Title: Winchester B&B: Find the Best Bed and Breakfast from CA $243 | 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) ![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.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 Next weekend [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=12104&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.ca/Hotel-Search?regionId=12104&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.ca/Hotel-Search?regionId=12104&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.ca/Hotel-Search?regionId=12104&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 Winchester 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 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) ![Luxury Bungalow, 1 King Bed with Sofa bed, Pets Allowed, Garden View](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 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) ### C.H. Bailey House [](https://www.expedia.ca/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 CA $266 CA $270 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/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) ![Reception](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/ae7d94af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Television](https://images.trvl-media.com/lodging/95000000/94860000/94859800/94859734/0172991e.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.ca/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 CA $184 CA $243 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/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.ca/Hotel-Search?startDate=2026-04-07&endDate=2026-04-08®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](https://images.trvl-media.com/lodging/2000000/1040000/1037800/1037746/e0cf68d7_y.jpg) ### Motel 6 Roseburg, OR 6/10 Okay "Not that clean." [](https://expedia.ca/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.ca/Roseburg-Hotels-Sleep-Inn-Suites-Roseburg-North-Near-Medical-Center.h539504.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.ca/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.ca/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.ca/Roseburg-Hotels-Comfort-Inn.h17750.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.ca/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.ca/Roseburg-Hotels-Best-Western-Plus-Hartford-Lodge.h1784775.Hotel-Information) ![Motel 6 Sutherlin, OR](https://images.trvl-media.com/lodging/1000000/430000/426000/425916/1f1bce8d_y.jpg) ### Motel 6 Sutherlin, OR 6/10 Okay "Clean, but bare bones. No facial tissues in the room (cutback from Motel 6 purchase). No breakfast" [](https://expedia.ca/Roseburg-Hotels-Motel-6-Sutherlin.h425916.Hotel-Information) ![The Ranch Motel](https://images.trvl-media.com/lodging/91000000/90330000/90329500/90329493/f903acf4_y.jpg) ### The Ranch Motel 10/10 Excellent "What a unique little spot! Individual A-frame units feel like camping cabins but with clean modern facilities like a hotel room. Very affordable and conveniently located for anyone traveling along the I-5 corridor. The owners are very friendly and great hosts! The chickens that strolled around the property (and came to greet me) were an added bonus to the charming rustic atmosphere of the location. A travel center (with a Subway and a Dennys) ensures that anything you may need during your stay is within walking distance. Thanks Tim - you guys really have something here - I'll be 'starring' this location for my future travels!" [](https://expedia.ca/Oakland-Hotels-The-Ranch-Motel-By-OYO-Oakland-I-5.h90329493.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 52 | | ----------------- | ------- | | Accommodation | 3 B&B | | Lowest Price | CA $243 | | Highest Price | CA $270 | ## 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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