The town of St. Michaels is rich in history, having gained the nickname of “the town that fooled the British” during the War of 1812. Today, St. Michaels has a healthy tourism industry as guests come from far and near to enjoy all the wonderful things this charming community has to offer. There are upscale shops, historical sites and museums, seafood restaurants, boat tours, nearby golf courses, and so much more. Many will also recognize St. Michaels as the backdrop of several popular movies, including “The Wedding Crashers”!

Would you like to experience this gorgeous, historical community for yourself? Eastern Shore Vacation Rentals has you covered! Simply scroll down to explore our variety of St Michaels, MD, vacation rentals, and reserve your favorite!

Browse Our St. Michaels Vacation Rentals Below