Book the Annapolis Vacation Rentals By Owner included waterfront condo, cozy cottage and specious homes with many more rental features 2- bedroom, 3- bathroom, dinning table, tv, pet friendly, washing macine. Explore historic downtown, visit the U.S. Naval Academy, or sail along the Chesapeake Bay. With charming shops, fresh seafood restaurants, and lively cultural events, there’s always something to enjoy. Whether you need a cozy waterfront cottage or a spacious family retreat, Annapolis vacation rentals offer comfort and convenience. Book directly with the owner for a seamless stay. Find your ideal rental at Find American Rentals.