Title: Winchester B&B: Find the Best Bed and Breakfast from CA $170 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d12104.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d12104.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d12104.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d12104.Destination-Travel-Guides) ![Default HTG hotel image](https://media.expedia.com/media/content/shared/images/travelguides/sem-hotels-tablet.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Winchester from CA $170 ![](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 Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=12104&startDate=2025-12-26&endDate=2025-12-28&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester B&B ![Lobby sitting area](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/2fe245d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/56e5bf87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Traditional Room, 1 Double Bed, Terrace, City View | Front of property](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/2cace77a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Living area](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/d3109091.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Historical John Rast House Roseburg 10/10 Exceptional (48) "So glad we stayed here! The house was amazing if you like history. Our hosts were wonderful, breakfast was delicious and downtown is a short walk away. The property is gated and felt very safe. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $188 CA $248 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Roseburg-Hotels-Historical-John-Rast-House.h94859734.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/79000000/78430000/78425300/78425232/e143e97e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/79000000/78430000/78425300/78425232/387a3519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/79000000/78430000/78425300/78425232/e6c54321.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/79000000/78430000/78425300/78425232/a7408327.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Historic lodge across from Umpqua river Glide 10/10 Exceptional (34) "Beautiful property and great to deal with. Loved our stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joe CA $140 CA $170 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Idleyld-Park-Hotels-Historic-Lodge-Across-From-Umpqua-River.h78425232.Hotel-Information) ![Outdoor spa tub](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/eebe29d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/7782a7ed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 1 Queen Bed, Non Smoking, Courtyard View](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/652cca82.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Bungalow, 1 King Bed with Sofa bed, Kitchenette, Garden View | Private kitchenette](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/92d8f48b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### C.H. Bailey House Roseburg CA $341 CA $346 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Roseburg-Hotels-CH-Bailey-House.h121139975.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=2025-11-10&endDate=2025-11-11®ionId=12104&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.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d12104-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FWinchester-Bed-And-Breakfast.d12104-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Motel 6 Roseburg, OR](//images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/247b3334_y.jpg) ### Motel 6 Roseburg, OR 10/10 Excellent "Get ice mecsh" [](https://expedia.ca/Roseburg-Hotels-Motel-6-Roseburg.h1037746.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 "Very welcoming to pets! They even have a fenced-in dog area!! Loved it!" [](https://expedia.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information) ![Best Western Plus Hartford Lodge](//images.trvl-media.com/lodging/2000000/1790000/1784800/1784775/608fa78e_y.jpg) ### Best Western Plus Hartford Lodge 10/10 Excellent "Excellent friendly staff. The breakfast was above average and the room was clean." [](https://expedia.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information) ![Riverfront Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/16100/16066/81d2a043_y.jpg) ### Riverfront Inn Roseburg 10/10 Excellent "Nice view of the river and walking area to downtown " [](https://expedia.ca/Roseburg-Hotels-Riverfront-Inn-Roseburg.h16066.Hotel-Information) ![Comfort Inn Roseburg](//images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "Staff was attentive and friendly Pool and hot tub clean and relaxing Quiet yet easy on/ off highway Close to good dining options Breakfast options were good Room was very clean beds comfortable " [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![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 "Convenience store and In-n-out Burger close by. WiFi worked great." [](https://expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.Hotel-Information) ![Sleep Inn & Suites Roseburg North Near Medical Center](//images.trvl-media.com/lodging/1000000/540000/539600/539504/32f54617_y.jpg) ### Sleep Inn & Suites Roseburg North Near Medical Center 10/10 Excellent "Everything was wonderful. Breakfast was great easy in and out." [](https://expedia.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.Hotel-Information) ![Best Western Garden Villa Inn](//images.trvl-media.com/lodging/1000000/10000/7100/7049/eff8e6cb_y.jpg) ### Best Western Garden Villa Inn 10/10 Excellent "The room was clean except for the shower curtain. May have just been stained. But other than that, the room was very comfortable and the staff were very friendly" [](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information) ![Hampton Inn & Suites Roseburg](//images.trvl-media.com/lodging/23000000/22280000/22270800/22270751/df80a59c_y.jpg) ### Hampton Inn & Suites Roseburg 10/10 Excellent "The staff was incredible. They were kind to our little family, and made us feel right at home." [](https://expedia.ca/Roseburg-Hotels-Hampton-Inn-Suites-Roseburg.h22270751.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 82 | | --- | --- | | Accommodation | 2 B&B | | Lowest Price | CA $170 | | Highest Price | CA $346 | ## Frequently asked questions ### Searching for B&Bs in Winchester? > If you want to find a place to stay with fewer rooms than the traditional hotel and a more personalized environment, a B&B might be a great fit for your vacation to Winchester. When you want to explore some of the destination's attractions, North Umpqua River is worth a visit. ### Why should you consider B&Bs instead of traditional hotels? > B&Bs all have a unique charm. Whether it's a comfy common area with a fireplace or a sunlit breakfast nook to enjoy your morning cup of coffee, the tiny details are what make bed and breakfasts a home away from home. ### What are the top B&Bs in Winchester? > Here are some well-liked B&Bs in the surrounding area: [Charming Historic lodge across from Umpqua river](https://www.expedia.ca/Idleyld-Park-Hotels-Historic-Lodge-Across-From-Umpqua-River.h78425232.Hotel-Information): 17.1 mi (27.5 km) from the heart of Winchester.[Historical John Rast House](https://www.expedia.ca/Roseburg-Hotels-Historical-John-Rast-House.h94859734.Hotel-Information): 3 rooms. 4.7 mi (7.5 km) from the downtown core. [C.H. Bailey House](https://www.expedia.ca/Roseburg-Hotels-CH-Bailey-House.h121139975.Hotel-Information): 5 rooms. 9.7 mi (15.6 km) from the heart of downtown. Enjoy the free full breakfast and hot tub. ### When is the best time to book my B&B in Winchester? > When you're dreaming of a escape to Winchester, be sure to take into account the year-round temperatures. The hottest months are usually August and July with an average temp of 64°F, while the coldest months are December and February with an average of 41°F. Average annual precipitation for Winchester is 49 inches. ### What is there to do in Winchester? > If you want to check out some popular attractions in Winchester, you might enjoy a visit to North Umpqua River. 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