I've never been to Annapolis and I'm a little overwhelmed by all the hotel options. I'd like to stay in a hotel that is central and gives me good sense of what Annapolis is like. I'd love to know where locals tell their friends to stay when they visit, and why those areas and hotels are special. thanks!
If you want to stay in the heart of downtown Annapolis, you can't beat the Annapolis Waterfront Hotel, Autograph Collection. Though pricey, it provides the best location to see all that downtown Annapolis and neighboring Eastport has to offer by foot. You can easily walk through the visitor's entrance at Gate 1 of the Naval Academy from here as well. If you go further "uptown" (Annapolis isn't huge, so this isn't too much of a stretch), you can typically find decent deals at the Loews Annapolis Hotel, the O'Callaghan Annapolis Hotel or the The Westin Annapolis. You may wind up taking a cab at some point, but you could still explore Annapolis by foot from these locations. There are a number of smaller B&Bs downtown, but these four hotels are the major ones to consider if you want to stay where the action is. Enjoy!
Mentioned in this answer: