Title: 20 Best B&B in Chestertown, MD - Bed and Breakfast from $165 | Expedia.com [Chestertown Travel Guide](https://expedia.com/Chestertown.dx7215)[Hotels in Chestertown](https://expedia.com/Chestertown-Hotels.d7215.Travel-Guide-Hotels)[Vacation Rentals in Chestertown](https://expedia.com/Chestertown-Vacation-Rentals.d7215.Travel-Guide-VacationRentals)[Flights to Chestertown](https://expedia.com/Cheap-Flights-To-Chestertown.d7215.Travel-Guide-Flights)[Car Rentals in Chestertown](https://expedia.com/Car-Rentals-In-Chestertown.d7215.Car-Rental-Guide)[Chestertown Vacation Packages](https://expedia.com/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) ![](https://images.trvl-media.com/place/7215/2810851e-b7cc-4dfb-bf7e-dc0611ab1b49.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_bundle_and_save.svg) ### Bundle & Save Get more, spend less whenever you see Bundle & Save deals - ![](https://a.travel-assets.com/travel-assets-manager/pictograms-expedia/light__onekey.svg) ### OneKeyCash Earn OneKeyCash on all your eligible bookings - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light_ftc.svg) ### Upfront pricing We are not like the others - we include taxes and fees ## Check prices for these dates Next weekend [Feb 13 - Feb 15](https://www.expedia.com/Hotel-Search?regionId=7215&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.com/Hotel-Search?regionId=7215&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.com/Hotel-Search?regionId=7215&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.com/Hotel-Search?regionId=7215&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 Chestertown bed & breakfast ![Lake](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/694681d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily local cuisine breakfast](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/1744d173.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Woods Cottage | Living area | Flat-screen TV, fireplace](https://images.trvl-media.com/lodging/16000000/15610000/15600300/15600253/ea9c33ab.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 [](https://www.expedia.com/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) Rock Hall 10/10 Exceptional (59 reviews) "Quiet. Friendly staff. Beautiful grounds. Very clean." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian $156 nightly $173 total Feb 6 - Feb 7 Total with taxes and fees [](https://www.expedia.com/Rock-Hall-Hotels-Inn-At-Huntingfield-Creek.h15600253.Hotel-Information) ![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 (Tydings) | Premium bedding, memory foam beds, desk, iron/ironing board](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/727c3c6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/052f9ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, Private Bathroom (O'Neill) | Living area | Flat-screen TV](https://images.trvl-media.com/lodging/17000000/16210000/16200200/16200162/c3481ecf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Vandiver Inn [](https://www.expedia.com/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) Havre De Grace 9.4/10 Exceptional (535 reviews) "a wonderful place to stay with super friendly staff. easy walks to downtown and restaurants. stayed here before and definitely will be back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Dieter $147 nightly $165 total Feb 16 - Feb 17 Total with taxes and fees [](https://www.expedia.com/Havre-De-Grace-Hotels-Vandiver-Inn.h16200162.Hotel-Information) ![Interior](https://images.trvl-media.com/lodging/111000000/110890000/110888200/110888141/ca21a61d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/111000000/110890000/110888200/110888141/375d9e9f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, WiFi, bed sheets](https://images.trvl-media.com/lodging/111000000/110890000/110888200/110888141/09579ece.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) ### Charming bed & breakfast in Smyrna with AC, WiFi. Enjoy [](https://www.expedia.com/Smyrna-Hotels-Charming-Bed-Breakfast-In-Smyrna-With-AC.h110888141.Hotel-Information) Smyrna 10/10 Exceptional (1 review) "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. $457 nightly $469 total Feb 7 - Feb 8 Total with taxes and fees [](https://www.expedia.com/Smyrna-Hotels-Charming-Bed-Breakfast-In-Smyrna-With-AC.h110888141.Hotel-Information) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/76e5fee9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Chesapeake Suite | Frette Italian sheets, premium bedding, memory foam beds, free minibar](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/49daa5e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/ab8d2ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/28000000/27540000/27530600/27530544/e818c666.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Flag House Inn [](https://www.expedia.com/Annapolis-Hotels-Flag-House-Inn.h27530544.Hotel-Information) Historic District 9.4/10 Exceptional (86 reviews) "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 $182 nightly $207 total Feb 9 - Feb 10 Total with taxes and fees [](https://www.expedia.com/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.com/Hotel-Search?startDate=2026-02-19&endDate=2026-02-20®ionId=7215&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.com/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.com/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FChestertown-Bed-And-Breakfast.d7215-aaBedAndBreakfast.Travel-Guide-Accommodation) ## Top Chestertown Hotel Reviews ![Hampton Inn Baltimore Bayview Campus](https://images.trvl-media.com/lodging/24000000/23840000/23830900/23830804/e92cee9e_y.jpg) ### Hampton Inn Baltimore Bayview Campus 10/10 Excellent "Yes room was great" [](https://expedia.com/Baltimore-Hotels-Hampton-Inn-Baltimore-Bayview-Campus.h23830804.Hotel-Information) ![Home2 Suites by Hilton Baltimore/White Marsh](https://images.trvl-media.com/lodging/6000000/6000000/5992000/5991951/e611db61_y.jpg) ### Home2 Suites by Hilton Baltimore/White Marsh 10/10 Excellent "The room layout was very good. Like it was done by someone who actually traveled a lot. Nice small kitchen. Lots of counter space. Several hooks in bathroom. Counter space in bathroom. " [](https://expedia.com/Baltimore-Hotels-Home2-Suites-By-Hilton-BaltimoreWhite-Marsh.h5991951.Hotel-Information) ![Historic Inns of Annapolis](https://images.trvl-media.com/lodging/1000000/50000/42100/42068/bf4c0cc1_y.jpg) ### Historic Inns of Annapolis 10/10 Excellent "Everything about this beautiful historic hotel was beautiful and perfect—I can’t wait to come back!" [](https://expedia.com/Annapolis-Hotels-Historic-Inns-Of-Annapolis.h42068.Hotel-Information) ![Hyatt Place Kent Narrows & Marina](https://images.trvl-media.com/lodging/78000000/77980000/77974900/77974873/35e0cb86_y.jpg) ### Hyatt Place Kent Narrows & Marina 10/10 Excellent "Room was nice, quiet, clean. Great for a stay-cation on the wateefront" [](https://expedia.com/Grasonville-Hotels-Hyatt-Place-Kent-Narrows-Marina.h77974873.Hotel-Information) ![Pendry Baltimore](https://images.trvl-media.com/lodging/18000000/17400000/17395900/17395897/45fde7f6_y.jpg) ### Pendry Baltimore 10/10 Excellent "My favorite baltimore hotel hands down!" [](https://expedia.com/Baltimore-Hotels-Pendry-Baltimore.h17395897.Hotel-Information) ![Hampton Inn & Suites Edgewood/Aberdeen-South](https://images.trvl-media.com/lodging/5000000/4620000/4617900/4617887/264f48e5_y.jpg) ### Hampton Inn & Suites Edgewood/Aberdeen-South 10/10 Excellent "Room was very nice and clean. Spacious " [](https://expedia.com/Edgewood-Hotels-Hampton-Inn-Suites-EdgewoodAberdeen-South.h4617887.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 "Everything was excellent and will stay with Hampton Inn in the future !" [](https://expedia.com/Baltimore-Hotels-Hampton-Inn-BaltimoreGlen-Burnie.h2759.Hotel-Information) ![Best Western Plus Hotel & Conference Center](https://images.trvl-media.com/lodging/1000000/20000/10300/10260/314defe9_y.jpg) ### Best Western Plus Hotel & Conference Center 10/10 Excellent "Amazing stay. 5 stars! " [](https://expedia.com/Baltimore-Hotels-Best-Western-Plus-Hotel-Conference-Center.h10260.Hotel-Information) ![Courtyard by Marriott Baltimore Downtown/McHenry Row](https://images.trvl-media.com/lodging/43000000/42120000/42119100/42119031/fba8c798_y.jpg) ### Courtyard by Marriott Baltimore Downtown/McHenry Row 10/10 Excellent "The hotel staff are amazing friendly . During snow storm they were still friendly among all The chaos. Recommend " [](https://expedia.com/Holabird-Industrial-Park-Hotels-Courtyard-By-Marriott-Baltimore-DowntownMcHenry-Row.h42119031.Hotel-Information) ## Find out more about Chestertown ## Chestertown B&B information | Number of reviews | 615 | | ----------------- | ----- | | Accommodation | 8 B&B | | Lowest Price | $165 | | Highest Price | $469 | ## Frequently asked questions ### What is the nightly rate for a Bed & Breakfast in Chestertown? ### When is the best time to book a Bed and Breakfast in Chestertown? > As the warm weather settles in, Chestertown comes alive with activities such as the annual Chestertown Tea Party Festival in May, which showcases the town's rich history and lively atmosphere. This event draws visitors eager to participate in parades, craft fairs, and live music, all set against the beautiful backdrop of the Chester River. > > > For those considering a budget-friendly visit, October emerges as an excellent alternative. During this month, the crowds thin out, yet the scenery remains stunning as the fall foliage transforms the landscape into a canvas of vibrant colors. It's a fantastic time to explore the area's historic sites and enjoy the peaceful ambiance without the hustle and bustle of peak tourist activity. ### What is the difference between a Chestertown Bed & Breakfast and a hotel? ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rentals - [Hotels near Washington College ](https://www.expedia.com/Washington-College-Hotels.0-l553248621561000403-0.Travel-Guide-Filter-Hotels) - [Hotels near River Arts Chestertown ](https://www.expedia.com/River-Arts-Chestertown-Hotels.0-l553248621532662298-0.Travel-Guide-Filter-Hotels) - [Hotels near Historical Society of Kent County Maryland ](https://www.expedia.com/Historical-Society-Of-Kent-County-Maryland-Hotels.0-l553248621561000400-0.Travel-Guide-Filter-Hotels) - [Hotels near Garfield Center for the Arts at the Prince Theater ](https://www.expedia.com/Garfield-Center-For-The-Arts-At-The-Prince-Theater-Hotels.0-l553248621561000401-0.Travel-Guide-Filter-Hotels) - [Hotels near Wilmer Park ](https://www.expedia.com/Wilmer-Park-Hotels.0-l553248621561000402-0.Travel-Guide-Filter-Hotels) - 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