Title: Winchester B&B: Find the Best Bed and Breakfast from CA $244 | 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://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Winchester from CA $244 - ![](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 ## Our top choices for Winchester bed & breakfast ![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) ![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) ![Garden](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/56e5bf87.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 [](https://www.expedia.ca/Roseburg-Hotels-Historical-John-Rast-House.h94859734.Hotel-Information) 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 $185 CA $244 total includes taxes & fees Dec 22 - Dec 23 [](https://www.expedia.ca/Roseburg-Hotels-Historical-John-Rast-House.h94859734.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) ![Front of property](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/8e1c559d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/7ecc2eda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Indoor wedding](https://images.trvl-media.com/lodging/122000000/121140000/121140000/121139975/de34e48d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### C.H. Bailey House [](https://www.expedia.ca/Roseburg-Hotels-CH-Bailey-House.h121139975.Hotel-Information) Roseburg CA $356 CA $361 total includes taxes & fees Jan 2 - Jan 3, 2026 [](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=2026-01-04&endDate=2026-01-05®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 ![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 "Wonderful friendly greeting. Helpful, reminded me of the hours of pool, breakfast etc. The room was clean with attention to detail." [](https://expedia.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information) ![Comfort Inn Roseburg](https://images.trvl-media.com/lodging/1000000/20000/17800/17750/61f465bf_y.jpg) ### Comfort Inn Roseburg 10/10 Excellent "Staff was amazing and room was clean and comfortable " [](https://expedia.ca/Roseburg-Hotels-Comfort-Inn.h17750.Hotel-Information) ![Motel 6 Sutherlin, OR](https://images.trvl-media.com/lodging/1000000/430000/426000/425916/9d536feb_y.jpg) ### Motel 6 Sutherlin, OR 10/10 Excellent "Yes" [](https://expedia.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information) ![Rosewood Inn and Suites](https://images.trvl-media.com/lodging/1000000/920000/920000/919945/198b0811_y.jpg) ### Rosewood Inn and Suites 10/10 Excellent "Great!" [](https://expedia.ca/Roseburg-Hotels-Rosewood-Inn-And-Suites.h919945.Hotel-Information) ![Hampton Inn & Suites Roseburg](https://images.trvl-media.com/lodging/23000000/22280000/22270800/22270751/df80a59c_y.jpg) ### Hampton Inn & Suites Roseburg 10/10 Excellent "Welcoming staff, clean room, comfort, easy access to freeway and shopping." [](https://expedia.ca/Roseburg-Hotels-Hampton-Inn-Suites-Roseburg.h22270751.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 "Yes everything was good" [](https://expedia.ca/Roseburg-Hotels-Quality-Inn-Central-Roseburg.h663067.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 "Clean room & staff were very nice. " [](https://expedia.ca/Roseburg-Hotels-Super-8-By-Wyndham-Roseburg.h159048.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 "Comfort,beautiful setting and great breakfasts " [](https://expedia.ca/Roseburg-Hotels-Holiday-Inn-Express-Roseburg.h22705.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 "Staff was awesome!" [](https://expedia.ca/Roseburg-Hotels-Best-Western-Garden-Villa-Inn.h7049.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 48 | | ----------------- | ------- | | Accommodation | 3 B&B | | Lowest Price | CA $244 | | Highest Price | CA $361 | ## Frequently asked questions ### Searching for B&Bs in Winchester? ### Why should you consider B&Bs instead of traditional hotels? ### What are the top B&Bs in Winchester? ### When is the best time to book my B&B in Winchester? ### What is there to do in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Other - More ways to book - [Cabin Rentals in Canyonville ](https://www.expedia.ca/Canyonville-Cabins.d183835-aaCabins.Travel-Guide-Accommodation) - [Condo Rentals in Canyonville ](https://www.expedia.ca/Canyonville-Condos.d183835-aaCondos.Travel-Guide-Accommodation) - [Cheap Hotels in Canyonville ](https://www.expedia.ca/Canyonville-Hotels-Cheap-Hotels.0-0-d183835-tCheapHotels.Travel-Guide-Filter-Hotels) - 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