentals.d6881.Travel-Guide-VacationRentals) - [Galveston Vacation Rentals ](https://www.expedia.com/Galveston-Vacation-Rentals.d1341.Travel-Guide-VacationRentals) - [Clearwater Beach Vacation Rentals ](https://www.expedia.com/Clearwater-Beach-Vacation-Rentals.d10759.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals ](https://www.expedia.com/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Florida Keys Vacation Rentals ](https://www.expedia.com/Florida-Keys-Vacation-Rentals.d6023765.Travel-Guide-VacationRentals) - [Lake Tahoe Vacation Rentals ](https://www.expedia.com/South-Lake-Tahoe-Vacation-Rentals.d10150.Travel-Guide-VacationRentals) - [Lake of the Ozarks Vacation Rentals ](https://www.expedia.com/Lake-Ozark-Vacation-Rentals.d177772.Travel-Guide-VacationRentals) - [Florida Vacation Rentals ](https://www.expedia.com/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Hawaii Vacation Rentals ](https://www.expedia.com/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Michigan Vacation Rentals ](https://www.expedia.com/Destinations-In-Michigan.d224.Vacation-Rental-Destinations) - [Vacation Homes in Winston ](https://expedia.com/Winston-Private-Vacation-Homes.d6124402-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Apartments in Winston ](https://expedia.com/Winston-Apartments.d6124402-aaApartments.Travel-Guide-Accommodation) - [Motels in Winston ](https://expedia.com/Winston-Motels.d6124402-aaMotels.Travel-Guide-Accommodation) - [Cottages in Winston ](https://expedia.com/Winston-Cottages.d6124402-aaCottages.Travel-Guide-Accommodation) - [Farmstay in Winston ](https://expedia.com/Winston-Agritourism.d6124402-aaAgritourism.Travel-Guide-Accommodation) - [B&B in Winston ](https://expedia.com/Winston-Bed-And-Breakfast.d6124402-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Cabin Rentals in Winston ](https://expedia.com/Winston-Cabins.d6124402-aaCabins.Travel-Guide-Accommodation) - [Villas in Winston ](https://expedia.com/Winston-Villas.d6124402-aaVillas.Travel-Guide-Accommodation) - [Aparthotels in Winston ](https://expedia.com/Winston-Apart-Hotels.d6124402-aaApartHotels.Travel-Guide-Accommodation) - [RV Parks in Winston ](https://expedia.com/Winston-RV-Parks.d6124402-aaRVParks.Travel-Guide-Accommodation) - [Resorts in Winston ](https://expedia.com/Winston-Resorts.d6124402-aaResorts.Travel-Guide-Accommodation) - [Guest Houses in Winston ](https://expedia.com/Winston-Guest-Houses.d6124402-aaGuestHouses.Travel-Guide-Accommodation) - [Condo Rentals in Winston ](https://expedia.com/Winston-Condos.d6124402-aaCondos.Travel-Guide-Accommodation) ## Frequently asked questions ### Are there vacation rentals in Winston? 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