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Set beside the historic Chesapeake Bay, St. Michaels, Maryland, is a charming seaside town with a laid-back coastal feel and plenty of history to explore. Stay with Inspirato at Mulberry, an expansive, six-bedroom home steps from Grace Creek with its own private dock. Enjoy ample outdoor space, including a pool, outdoor kitchen, and fire pit. Harriet is a five-bedroom, Cape Cod-style home perched on a creek waterfront, offering a private outdoor pool and quick access to the heart of St. Michaels.
Nestled along its picturesque namesake harbor, St. Michaels offers historic charm—there’s a reason it’s nicknamed the Heart and Soul of Chesapeake Bay. Settlers flocked there from the 17th century on to build ships and grow tobacco. Today, St. Michaels is coastal Americana at its finest, with laid-back days best spent on the water. As you wander St. Michaels’ charming harborfront streets, you’ll feel as if you’ve slipped back to the 18th century, with noteworthy bay vessels and skipjacks dotting the coastline and woodlands extending across the region. It’s also an easy weekend getaway from Washington, D.C., Baltimore, or Philadelphia.