Let's start by what's good: location! Historic Inns of Annapolis has three inns in different locations, we stayed at the Maryland Inn, on Main St / Church Circle, and it was great for walking around to the main attractions, shopping, dinning, etc.
What's bad: 1) you check in at the main Inn but if you're not staying there you have to walk, with your luggage, to where you'll be staying, this can be very annoying in general and worse if it's too hot or too cold or raining; 2) the bathrooms are tiny, no counter space, the shower is super small, it wouldn't fit a tall / large person, the water has little pressure, and there's no good position the shower. The bathroom was a real disappointment, and 3) the Inn is a bit rundown, doors got jammed because of the heat, I understand historical, but it would benefit from a few improvements.
Additionally, we were woken up by the fire alarm one night, and after everything was cleared out, no one explained what happened, what caused it, etc. We felt insecure.