The Eastern Shore Hotels

Outside of Cambridge's singular Hyatt Regency and Ocean City's approximately 10,000 hotel rooms—the great majority of accommodations throughout this region a... Read More

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1. Brampton Bed & Breakfast Inn

25227 Chestertown Rd., Rte. 20 W, Chestertown, Maryland, 21620-3944, United States

On 20 wooded acres between the Chester River and the Chesapeake Bay, about 1 mi south of downtown Chestertown,... Read More

2. Combsberry

4837 Evergreen Rd., Oxford, Maryland, 21654-1450, United States

This 1730 brick manor house, together with the carriage house and the Oxford cottage, is set amid magnolias an... Read More

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3. Great Oak Manor

10568 Cliff Rd., Chestertown, Maryland, 21620-4115, United States

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

4. Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina

100 Heron Blvd., Cambridge, Maryland, 21613-3420, United States

This 370-acre complex is the Eastern Shore's first full-service, year-round resort, and one that takes full ad... Read More

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5. Lighthouse Club Hotel

56th St. at Bay, Ocean City, Maryland, 21842, United States

This elegant boutique hotel is a Chesapeake Bay lighthouse lookalike of quiet luxury, just blocks from the bus... Read More

6. Park Place

2nd and 3rd Sts. at boardwalk, Ocean City, Maryland, 21842-4021, United States

Filling a need for more affordable, family- and child-friendly accommodations, this small, multistory hotel on... Read More

7. The Inn at Osprey Point

20786 Rock Hall Ave., Rock Hall, Maryland, 21661-1405, United States

On 30 lush acres along Swan Creek, this stately Colonial-era building welcomes guests with brick fireplaces an... Read More

8. The Lankford Hotel & Apartments

8th St. at boardwalk, Ocean City, Maryland, 21842-0420, United States

Opened in 1924, the Lankford is still owned by the family of the original owners. Many combinations of rooms i... Read More

9. Victoriana Inn

205 Cherry St., St. Michaels, Maryland, 21663, United States

Adirondack chairs line a sloping expanse of lawn leading to the formal gardens of what was once a Civil War ar... Read More

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