Title: Winchester B&B: Find the Best Bed and Breakfast | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d3000435714.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d3000435714.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d3000435714.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d3000435714.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 [Feb 13 - Feb 15](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-02-13&endDate=2026-02-15&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-02-20&endDate=2026-02-22&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Mar 6 - Mar 8](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-03-06&endDate=2026-03-08&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Apr 3 - Apr 5](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-04-03&endDate=2026-04-05&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Winchester bed & breakfast ![Front of property](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/64356a87.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/fff007e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/09335ad8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/77000000/76960000/76952700/76952694/9275be3b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa DeWolf [](https://www.expedia.ca/Jacksonville-Hotels-Villa-DeWolf.h76952694.Hotel-Information) Jacksonville 10/10 Exceptional (11 reviews) "If you want the kindest hospitality, delicious breakfast and a memorable experience at a gorgeous historical home instead of a generic hotel, you must stay here!" ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Catherine [](https://www.expedia.ca/Jacksonville-Hotels-Villa-DeWolf.h76952694.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=2026-02-20&endDate=2026-02-21®ionId=3000435714&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.d3000435714-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.d3000435714-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Sleep Inn & Suites South Jacksonville](https://images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg) ### Sleep Inn & Suites South Jacksonville 10/10 Excellent "Clean, quiet and comfortable. Have stayed many times and will continue. " [](https://expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Green Acres Hotel](https://images.trvl-media.com/lodging/10000000/9990000/9986700/9986625/a368327c_y.jpg) ### Green Acres Hotel 10/10 Excellent "Highly recommend. Great staff. Friendly customer service. Would stay again for sure. " [](https://expedia.ca/Pittsfield-Hotels-Green-Acres-Hotel.h9986625.Hotel-Information) ![Audrey's Abode ](https://images.trvl-media.com/lodging/104000000/103430000/103428500/103428480/w449h683x287y0-7464266c_y.jpg) ### Audrey's Abode 10/10 Excellent "If you love the country life, or have lived in the country for awhile, this place will bring you right back to it. Absolutely amazing, in all ways. Will be back again. Thank you! " [](https://expedia.ca/Jacksonville-Hotels-Audreys-Abode.h103428480.Hotel-Information) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](https://images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 10/10 Excellent "Clean room and great breakfast." [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![Quality Inn Jacksonville near I-72](https://images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg) ### Quality Inn Jacksonville near I-72 10/10 Excellent "The pool was warm!! The room was nice and clean .. The water pressure in the showers along with the soap that was free was amazing .. for a cheap rate you couldn’t beat this hotel " [](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Hampton Inn Jacksonville](https://images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg) ### Hampton Inn Jacksonville 10/10 Excellent "Clean room. Great friendly staff. " [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Monroe Street Suites](https://images.trvl-media.com/lodging/18000000/17050000/17047300/17047233/7fa649ae_y.jpg) ### Monroe Street Suites 10/10 Excellent "Great accomodations and concept for a small town. Much better than staying in a low budget chain hotel." [](https://expedia.ca/Pittsfield-Hotels-Monroe-Street-Suites.h17047233.Hotel-Information) ![Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee.](https://images.trvl-media.com/lodging/34000000/33300000/33294600/33294577/3245f16c_y.jpg) ### Peace on the Prairie Too - Tiny House, Pets Allowed, No cleaning fee. 10/10 Excellent "Kevin was an excellent host and the house on the prairie was exactly what we needed after a long day of travel. We were surprised with fresh baked cookies upon arrival.The house was very cozy and walking the trails of the prairie was great for our pup. We would definitely stay here again the future!" [](https://expedia.ca/Murrayville-Hotels-Peace-On-The-Prairie-Too-Tiny-House.h33294577.Hotel-Information) ![Best Western Jacksonville Inn](https://images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg) ### Best Western Jacksonville Inn 10/10 Excellent "Check-in was easy! No hassles! Room is clean and the TV works😊" [](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 11 | | ----------------- | ----- | | Accommodation | 2 B&B | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### Searching for B&Bs in Winchester? ### How do you know if a B&B is the right choice for your stay? ### What are the best bed and breakfasts in Winchester? ### When should I stay at a B&B in Winchester? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - More ways to book - [Alsey Hotels ](https://www.expedia.ca/Alsey-Hotels.d3000346086.Travel-Guide-Hotels) - [Apartments in Arcadia ](https://www.expedia.ca/Arcadia-Apartments.d553248635975871406-aaApartments.Travel-Guide-Accommodation) - [Cabin Rentals in Arenzville ](https://www.expedia.ca/Arenzville-Cabins.d3000346095-aaCabins.Travel-Guide-Accommodation) - [Arenzville Hotels ](https://www.expedia.ca/Arenzville-Hotels.d3000346095.Travel-Guide-Hotels) - 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