Horseshoe Bay, St. Michaels, MD ------ Horseshoe Bay includes a 100-acre private island and offers one of the best waterfront vacation experiences available on the Eastern Shore of Maryland. Sandy beaches, two docks, a boat house and a new swimming pool give you total access to water activities. If it is adventure you crave, hiking, canoeing and kayaking practically guarantee wildlife, bird and butterfly sightings and get you closer to the Eastern Shore than you have ever been. Crabbing, fishing and boating are also at your fingertips right on the property or through our charter service. Have a crab feast, a family-style picnic or relax by the water, but at the end of the day, you will not want to miss the amazing sunsets from the screened-in porch! Contact us today to begin planning your vacation at Horseshoe Bay!