Brick streets, sailboats on the harbor and the Naval Academy at the end of the block. Stay in the heart of America's sailing capital.
Find your stayThings to doHistoric downtown homes, Eastport bungalows and family retreats near the water, managed by The House Kee.
Harbor cruises, history walks and food tours, top-rated and bookable in a few taps.
Experiences are booked through our partner Viator. Prices and availability are set by Viator and may change.
A few things we tell every guest.
Shops, seafood and the harbor are all walkable from downtown. Don't miss the Maryland State House, the oldest state capitol still in legislative use.
Just across the Spa Creek bridge: a laid-back maritime neighborhood with marinas, waterfront restaurants and great sunset views back at downtown.
Walk the Yard on a guided tour from the visitor center. Adults need a government-issued photo ID to get on base.
Every May, families come for USNA graduation and homes book up early. See Commissioning Week homes →
Annapolis lives on the Chesapeake. Take a harbor or lighthouse cruise, rent a kayak on Spa Creek, or sail for the afternoon.
Spring and fall are ideal for walking the town. October brings the big Annapolis boat shows; summer is all about crabs and the water.
We manage vacation and Commissioning Week rentals across Annapolis: pricing, guests, cleaning and care. See what your home could earn.
Annapolis rental managementComplete the form below and one of our local property specialists will contact you with a free analysis of your property's rental potential.
