Nestled on 25 verdant acres in St. Michaels, Maryland—a place known by many as the Hamptons of the Chesapeake—the Inn at Perry Cabin draws in-the-know Washingtonians seeking weekend revelry and relaxed luxury. In this well-heeled maritime community, where historic skipjacks and sailboats share the waters with sleek cabin cruisers, and where the sight of sharp-dressed couples riding on tandem bikes is just as common as those cruising in luxury sports cars, the historic property remains a crown jewel. It was built in 1816 by Purser Samuel Hambleton, the aide-de-camp of Commodore Oliver Hazard Perry; Hambleton designed the space to resemble the Commodore’s cabin on the USS Niagara.

In its nearly 200-year existence, the inn has played many different roles, transforming from a private home to a farm to a riding academy, before finally becoming a hotel. Today the Inn at Perry Cabin is a must-visit destination; luminaries who have stayed here in the past include Margaret Thatcher, Warren Buffett, Sarah Jessica Parker, and Wynton Marsalis. There are 80 guestrooms and suites, some of which feature separate living areas or private decks and verandas; the guestrooms in the Colonial section of the hotel recently underwent a $3 million renovation.

The inn’s gardener, Joanne “Queen of Green” Effinger, lovingly cares for the more than 85 plant varieties that grow in the garden and around the tidal pond, home to birds, crabs, and frogs. The property also boasts a croquet lawn, a bocce court, a private dock, and a swimming pool. The Inn at Perry Cabin, 308 Watkins Lane, St. Michaels, 410-745-2200