Chestertown, Maryland Bed and Breakfast Inns - and Surrounding Area

Chestertown is home to 300 years of history, so be ready to experience colonial life on your next bed and breakfast visit! With a mix of history, shopping, arts, and exceptional dining, Chestertown is perfect for families, couples, and business travelers looking for relaxation and convenience. When you arrive at your bed and breakfast, your helpful bed and... » show more breakfast innkeepers will be happy to tell you about Chestertown’s rich history, dating back to colonial times. With rich traditions that go back hundreds of years, bed and breakfast guests are sure to appreciate the past when vacationing in Chestertown. Take a stroll and enjoy the colonial homes near your bed and breakfast, or explore the Saturday Farmers Market. Be sure to explore the shopping of Chestertown, where store fronts are filled with one-of-a-kind items, and fresh flowers line the historical streets. Bed and breakfasts guests can take in some local culture at one of the dozen galleries, studios and shops in Chestertown featuring local, regional and international artists. Ask your bed and breakfast innkeepers to recommend their favorite local eatery, and feast on delicious food, from the Bluebird Tavern to the Village Bakery and Cafe. Your bed and breakfast home away from home in Chestertown is waiting! Discover the perfect bed and breakfast today and begin planning your Chestertown getaway! « show less

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bed and breakfast
  Chestertown, MD Nearby Cities:
bed and breakfastBetterton10.1 mi
bed and breakfastRock Hall10.4 mi
bed and breakfastQueenstown18.7 mi
bed and breakfastHavre de Grace23.1 mi
bed and breakfastChesapeake City23.7 mi
bed and breakfastNorth East27.3 mi
bed and breakfastDover, DE29 mi
bed and breakfastAnnapolis29.1 mi
bed and breakfastBaltimore30.1 mi
bed and breakfastEaston30.6 mi
bed and breakfastElkton30.6 mi
bed and breakfastSt. Michaels30.9 mi
bed and breakfastRoyal Oak34.5 mi
bed and breakfastSherwood36 mi
bed and breakfastOxford37.1 mi
* mileage estimated as the crow flies
bed and breakfast


Chestertown B&B Deals and Specials
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  Chestertown Maryland, Bed and Breakfasts Map it
Brampton B&B Inn - Bed and Breakfast

Brampton B&B Inn

Chestertown, MD


Rooms: 12
With Private Bath: 12
Rates: 179.00- 399.00 USD
The award-winning Brampton Inn is a romantic Bed and Breakfast located on Maryland’s eastern shore. 25 landscaped acres ideal for those seeking a luxurious and private escape. 1/2 mile outside the historic town of Chestertown.

The Inn at Mitchell House - Bed and Breakfast

The Inn at Mitchell House

Chestertown, MD


Rooms: 7
With Private Bath: 7
Rates: 109.00- 239.00 USD
Take a step back in time in this 18th-century manor house in a quiet, rural setting. It is located between Chestertown and Rock Hall. Enjoy gardens, ponds and the Chesapeake Bay, a mere 1/2 mile away. This is nature lovers’ paradise.

Great Oak Manor - Bed and Breakfast

Great Oak Manor

Chestertown, MD


Rooms: 12
With Private Bath: 12
Rates: 169.00- 315.00 USD
Come for a romantic getaway to Great Oak Manor where the only honking comes from the geese, where the closest highway is the duck flyway, and where the only traffic you see from your room are the boaters sailing the water of the Chesapeake Bay Waterfront.



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