iTrip Annapolis manages short-term rentals in Annapolis, Kent Island and St. Michaels in Maryland.
Affectionately known as the “Sailing Capital of the U.S.,” Annapolis is home to the U.S. Naval Academy and historical attractions. Kent Island ranks among the largest islands in Chesapeake Bay and has parks, beaches, distilleries and vineyards. St. Michaels is a pet-friendly community ideal for festivals and weddings, waterfront dining, and spas.
As local short-term rental property managers in Annapolis, we focus on building long-lasting relationships with homeowners, guests, and real estate investors, and offer a
vacation guide to each guest to enhance their stay. Our portfolio of
vacation rentals includes historic homes in downtown, waterfront homes on Chesapeake Bay, and show-stopping estates for the most luxurious stays. To make each stay a five-star experience, we also provide guest gift baskets and welcome pets in many homes.
Interested in earning more from your rental? Learn
about us and our full-service Annapolis rental property management program and meet our team.