Title: Winchester B&B: Find the Best Bed and Breakfast from CA $270 | 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 $270 - ![](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 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 weeks [Nov 14 - Nov 16](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-11-14&endDate=2025-11-16&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Nov 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=553248635975872164&startDate=2025-12-26&endDate=2025-12-28&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) ![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) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15090000/15082800/15082750/496ae4cd.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 area was great. People were very friendly and helpful. B&B room was very small, tv wouldn’t work and the bathroom didn’t have cold water running from the sink. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $254 CA $270 total includes taxes & fees Nov 9 - Nov 10 [](https://www.expedia.ca/Chesapeake-City-Hotels-Inn-At-The-Canal-Bed-Breakfast.h15082750.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 Fanny Wallow Room](https://images.trvl-media.com/lodging/33000000/32130000/32128100/32128064/cd5dcb23.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) "Very nice grounds. Super close to Longwood Gardens. Great food by a real chef." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David CA $334 CA $371 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Exton-Hotels-The-Inn-At-Whitewing-Farm.h32128064.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) ![Exterior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/5bf9cecc.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) ![Interior detail](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/a5510d88.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vandiver Inn Havre De Grace 9.4/10 Exceptional (527) "Wonderful stay. Will stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lisa [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.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) ![Exterior](https://images.trvl-media.com/lodging/4000000/3180000/3173700/3173628/092c86af.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) ![Carriage house 1](https://images.trvl-media.com/lodging/4000000/3180000/3173700/3173628/ef63050c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairville Inn Chadds Ford 8.2/10 Very good (479) "Nice quiet place. My suite was beautiful. Breakfast was delicious every morning. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Robert CA $364 CA $405 total includes taxes & fees Dec 3 - Dec 4 [](https://www.expedia.ca/Exton-Hotels-Fairville-Inn.h3173628.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) ![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) ![View from property](https://images.trvl-media.com/lodging/2000000/1160000/1153700/1153614/66f96cf7.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 (180) "This historic B&B provided a quiet retreat and was a welcome change from commercial hotel stays. The innkeeper was very thoughtful and hospitable, which helped to ensure a comfortable stay. I would return!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anonymous traveller [](https://www.expedia.ca/Elkton-Hotels-Elk-Forge-BB-Inn-Day-Spa.h1153614.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=2025-11-16&endDate=2025-11-17®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 ![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 "Yes" [](https://expedia.ca/Wilmington-Hotels-Comfort-Inn-Suites-Newark-Wilmington.h11904.Hotel-Information) ![Sheraton Suites Wilmington Downtown](//images.trvl-media.com/lodging/1000000/10000/4700/4693/72ec9ef5_y.jpg) ### Sheraton Suites Wilmington Downtown 10/10 Excellent "Great stay for an evening out." [](https://expedia.ca/Wilmington-Hotels-Sheraton-Suites-Wilmington-Downtown.h4693.Hotel-Information) ![Red Roof Inn PLUS+ Wilmington - Newark](//images.trvl-media.com/lodging/1000000/10000/7900/7845/aa58fe8d_y.jpg) ### Red Roof Inn PLUS+ Wilmington - Newark 10/10 Excellent "Clean room " [](https://expedia.ca/Wilmington-Hotels-Red-Roof-Inn-PLUS-Wilmington-Newark.h7845.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 "This " [](https://expedia.ca/Wilmington-Hotels-Baymont-By-Wyndham-Newark-At-University-Of-Delaware.h41973.Hotel-Information) ![Sonesta ES Suites Wilmington - Newark](//images.trvl-media.com/lodging/1000000/20000/19100/19062/98de1f1c_y.jpg) ### Sonesta ES Suites Wilmington - Newark 10/10 Excellent "Good" [](https://expedia.ca/Wilmington-Hotels-Sonesta-ES-Suites-Wilmington-Newark.h19062.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 "The staff were friendly and helpful. Rooms were clean and comfortable but there were crickets in the bathroom. Not sure how they were coming in but every time I killed one another one showed up (all weekend)." [](https://expedia.ca/Wilmington-Hotels-Sonesta-Select-Newark.h2091.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 "A lot of nice toppings for the oatmeal. Hostess (Karen) was excellent." [](https://expedia.ca/Wilmington-Hotels-Hyatt-Place-Wilmington-Riverfront.h34927626.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 "The parking lot was safe. There was a lot of lighting." [](https://expedia.ca/Perryville-Hotels-Red-Roof-Inn-Perryville.h11260.Hotel-Information) ![Four Points by Sheraton Newark Christiana Wilmington](//images.trvl-media.com/lodging/1000000/50000/42300/42232/4231dc87_y.jpg) ### Four Points by Sheraton Newark Christiana Wilmington 10/10 Excellent "Nice" [](https://expedia.ca/Wilmington-Hotels-Four-Points-By-Sheraton-Newark-Christiana-Wilmington.h42232.Hotel-Information) ## Find out more about Winchester ## Winchester B&B information | Number of reviews | 923 | | --- | --- | | Accommodation | 6 B&B | | Lowest Price | CA $270 | | 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: [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 heart of Winchester. Enjoy the free cooked breakfast and fireplace in the lobby. [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 downtown core. 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. Situated 17.8 mi (28.7 km) from the heart of Winchester. 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. 10.4 mi (16.7 km) from the heart of downtown. Enjoy the free full breakfast and library. [Fairville Inn](https://www.expedia.ca/Exton-Hotels-Fairville-Inn.h3173628.Hotel-Information): 15 rooms. Located 17.5 mi (28.1 km) from the core of Winchester. Enjoy the free full breakfast and massage services. ### 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. 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