Short-Term and Vacation Rentals in Annapolis, MD by iTrip

Annapolis, Maryland, offers short-term and vacation rentals perfect for exploring nearby destinations such as Kent Island, St. Michaels and the Chesapeake Bay. With a location central to the U.S. Naval Academy, visitors enjoy the state capital's parks, beaches, and places of interest like distilleries, vineyards and Thomas Point Shoal Lighthouse. The Annapolis Historic District further enriches the experience. Available properties range from historic homes to waterfront residences, complemented by local amenities like museums, restaurants and bars. For those seeking adventure, activities such as stand-up paddleboarding, kayaking, and canoeing are available. The area is also known for its annual events and festivals, where locals and visitors come together to share good food and music. We encourage you to reserve your vacation rental today and discover the charm and beauty of Annapolis and its community.