I've rented from these guys a couple of times.
Sailboat and Power boat rentals and charters in Annapolis, Maryland - Chesapeake Bay
Nice boats, decent prices. The first time we went out with one of their boats, the mainsail tore in some not-very-high winds. They offered to bend on a new main for us (no questions asked about fault), but two of my three crew were seasick, so we said no thanks. They gave us a half-day back on our day's rental that we used another time.
They also gave a nice briefing about getting out of the South River into the Bay, and provided charts.
I am not affiliated with them in any way. But I would rent from them again in an instant if I didn't have my own boat now.
Good luck and have fun!