While Southern Maryland has its charms, there are a limited number of hotels in the area. Some nearby options are listed below. For higher-end accommodations, Annapolis, D.C., and Alexandria are each an hour away.
Main town in the area with a bunch of restaurants and a Beach + Boardwalk. If you're around on Friday night, the farmer's market features food trucks, arts and crafts vendors, and local beer/wine offerings.
https://www.northbeachmd.org/friday-night-farmers-market-classic-car-cruise
Worth a trip for the soft serve ice cream. Also sells produce and other farm stand fare. But really, the ice cream.
https://marylandsbest.maryland.gov/producer/spider-hall-farm/
Some people have had great success hunting for fossils here, though not us personally. Still nice for a moderate hike leading to beach access if you're feeling outdoorsy. Protip: the red trail (non-paved) is better and easier than the paved path. https://dnr.maryland.gov/publiclands/Pages/southern/calvertcliffs.aspx
Two sister restaurants in the area, either will hit the spot if you're craving Mexican food or a margarita. Plaza Mexico in North Beach sometimes gets busy during peak weekend hours. http://www.mexicorestaurant.net/
and https://www.plazamexicomaryland.com/
Fast casual sandwich shop in Dunkirk (specifically Dunkirk location) and easy pitstop on the way down to Southern Maryland from the north. We love the roast beef panini; the jam makes it. http://eatchesapeake.com/dunkirk
Can't be on the Chesapeake Bay without mentioning crabs. We tend to catch or buy local and steam them ourselves when we're in Southern Maryland, but as that's likely not feasible for our guests, Jerry's is a well-reviewed seafood option. https://jerrys-place.com/