Great Oak Manor
10568 Cliff Road, Chestertown, MD
Serene and picturesque Georgian mansion with private beach on Chesapeake Bay.
T: +1 410 778-5943. 11 rooms. US$ 165-
www.greatoakmd.com
100 Small Romantic
Hotels & Places
Come discover 100 of the most romantic small hotels and places in the world.
100 Hotel Search » Maryland
Romantic Places in Maryland
Chesapeake Bay’s Eastern Shore
Waterfront villages, antiques, crab cakes and a colonial heritage. Romantic places with colonial ties and water views.
White Swan Tavern
231 High St., Chestertown, MD
Step back into history here at this restored late 18th century tavern inn.
T: +1 410 778-2300. US$ 125-
www.whiteswantavern.com
Brampton Inn
25227 Chestertown Road, Chestertown, MD
Elegant 1860’s National Register house located on 35 acres with glorious views.
T: +1 410 778-1860. 13 room b&b. US$ 220-
www.bramptoninn.com
The Inn at Perry Cabin
308 Watkins Lane St., Michaels, MD
An early l9th century white colonial mansion set on Miles River, a tributary to Chesapeake Bay.
T: +1 410 745 2200. 41 rooms. US$ 245-
www.innatperrycabin.com