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://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 - ![](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 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Nov 21 - Nov 23](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-11-21&endDate=2025-11-23&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=3000435714&startDate=2026-01-02&endDate=2026-01-04&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester B&B ![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/77000000/76960000/76952700/76952694/0778f0b6.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/fff007e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Villa DeWolf Jacksonville 10/10 Exceptional (10) "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=2025-11-19&endDate=2025-11-20®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](//images.trvl-media.com/lodging/24000000/23840000/23831900/23831866/e80734a3_y.jpg) ### Sleep Inn & Suites 10/10 Excellent "Quite and very pleasing staff." [](https://expedia.ca/Springfield-Hotels-Sleep-Inn-Suites.h23831866.Hotel-Information) ![Best Western Jacksonville Inn](//images.trvl-media.com/lodging/1000000/130000/124300/124218/4f58843e_y.jpg) ### Best Western Jacksonville Inn 10/10 Excellent "I booked my room in advance,however I couldn't get in until 3pm! When check-out time is 11am! I didn't like that at all." [](https://expedia.ca/Springfield-Hotels-Best-Western-Jacksonville-Inn.h124218.Hotel-Information) ![William Watson Hotel](//images.trvl-media.com/lodging/7000000/6660000/6659600/6659525/080807c1_y.jpg) ### William Watson Hotel 10/10 Excellent "Everything about our stay was great. We will stay here again. The parking was good, as it was in front of the building. The restaurant was excellent." [](https://expedia.ca/Pittsfield-Hotels-William-Watson-Hotel.h6659525.Hotel-Information) ![Super 8 by Wyndham Jacksonville](//images.trvl-media.com/lodging/1000000/130000/123200/123170/52a6b400_y.jpg) ### Super 8 by Wyndham Jacksonville 10/10 Excellent "Good service " [](https://expedia.ca/Springfield-Hotels-Super-8-By-Wyndham-Jacksonville.h123170.Hotel-Information) ![Hampton Inn Jacksonville](//images.trvl-media.com/lodging/2000000/1380000/1376300/1376212/eab445e9_y.jpg) ### Hampton Inn Jacksonville 10/10 Excellent "My stay was great! Relaxing after a full day of work. But the best part of the trip was how wonderful your staff treated me! Madison was awesome and so kind! She offered great advice on local sites, restaurants and answered my queries with great enthusiasm. I missed her on her days off! So glad she was at the front desk the day I checked in! Also, I met another lady while staying here and we are now friends! See the attached picture of all of us… " [](https://expedia.ca/Springfield-Hotels-Hampton-Inn-Jacksonville.h1376212.Hotel-Information) ![Quality Inn Jacksonville near I-72](//images.trvl-media.com/lodging/1000000/480000/474300/474237/aba9334b_y.jpg) ### Quality Inn Jacksonville near I-72 10/10 Excellent "Easy check in and out very personable and friendly staff" [](https://expedia.ca/Springfield-Hotels-Quality-Inn.h474237.Hotel-Information) ![Holiday Inn Express Hotel & Suites Jacksonville by IHG](//images.trvl-media.com/lodging/2000000/1800000/1793100/1793078/46171e6f_y.jpg) ### Holiday Inn Express Hotel & Suites Jacksonville by IHG 10/10 Excellent "Didnt make it to breakfast but could still obtain banana and yoghurt. This was super nice of them. Had kecard glutch but Chris the evening desk man literally ran upstairs after rescanning ours to check that it worked. Beds were very comfy. Wood surfaces were a little worn...a minor flaw." [](https://expedia.ca/Springfield-Hotels-Holiday-Inn-Express-Hotel-Suites-Jacksonville.h1793078.Hotel-Information) ![PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods!](//images.trvl-media.com/lodging/35000000/34590000/34582500/34582445/3f150da0_y.jpg) ### PICKLEBALL, Heated Pool, Game Room, Outdoor Oasis, Tennis, Basketball, & woods! 10/10 Excellent "Becky and Dave are excellent hosts. We had the best time. The 3 six year olds brought their bikes and had the best time pretending the front driveway was a race track. If you want to make great memories with your family I would highly recommend this house. " [](https://expedia.ca/Pittsfield-Hotels-PICKLEBALL.h34582445.Hotel-Information) ![Baymont by Wyndham Jacksonville](//images.trvl-media.com/lodging/2000000/1310000/1304400/1304355/w3837h2569x3y3-79e6a5e0_y.jpg) ### Baymont by Wyndham Jacksonville 10/10 Excellent "Everything new and clean " [](https://expedia.ca/Springfield-Hotels-Baymont-By-Wyndham-Jacksonville.h1304355.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 10 | | --- | --- | | Accommodation | 2 B&B | | Lowest Price | | | Highest Price | | ## Frequently asked questions ### Searching for B&Bs in Winchester? > If you want to find an accommodation with fewer rooms than a hotel and an intimate environment, a bed and breakfast might be just the right fit for your vacation to Winchester. ### How do you know if a B&B is the right choice for your stay? > With attentive service, opportunities to interact with the owner, and tasty breakfasts, B&Bs offer a unique setting. ### What are the best bed and breakfasts in Winchester? > Here are some B&Bs in the area: [Villa DeWolf](https://www.expedia.ca/Jacksonville-Hotels-Villa-DeWolf.h76952694.Hotel-Information): 4 rooms. 13.5 mi (21.8 km) from the heart of Winchester. Enjoy the free cooked breakfast and designer toiletries. [Blessings on State Bed & Breakfast](https://www.expedia.ca/Springfield-Hotels-Blessings-On-State-Bed-Breakfast.h19824847.Hotel-Information): 2 rooms. 13.3 mi (21.4 km) from the downtown core. Enjoy the designer toiletries and spa. ### When should I stay at a B&B in Winchester? > When you're dreaming of a trip to Winchester, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August with an average temp of 73°F, while the coldest months are January and February with an average of 35°F. 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