Title: Chestertown B&B: Find the Best Bed and Breakfast from CA $305 | Expedia.ca [Hotels in Chestertown](https://expedia.ca/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.ca/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.ca/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Chestertown Car Rentals](https://expedia.ca/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.ca/Chestertown.d7215.Destination-Travel-Guides) ![Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find a Bed and Breakfast in Chestertown from CA $305 - ![](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 28 - Nov 30](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-11-28&endDate=2025-11-30&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two weeks [Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-05&endDate=2025-12-07&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In one month [Dec 19 - Dec 21](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2025-12-19&endDate=2025-12-21&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) In two months [Jan 16 - Jan 18](https://www.expedia.ca/Hotel-Search?regionId=7215&startDate=2026-01-16&endDate=2026-01-18&adults=2&lodging=BED_AND_BREAKFAST&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Browse Select Chestertown B&B ![Lake](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/694681d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/72010305.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/f2afc3df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/8889a53b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at Huntingfield Creek Rock Hall 10/10 Exceptional (56) "We stayed one night for our Anniversary, and the stay was so peaceful. The grounds are beautiful, the staff so nice, and the main house is amazing. We definitely plan on making this an annual thing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Aaron [](https://www.expedia.ca/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.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 (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) ![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) ### Vandiver Inn Havre De Grace 9.4/10 Exceptional (529) "Lovely inn & receptionist was wonderful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Deborah [](https://www.expedia.ca/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110890000/110888200/110888141/375d9e9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110890000/110888200/110888141/d8b85bc3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![TV](https://images.trvl-media.com/lodging/111000000/110890000/110888200/110888141/8780eb6b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110890000/110888200/110888141/ca21a61d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy Smyrna 10/10 Exceptional (1) "Overall great place. Nice neighborhood. Very spacious and clean living area. Loved having the pool table and all the games. Lisa is a great host and the breakfast is delicious. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) David W. CA $211 CA $654 total includes taxes & fees Nov 22 - Nov 23 [](https://www.expedia.ca/Smyrna-Hotels-Charming-Bed-Breakfast-In-Smyrna-With-AC.h110888141.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/cc957ab5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/6c83d519.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/w1857h2500x0y0-ac5cefb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn Historic District 9.4/10 Exceptional (81) "The Inn is beautiful and the staff very welcoming. My room was spotless, cozy, and tastefully decorated. The location is directly across the street from the USNA. I skipped breakfast, but the offerings looked lovely. Will definitely stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elizabeth CA $268 CA $305 total includes taxes & fees Nov 23 - Nov 24 [](https://www.expedia.ca/Annapolis-Hotels-Flag-House-Inn.h27530544.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=2025-12-05&endDate=2025-12-06®ionId=7215&adults=2&lodging=BED_AND_BREAKFAST&sort=RECOMMENDED&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=AA_BF_PROMO_7215) ![](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%2FChestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "." [](https://expedia.ca/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Comfort Inn & Suites Chestertown](https://images.trvl-media.com/lodging/2000000/1710000/1700800/1700736/a1387f46_y.jpg) ### Comfort Inn & Suites Chestertown 10/10 Excellent "The room was a great size and very clean. The staff were very accommodating and friendly. The amenities were very good. We would definitely recommend this hotel. " [](https://expedia.ca/Chestertown-Hotels-Comfort-Inn-Suites.h1700736.Hotel-Information) ![Garner Hotel Glen Burnie BWI Airport Area by IHG](https://images.trvl-media.com/lodging/1000000/30000/21100/21017/70fc99c2_y.jpg) ### Garner Hotel Glen Burnie BWI Airport Area by IHG 10/10 Excellent "The staff was very pleasant, check in was smooth and the room was clean and comfortable." [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-S-Glen-Burnie.h21017.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A](https://images.trvl-media.com/lodging/2000000/1920000/1916100/1916020/f387b1aa_y.jpg) ### La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A 10/10 Excellent "Clean room" [](https://expedia.ca/Edgewood-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Bel-AirI-95-Exit-77A.h1916020.Hotel-Information) ![Americas Best Value Inn Edgewood](https://images.trvl-media.com/lodging/1000000/30000/20100/20063/b1bb9d9d_y.jpg) ### Americas Best Value Inn Edgewood 10/10 Excellent "Staff is amazing & understanding " [](https://expedia.ca/Edgewood-Hotels-Hilltop-Motel.h20063.Hotel-Information) ![La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh](https://images.trvl-media.com/lodging/1000000/10000/3900/3897/8051c714_y.jpg) ### La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh 10/10 Excellent "Very good, clean no evidence of animals , I Am allergic , very decent and affordable. " [](https://expedia.ca/Baltimore-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Baltimore-N-White-Marsh.h3897.Hotel-Information) ![Quality Inn & Suites Bel Air I-95 Exit 77A](https://images.trvl-media.com/lodging/5000000/4870000/4862300/4862298/95fafc76_y.jpg) ### Quality Inn & Suites Bel Air I-95 Exit 77A 10/10 Excellent "Nice room" [](https://expedia.ca/Edgewood-Hotels-Quality-Inn-Suites-Bel-Air-I-95-Exit-77A.h4862298.Hotel-Information) ![Hilton Garden Inn Baltimore/White Marsh](https://images.trvl-media.com/lodging/1000000/440000/433700/433663/09307c3d_y.jpg) ### Hilton Garden Inn Baltimore/White Marsh 10/10 Excellent "Great friendly staff. Security guard even was friendly and greeted us coming and going. Room was clean and good size. " [](https://expedia.ca/Baltimore-Hotels-Hilton-Garden-Inn-BaltimoreWhite-Marsh.h433663.Hotel-Information) ![Hampton Inn Baltimore/Glen Burnie](https://images.trvl-media.com/lodging/1000000/10000/2800/2759/526c2bf4_y.jpg) ### Hampton Inn Baltimore/Glen Burnie 10/10 Excellent "Room was spotless, beds were very comfortable and breakfast was good" [](https://expedia.ca/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ## Find out more about Chestertown ## Chestertown B&B information | Number of reviews | 600 | | --- | --- | | Accommodation | 8 B&B | | Lowest Price | CA $305 | | Highest Price | CA $654 | ## Frequently asked questions ### Searching for B&Bs in Chestertown? > If you're looking for something a little quirkier than your standard hotel experience, a stay at a bed and breakfast might be the perfect option for your trip. While you're enjoying your trip to Chestertown, Chestertown Dog Park and Urieville Park are perfect spots to get in some fresh air and greenery. ### Why choose B&Bs instead of traditional hotels? > Every B&B has a unique charm. Whether it's a picturesque garden or a beautiful dining room, the little details are what make bed and breakfasts a home away from home. ### What are the best B&Bs in Chestertown? > Here are some B&Bs in the area: [Inn at Huntingfield Creek](https://www.expedia.ca/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information): 12 rooms. Situated 11.3 mi (18.2 km) from the heart of Chestertown. Enjoy the local cuisine breakfast and jetted tubs. [Inn at Haven Harbour](https://www.expedia.ca/Rock-Hall-Hotels-Inn-At-Haven-Harbour.h117514499.Hotel-Information): 24 rooms. 11 mi (17.7 km) from the heart of downtown. Enjoy the onsite dining and outdoor pool. ### When should I book my B&B in Chestertown? > When you're planning your stay in Chestertown, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches. ### What is there to do in Chestertown? > When you want to explore some cultural attractions on your trip, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater are worthy sites to check out. You might put Chestertown Historic District and Rolphs Wharf Marina on your list if you want to see more of the area. ### How can I get to and around Chestertown? > You can map out your trip in and around Chestertown ahead of time with these transportation options. Fly into Baltimore, MD (MTN-Martin State), which is located 20.3 mi (32.7 km) from the heart of the city. You can also search for flights into Easton, MD (ESN-Easton - Newnam), which is 28.2 mi (45.3 km) away. 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