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  • Brampton Bed and Breakfast Inn

    The Brampton has been welcoming guests since 1987. We have 13 rooms, suites and cottages. The plantation house sits on 20 acres of landscaped gardens, meadows and woods, and is listed on National Register of Historic Places.

    Contact: Danielle Hanscom
    25227 Chestertown Road - Chestertown, MD 21620
    (p) 410-778-1860, (f) , Email

  • Brittland Estates

    Contact: Natalie Turner
    205 Cannon Street - Chestertown, MD 21620
    (p) 443-282-0860, (f) 410-810-1571, Email

  • Colonial Manor Apartments

    54 Unit Apartments – Built 1967. All two bedroom, 1 bath with laundry facility. Wall to wall carpet and central air conditioning. Managed by Lee Davis

    Contact: Lee Davis or Nancy Beck
    100 Hadaway Drive, P.O. Box 630 - Chestertown, MD 21620
    (p) 410-778-3049, (f) 410-778-9381, Email

  • Cottage on Kent

    Cottage on Kent is located within walking distance to downtown, the Chester River and Washington College.  The Cottage is beautifully appointed with antiques.  It has one bedroom with a queen-sized bed, a full kitchen, a spacious bathroom, off-street parking and access to an outside sitting area.

    We welcome you to Chestertown and hope you have a relaxing stay at Cottage on Kent.

    Contact: Dave & Lorraine Slama
    400 N. Kent Street - Chestertown, MD 21620
    (p) 443-480-0658, (f) , Email

  • Great Oak Manor

    Contact: Holly McKee
    10568 Cliff Road - Chestertown, MD 21620
    (p) 410-778-5943, (f) , Email

  • Holiday Inn Express Hotel & Suites

    Contact: Sandeep Thakrar
    150 Scheeler Road - Chestertown, MD 21620
    (p) 410-778-0778, (f) 410-778-6178, Email

  • Inn at Huntingfield Creek, LLC

    Contact: Jim & Joanne Rich
    4928 Eastern Neck Road - Rock Hall, MD 21661
    (p) 410-639-7779, (f) 410-639-2924, Email

  • Kent County Lodging Association

    Contact: c/o Joanne Rich
    4928 Eastern Neck Rd - Rock Hall, MD 21661
    (p) 410-742-9999, (f) 410-639-2924, Email

  • Kent Crossing Apartments

    168 Unit Apartments – Built 1988. One, two and three bedroom apartments. Washer, dryer, stove, refrigerator, microwave, dishwasher, central air condition and wall to wall carpet. Managed by Lee Davis.

    Contact: Lee Davis or Nancy Beck
    101 Morgnec Road - Chestertown, MD 21620
    P.O. Box 630
    (p) 410-778-3049, (f) 410-778-9381, Email

  • Osprey Point Inn, Restaurant & Marina

    Contact: Terry Nelson
    20786 Rock Hall Avenue - Rock Hall, MD 21661
    (p) 410-639-2194, (f) 410-639-7011, Email

  • Simply Bed & Bread

    Lovely guest house conveniently located within walking distance to Washington College and Chester River Hospital Center.

    Contact: Cheryl Hoopes
    208 Mt. Vernon Avenue - Chestertown, MD 21620
    (p) 410-778-4359, (f) 410-778-7594, Email

  • Sunset Lodge

    We are a private estate located on the Chesapeake Bay with a personal beach, offering stunning waterfront views and picturesque sunsets every night. We have weekly rentals and can accommodate events.

    Contact: Meagan Wick
    4480 Eastern Neck Road - Rock Hall, MD 21661
    (p) 410-639-7846, (f) , Email

  • White Swan Tavern, The

    See Chestertown Spy Video: Christian Havemeyer on the Preservation of the White Swan Tavern The White Swan Tavern has been a familiar landmark in Chestertown since pre-Revolutionary War days. Not far from the great Eastern cities of Baltimore, Washington, and Philadelphia, the White Swan Tavern is a quiet, elegant historic inn nestled in the history of Maryland’s Chesapeake Bay region. The White Swan is for those who treasure serene streets, birdsong mornings, impeccable service, and the grace of New World Tradition. Today the tavern operates as a bed and breakfast, offering accommodations and afternoon tea, as well as amenities for small conferences, weddings, and receptions. Just as it was described in the 18th century, the White Swan remains “a comfortable… Public House… with every attention given to render comfort and pleasure to such as favor it with their patronage.”

    Contact: Sarah Crump
    231 High Street - Chestertown, MD 21620
    (p) 410-778-2300, (f) 410-778-4543, Email