Robert Morris Inn & Sandaway, Oxford, Maryland $$$$
Concierge.com's insider take:
While nearby St. Michaels gets the crowds, this is the place for a good old B&B getaway on the Eastern Shore. The 14-room inn, which dates to 1710 and was the residence of Revolutionary War financier Robert Morris, has a full and fascinating history, as does the village of Oxford, one of Maryland's oldest settlements. An antique print in the inn's sitting room shows Morris and George Washington meeting with Betsy Ross to design the nation's first flag. There's also a thank-you note from author James Michener (he outlined his novel Chesapeake in the tavern room) to innkeepers Ken and Wendy Gibson, who've owned the spot since 1971. Rooms 1, 2, 15, and 17 have river views to go along with canopy beds, floral wallpaper, and uneven floors (the original building is nearly 300 years old). The "newer" 18-room Sandaway (built in 1835), a sister property, is a half-block to the west, with enormous trees shading a broad lawn that spills onto a private beach. There are a few cable TVs in the rooms, but no phones. There is Wi-Fi in the lobby, but it seems an anachronism when you could be walking the brick sidewalks to the town's busy docks and marinas to watch watermen unload the day's catch.
Open April though November.