6 years ago we stayed at the Maryland Inn, part of the Historic Inns of Annapolis. It is beautiful. I booked several months in advance through hotels.com and got a very good rate. Before that I stayed at the Comfort Inn way out on Old Mill Bottom Rd. because I booked too late and there wasn't much available. It was a much better experience staying downtown, just leaving the car parked for the entire stay and we loved the Maryland Inn.
When we stayed farther out we parked at the college stadium and took the shuttle bus into the show. There are signs everywhere for show parking.