St. Michaels Vacation Rentals
St Michaels sits on the neck of a peninsula, curved round an inlet off the beautiful Miles River. The perfect vacation destination for those who like to be close to the water. Known to many as "The Heart & Soul of the Chesapeake Bay", St Michaels is a peaceful and charming town that has maintained its historical and colonial ambiance. Imagine times past as you stroll along streets of red brick sidewalks and historic Victorian homes. Many of the historic buildings are home to local boutiques. Restaurants to please every taste and every visitor are scattered along the highway through town, from pizzas to gourmet dining. The Historic Mill Complex has a winery, brewery and distillery. An industrial hip-chic atmosphere and a great place to visit. View our full collection of spectacular St. Michaels vacation rentals.
The St Michaels Harbor is picturesque. Take a harbour or river cruise, charter a yacht, skipjack, or replica of a 1930’s steam ship. The Chesapeake Bay Maritime Museum is set on 18 acres of waterfront and is one of St Michael’s most popular attractions. The Museum has a boatyard keeping the craft and tradition of wooden boats alive.
Surrounded by nature and water, the outdoor activities are endless. Enjoy kayaking, canoeing, paddle-boarding and sailing. There is excellent fishing and crabbing and seasonal guided hunting trips are available. The St Michaels Nature Trail in town is open to pedestrians and cyclists and runs along the former train route. There are a number of cycling routes around the area and the triangle formed by the towns of Easton, Oxford and St Michaels forms a popular route. At the end of the peninsula lies Tilghman Island, a quaint village nestled between the bay and the Choptank River.