There are many places to stay near the heart of Annapolis, as well as at area B&Bs and chain motels a few miles outside town. A unique "Crabtown" option is Boat & Breakfasts, in which you sleep, eat, and cruise on a yacht or schooner; book ahead. During the sailboat and powerboat shows in spring and fall and at Naval Academy commencement in May, hotel reservations are necessary, even a year in advance. Like most places on the water, prices are lower in the cooler months. You can save money on a hotel by booking a room away from the City Dock. To avoid relying on your car (and dealing with the limited parking in the historic area) ask if your hotel has a free shuttle service.
Two reservation services operate in Annapolis.