St Michaels Vacation Rentals

St. Michaels

Located on Maryland’s Eastern Shore, the colonial and historic town of St. Michaels is a peaceful haven with a charm and ambience that makes it known to many as "The Heart & Soul of the Chesapeake Bay". On the neck of a peninsula, curved round an inlet off the beautiful Miles River with the picturesque St. Michaels Harbor and Pier, this vacation destination is perfect for those who like to be close to the water. Take a harbour or river cruise, or charter a yacht, skipjack, or replica of a 1930’s steam ship. Sportsman can enjoy paddle-boarding, kayaking, excellent fishing and guided hunting. There are a number of cycling routes around the area, in town the St Michaels Nature Trail is open to pedestrians and cyclists and runs along the former train route.

Step back in time

Most of the town’s small streets can be explored by foot on red brick sidewalks and picturesque streets of historic Victorian homes, boutique stores housed in historic buildings and fine art galleries. Step back in time as you stroll the sidewalks and explore the waterfront. Or simply sit, watch the birds, the passing boats and people. You may get to experience one of the historic log canoe races on the Miles River. The most popular tourist attraction is the Chesapeake Bay Maritime Museum set on 18 acres of waterfront. The Museum has a boatyard keeping the craft and tradition of wooden boats alive. Visit the nearby Waterman’s Wharf and lighthouse.

Local Flavor

For a taste of local flavor, the Mill Complex has a winery, brewery and distillery. St. Michaels Winery is located in the historic Sewing Factory Building. The brewery is located in the Old Mill and brewing is done on the premises. The distillery has an industrial hip-chic atmosphere, a fantastic place to visit. Whether it is pizza, a crab house or gourmet dining you are after, St. Michaels caters for every visitor with many restaurants scattered along the main highway through town up to the water’s edge.

Venture a little further to Tilghman Island, located at the end of the peninsula or visit nearby Easton, Cambridge and Oxford, which is just a short ferry ride across the waters.


St Michaels is truly the Heart & Soul of the Chesapeake Bay.