The Eastern Shore Hotels

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The Eastern Shore Hotels

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Brampton Bed & Breakfast Inn

  • $$$

On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 mi south of downtown Chestertown, this mid-19th-century...


  • $$$

This 1730 brick manor house, together with the carriage house and the Oxford cottage, is set amid magnolias and willows on the banks...

Great Oak Manor

  • $$$

On 12 acres sloping gently to a gazebo on the edge of its private Chesapeake beach, this stately 18th-century Georgian brick manor house...

Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

  • $$$

This 370-acre complex is the Eastern Shore's first full-service, year-round resort, and one that takes full advantage of the soothing...

Lighthouse Club Hotel

  • $$$

This elegant boutique hotel is a Chesapeake Bay lighthouse lookalike of quiet luxury, just blocks from the busy Coastal Highway. Its...

Park Place

  • $$$

Filling a need for more affordable, family- and child-friendly accommodations, this small, multistory hotel on the boardwalk is owned...

The Inn at Osprey Point

  • $$$

On 30 lush acres along Swan Creek, this stately Colonial-era building welcomes guests with brick fireplaces and exposed beams; four-poster,...

The Lankford Hotel & Apartments

  • $$$

Opened in 1924, the Lankford is still owned by the family of the original owners. Many combinations of rooms in the hotel and the adjacent...

Victoriana Inn

  • $$$

Adirondack chairs line a sloping expanse of lawn leading to the formal gardens of what was once a Civil War army officer's home. Set...


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