Title: 20 Best B&B in Winston, OR - Bed and Breakfast from $186 | Expedia.com [Winston Travel Guide](https://expedia.com/Winston.dx6124402)[Hotels in Winston](https://expedia.com/Winston-Hotels.d6124402.Travel-Guide-Hotels)[Vacation Rentals in Winston](https://expedia.com/Winston-Vacation-Rentals.d6124402.Travel-Guide-VacationRentals)[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) ![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 ![](https://images.trvl-media.com/place/6090413/6a7f406c-e7ef-4707-844b-63d5d9268f55.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ## Check prices for these dates Next weekend [Apr 3 - Apr 5](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Apr 10 - Apr 12](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-04-10&endDate=2026-04-12&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Apr 24 - Apr 26](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-04-24&endDate=2026-04-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [May 22 - May 24](https://www.expedia.com/Hotel-Search?regionId=6124402&startDate=2026-05-22&endDate=2026-05-24&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winston bed & breakfast ![Porch](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/b23ccc36.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 King Bed, Non Smoking, Mountain View | Mountain view](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/16785050.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Bungalow, 1 King Bed with Sofa bed, Pets Allowed, Garden View | Iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/6d945c23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Double Room, 1 Queen Bed, Non Smoking, Mountain View | Mountain view](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/a42f81ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### C.H. Bailey House [](https://www.expedia.com/Roseburg-Hotels-CH-Bailey-House.h121139975.Hotel-Information) Roseburg 10/10 Exceptional (3 reviews) "Gorgeous setting. Lovely and exceptionally clean room - the bed was SO comfy. Really nice little touches too by the host, who was friendly and made us a great breakfast. Wish we could have stayed longer to explore the area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alice $183 nightly $186 total Mar 26 - Mar 27 Total with taxes and fees [](https://www.expedia.com/Roseburg-Hotels-CH-Bailey-House.h121139975.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/30b448a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/01b186c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/ae7d94af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden view](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/6a38b5a0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historical John Rast House [](https://www.expedia.com/Roseburg-Hotels-Historical-John-Rast-House.h94859734.Hotel-Information) Roseburg 10/10 Exceptional (49 reviews) "Loved this stay!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Rosemary $179 nightly $193 total Apr 6 - Apr 7 Total with taxes and fees [](https://www.expedia.com/Roseburg-Hotels-Historical-John-Rast-House.h94859734.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=2026-04-08&endDate=2026-04-09®ionId=6124402&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](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-Bed-And-Breakfast.d6124402-aaBedAndBreakfast.Travel-Guide-Accommodation)[ Sign up, it's free ](https://expedia.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinston-Bed-And-Breakfast.d6124402-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winston Hotel Reviews ![Motel 6 Roseburg, OR](https://images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/e0cf68d7_y.jpg) ### Motel 6 Roseburg, OR 10/10 Excellent "Clean, well-maintained, good food right next door. Parking lot was spacious enough to accommodate a 15 foot moving truck with no concerns about security." [](https://expedia.com/Roseburg-Hotels-Motel-6-Roseburg.h1037746.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 8/10 Good "The staff was incredibly friendly and accommodating the hotel was also a good price. I didn't like that the breakfast area was closed except during breakfast hours. It's nice to have somewhere to sit and/or eat meals of your own outside of the room. The dining area was also super small, but it sounds like they are working on expanding that. The pool was nice " [](https://expedia.com/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![Travelodge by Wyndham Canyonville](https://images.trvl-media.com/lodging/85000000/84100000/84099600/84099548/7b19a871_y.jpg) ### Travelodge by Wyndham Canyonville 10/10 Excellent "My kids loved our stay here. Room was very spacious and clean . Also the staffs are very friendly and always available to talk " [](https://expedia.com/Canyonville-Hotels-Canyonville-Inn.h84099548.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 2/10 Terrible "Place was a dump" [](https://expedia.com/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.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 8/10 Good "It was good " [](https://expedia.com/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Comfort Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/2194c7fa_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "Everything was just what we needed. Very happy and comfortable. The pool was great and the staff was great with keeping towels available for guests. " [](https://expedia.com/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Wolf Creek Inn & Tavern](https://images.trvl-media.com/lodging/31000000/30410000/30406600/30406572/ef45f74f_y.jpg) ### Wolf Creek Inn & Tavern 8/10 Good "Welcomed pets but I did not travel with pets" [](https://expedia.com/Wolf-Creek-Hotels-Wolf-Creek-Inn-Tavern.h30406572.Hotel-Information) ![The Lodge at Roseburg](https://images.trvl-media.com/lodging/1000000/30000/22800/22705/54e5b16d_y.jpg) ### The Lodge at Roseburg 6/10 Okay "Hot tub was out of service the whole stay,but river view was nice. Good location to walk to activities." [](https://expedia.com/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.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 "Nice spot Pet friendly Good breakfast" [](https://expedia.com/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information) ## Find out more about Winston ## Winston B&B information | Number of reviews | 52 | | ----------------- | ----- | | Accommodation | 2 B&B | | Lowest Price | $186 | | Highest Price | $193 | ## Frequently asked questions ### What is the nightly rate for a Bed & Breakfast in Winston? ### When is the best time to book a Bed & Breakfast in Winston? > If you're looking for a bustling atmosphere filled with activities, visiting in June is particularly popular. You can immerse yourself in the vibrant local culture, attend wine tastings, and partake in various outdoor festivals that celebrate the region's rich agricultural heritage. This energetic environment is superb for those who relish engaging with fellow travelers and locals. > > > For those seeking a more budget-friendly experience, consider planning your visit in November. This month offers a more tranquil environment, with fewer crowds and the opportunity to enjoy the beautiful fall landscapes. The crisp air and autumn colors create a picturesque backdrop for leisurely vineyard tours or cozy evenings by the fireplace in your B&B. ### What is the difference between a Winston B&B and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - Other - [Hotels near South Umpqua River ](https://www.expedia.com/South-Umpqua-River-Hotels.0-l684502648556560384-0.Travel-Guide-Filter-Hotels) - [Hotels near Wildlife Safari ](https://www.expedia.com/Wildlife-Safari-Hotels.0-l6090413-0.Travel-Guide-Filter-Hotels) - [Hotels near Abacela Winery ](https://www.expedia.com/Abacela-Winery-Hotels.0-l553248621532642236-0.Travel-Guide-Filter-Hotels) - [Hotels near Spangler Vineyards ](https://www.expedia.com/Spangler-Vineyards-Hotels.0-l553248621532642240-0.Travel-Guide-Filter-Hotels) - [Hotels near Pyrenees Vineyard & Cellars ](https://www.expedia.com/Pyrenees-Vineyard-Cellars-Hotels.0-l553248621532642239-0.Travel-Guide-Filter-Hotels) - [Hotels near Douglas County Museum of History and Natural History ](https://www.expedia.com/Douglas-County-Museum-Of-History-And-Natural-History-Hotels.0-l553248621532642241-0.Travel-Guide-Filter-Hotels) - 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[Pyrenees Vineyard & Cellars ](https://www.expedia.com/Pyrenees-Vineyard-Cellars-Myrtle-Creek.d553248621532642239.Vacation-Attraction) - [Douglas County Museum of History and Natural History ](https://www.expedia.com/Douglas-County-Museum-Of-History-And-Natural-History-Roseburg.d553248621532642241.Vacation-Attraction) - [Stewart Park ](https://www.expedia.com/Stewart-Park-Roseburg.d553248621561869686.Vacation-Attraction) - [Visit Roseburg ](https://www.expedia.com/Roseburg.dx6054633) - [Roseburg Vacations ](https://www.expedia.com/Roseburg.d6054633.Destination-Travel-Guides) - [Car rentals near Wildlife Safari ](https://www.expedia.com/Car-Rentals-In-Wildlife-Safari.d6090413.Car-Rental-Guide) - [Car rentals near Dillard ](https://www.expedia.com/Car-Rentals-In-Dillard.d553248635974902980.Car-Rental-Guide) - [Car rentals near Green ](https://www.expedia.com/Car-Rentals-In-Green.d553248634983112906.Car-Rental-Guide) - [Car rentals near Roseburg ](https://www.expedia.com/Car-Rentals-In-Roseburg.d6054633.Car-Rental-Guide) - 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