Title: Winchester B&B: Find the Best Bed and Breakfast from CA $172 | Expedia.ca [Hotels in Winchester](https://expedia.ca/Winchester-Hotels.d553248635975872164.Travel-Guide-Hotels)[Vacation Rentals in Winchester](https://expedia.ca/Winchester-Vacation-Rentals.d553248635975872164.Travel-Guide-VacationRentals)[Winchester Car Rentals](https://expedia.ca/Car-Rentals-In-Winchester.d553248635975872164.Car-Rental-Guide)[Winchester Vacation Packages](https://expedia.ca/Winchester.d553248635975872164.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 $172 ![](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 [Oct 17 - Oct 19](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-10-17&endDate=2025-10-19&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-10-24&endDate=2025-10-26&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-11-07&endDate=2025-11-09&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Winchester B&B ![Porch](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/244a9df9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Chesapeake Haven)](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/90041687.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/496ae4cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/c03fee2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn At The Canal Bed & Breakfast Chesapeake City 8.6/10 Excellent (504) "The property owner, Ed, was fabulous. I cannot say enough wonderful things about his hospitality and the Inn is in a perfect location." CA $239 CA $254 total includes taxes & fees Oct 15 - Oct 16 [](https://www.expedia.ca/Chesapeake-City-Hotels-Inn-At-The-Canal-Bed-Breakfast.h15082750.Hotel-Information) ![The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/2dabe54c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/a5510d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (Rodgers) | Bathroom](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/w491h206x3y3-e2361b9b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (O'Neill) | Living area](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/c3481ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vandiver Inn Havre De Grace 9.4/10 Exceptional (519) "Been to the Vandiver many times and are always pleasantly pleased." CA $192 CA $216 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Outdoor wedding area](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153614/d2030418.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153614/b29410be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153614/b1d27467.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free full breakfast](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153614/7def27c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Elk Forge B&B Inn & Day Spa Elkton 8.8/10 Excellent (179) "Very nice property it was a very good experience " CA $163 CA $172 total includes taxes & fees Oct 14 - Oct 15 [](https://www.expedia.ca/Elkton-Hotels-Elk-Forge-BB-Inn-Day-Spa.h1153614.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/33000000/32130000/32128100/32128064/43d46361.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/33000000/32130000/32128100/32128064/5467c090.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Tack Room](https://images.trvl-media.com/lodging/33000000/32130000/32128100/32128064/ac8685a8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/33000000/32130000/32128100/32128064/c1d4928e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn at Whitewing Farm West Chester 9.8/10 Exceptional (50) "Wonderful hosts - enjoyed our stay there!" CA $331 CA $368 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Exton-Hotels-The-Inn-At-Whitewing-Farm.h32128064.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3180000/3173700/3173628/53b7a14d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Individually decorated, individually furnished, desk, iron/ironing board](https://images.trvl-media.com/lodging/4000000/3180000/3173700/3173628/5e6db4bf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/4000000/3180000/3173700/3173628/948a6bf5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3180000/3173700/3173628/092c86af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairville Inn Chadds Ford 8.2/10 Very good (478) "Nice quiet place. My suite was beautiful. Breakfast was delicious every morning. " CA $364 CA $405 total includes taxes & fees Nov 13 - Nov 14 [](https://www.expedia.ca/Exton-Hotels-Fairville-Inn.h3173628.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=2025-10-27&endDate=2025-10-28®ionId=553248635975872164&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.d553248635975872164-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.d553248635975872164-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Winchester Hotel Reviews ![Sheraton Suites Wilmington Downtown](//images.trvl-media.com/lodging/1000000/10000/4700/4693/72ec9ef5_y.jpg) ### Sheraton Suites Wilmington Downtown 10/10 Excellent "Clean room, great service. Parking slots in the garage are extremely narrow for today’s cars." [](https://expedia.ca/Wilmington-Hotels-Sheraton-Suites-Wilmington-Downtown.h4693.Hotel-Information) ![Sonesta Select Newark Christiana Mall](//images.trvl-media.com/lodging/1000000/10000/2100/2091/5b01ae08_y.jpg) ### Sonesta Select Newark Christiana Mall 10/10 Excellent "It was perfect for a night of a ling day driving. Convenient and quite." [](https://expedia.ca/Wilmington-Hotels-Sonesta-Select-Newark.h2091.Hotel-Information) ![Fairfield Inn by Marriott Kennett Square Brandywine Valley](//images.trvl-media.com/lodging/3000000/2810000/2804200/2804110/06c01027_y.jpg) ### Fairfield Inn by Marriott Kennett Square Brandywine Valley 10/10 Excellent "We were in town for a wedding and our stay was a pleasure. Our room was well apportioned and the bed was very comfortable. We appreciated the healthy and delicious breakfast choices." [](https://expedia.ca/Exton-Hotels-Fairfield-Inn-By-Marriott-Kennett-Square-Brandywine-Valley.h2804110.Hotel-Information) ![Best Western Plus Newark/Christiana Inn](//images.trvl-media.com/lodging/1000000/910000/900500/900419/bb536b3a_y.jpg) ### Best Western Plus Newark/Christiana Inn 10/10 Excellent "Raymond at the front desk was so friendly and accommodating. He explained everything and made recommendations for food. He seriously deserves a raise!! " [](https://expedia.ca/Wilmington-Hotels-Best-Western-Plus-NewarkChristiana-Inn.h900419.Hotel-Information) ![Staybridge Suites Wilmington Downtown by IHG](//images.trvl-media.com/lodging/82000000/81880000/81875700/81875625/d8ff2a29_y.jpg) ### Staybridge Suites Wilmington Downtown by IHG 10/10 Excellent "New & clean.. friendly staff text communication for check out great breakfast " [](https://expedia.ca/Wilmington-Hotels-Staybridge-Suites-Wilmington-Downtown.h81875625.Hotel-Information) ![Red Roof Inn Perryville](//images.trvl-media.com/lodging/1000000/20000/11300/11260/a62f5bd3_y.jpg) ### Red Roof Inn Perryville 10/10 Excellent "Nicely redecorated, very clean and comfortable" [](https://expedia.ca/Perryville-Hotels-Red-Roof-Inn-Perryville.h11260.Hotel-Information) ![Hyatt Place Wilmington Riverfront](//images.trvl-media.com/lodging/35000000/34930000/34927700/34927626/a064dc72_y.jpg) ### Hyatt Place Wilmington Riverfront 10/10 Excellent "Great location on Riverfront" [](https://expedia.ca/Wilmington-Hotels-Hyatt-Place-Wilmington-Riverfront.h34927626.Hotel-Information) ![Comfort Inn & Suites Newark - Wilmington](//images.trvl-media.com/lodging/1000000/20000/12000/11904/ea219a4a_y.jpg) ### Comfort Inn & Suites Newark - Wilmington 10/10 Excellent "Staff was very friendly and energetic. Upon entering I was greeted with smiles and good characters who set me up my room for the night. The room itself was spacious and clean. Something about the environment was screaming for me to come back again. :)" [](https://expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information) ![Baymont by Wyndham Newark at University of Delaware](//images.trvl-media.com/lodging/1000000/50000/42000/41973/b371460e_y.jpg) ### Baymont by Wyndham Newark at University of Delaware 10/10 Excellent "Great hotel" [](https://expedia.ca/Wilmington-Hotels-Baymont-By-Wyndham-Newark-At-University-Of-Delaware.h41973.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 915 | | --- | --- | | Accommodation | 6 B&B | | Lowest Price | CA $172 | | Highest Price | CA $405 | ## Frequently asked questions ### Searching for B&Bs in Winchester? > If you want to find an accommodation with a small number of rooms and an intimate environment, a B&B may be the perfect thing for your getaway to Winchester. ### Are you thinking about B&Bs over traditional hotel rooms? > With attentive service, opportunities to meet other guests, and hearty breakfasts, B&Bs offer a truly one-of-a-kind environment. ### What are the best bed and breakfasts in Winchester? > Here are some B&Bs in the area: [Elk Forge B&B Inn & Day Spa](https://www.expedia.ca/Elkton-Hotels-Elk-Forge-BB-Inn-Day-Spa.h1153614.Hotel-Information): 14 rooms. 2.6 mi (4.2 km) from the heart of Winchester. Enjoy the free full breakfast and massage services. [Vandiver Inn](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information): 17 rooms. 14.6 mi (23.5 km) from the downtown core. Enjoy the free cooked breakfast and fireplace in the lobby. [Fairville Inn](https://www.expedia.ca/Exton-Hotels-Fairville-Inn.h3173628.Hotel-Information): 15 rooms. Situated 17.5 mi (28.1 km) from the heart of Winchester. Enjoy the free full breakfast and massage services. [The Inn at Whitewing Farm](https://www.expedia.ca/Exton-Hotels-The-Inn-At-Whitewing-Farm.h32128064.Hotel-Information): 10 rooms. 17.8 mi (28.7 km) from the heart of downtown. Enjoy the free full breakfast and outdoor pool. [Inn At The Canal Bed & Breakfast](https://www.expedia.ca/Chesapeake-City-Hotels-Inn-At-The-Canal-Bed-Breakfast.h15082750.Hotel-Information): 6 rooms. Located 10.4 mi (16.7 km) from the core of Winchester. Enjoy the free full breakfast and library. ### When is the best time to stay at a B&B in Winchester? > When you're planning your stay in Winchester, be sure to take into account the year-round temperatures. 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 38°F. Average annual precipitation for Winchester is 50 inches. ### How can I get to and around Winchester? > Mapping out your trip in and around Winchester is easy with these transportation options. Fly into Baltimore Washington Intl. Airport (BWI), which is located 54.5 mi (87.7 km) from the city center. If you'd like to explore around the area, you may want to rent a car for your trip. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [4 Star Hotels in Chesapeake City](https://www.expedia.ca/4Star-Chesapeake-City-Hotels.s40-0-d177517.Travel-Guide-Filter-Hotels) - [Apartments in Arundel](https://www.expedia.ca/Arundel-Apartments.d553248635975849826-aaApartments.Travel-Guide-Accommodation) - [Hotels near Bulle Rock Golf Course](https://www.expedia.ca/Bulle-Rock-Golf-Course-Hotels.0-l6091695-0.Travel-Guide-Filter-Hotels) - [B&B in Charlestown](https://www.expedia.ca/Charlestown-Bed-And-Breakfast.d553248634999088358-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Guest Houses in Charlestown](https://www.expedia.ca/Charlestown-Guest-Houses.d553248634999088358-aaGuestHouses.Travel-Guide-Accommodation) - [Cheap Hotels in Charlestown](https://www.expedia.ca/Charlestown-Hotels-Cheap-Hotels.0-0-d553248634999088358-tCheapHotels.Travel-Guide-Filter-Hotels) - 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