We had a thoroughly lovely time at the Maryland Inn. The staff were warm and helpful, and the history of the building was fascinating. The location was perfect as it was right on Main Street, which is filled with great restaurants, cute shops and book stores. The area is very walkable.
If you do stay in the Maryland Inn, be aware that you actually check in at the Governor Calvert House, which is a couple streets away. If you arrive by car, you go to the Governor Calvert House, where, after you check in, a valet will drive you back to the Maryland Inn and then will park your car. While this process was a little confusing to us at first, the staff made every effort to make this as easy and pleasant as possible. They do allow you to leave your bags with them before and/or after check in and check out, which was really nice for us, as it gave us time to have a meal in Annapolis after checkout and not have to worry about parking or our bags. The heater in the room did cycle on and off, which interrupted my husband's sleep, so again, something to be aware of. But the bed was very comfortable, and everything was clean and very well-cared for. We felt like we were staying somewhere special, and felt very well taken care of!