I suspect that someone will contradict this, but I've never had a problem entering Ocean City inlet at slack tide. Same holds true with Chincoteague Inlet. While Ocean City's back bays are fraught with shoals, they are well marked. The biggest problem you'll encounter with Both Ocean City and Chincoteague the currents exceed most sailing vessel engine capabilities, which is a real problem when you're approaching bridges and the current is ripping at 7 to 8 knots beneath the bridge.
In Ocean City there is really no place that you can safely anchor, but there are lots of places just inside Chincoteague Inlet where depths to 7 feet permit some protection during bad weather.
A bit farther south, you'll find Wachapreague Inlet, which can be a bit tricky during low and ebb tide, but at slack tide it's a piece of cake. Once inside, there are a few spots where you can duck out of the weather or spend the night in relative seclusion, but you better have good screening and no air leaks to the outside. The skeeters down here can stand flat footed and make love to a tom turkey. They'll get you day and night and they WILL draw lots of blood.
Great Machapongo Inlet is a narrow, deepwater inlet that is greatly effected by tidal currents. Keep in mind the tidal change behind Virginia's barrier islands is incredible, often exceeding 10 feet. That's a huge volume of water flowing through a narrow inlet during a tidal change. The inlet is relatively wide, but the channel leading to the back country and Willis Wharf is narrow and deep--it's a slack tide deal only.
Sand Shoal Inlet is a bit tricky, mainly because there are some brand-new islands forming just outside the inlet that cannot be seen at high tide. The approach channel is relatively close to shore, but it's quite deep. Once inside the inlet, there are loads of places to anchor and the depths vary from 2 to 50 feet within a few feet of shore. Lots of protected areas, though. The adjacent tidal marsh is a massive colony of greenhead flies, black flies, mosquitoes, gnats, and other biting, stinging insects. Skin So Soft seems to work best on the flies, while Deet will keep the skeeters at bay.
There are no navigable inlets south of Sand Shoal Inlet until you reach the west side of Fisherman's Island and the mouth of Chesapeake Bay. Granted, there is a great channel that runs from Sand Shoal Inlet south to the east side of Fisherman's Island, but at the end of the channel there is a fixed, 40-foot vertical clearance bridge that only has 4 feet of water beneath it, thus it's out of the question for most sailing vessels.
As you can see, there are a fair number of places where you can duck out of the weather, or spend the night in the stretch of ocean between Ocean City and the mouth of Chesapeake Bay. However, they are only navigable during periods of slack tide. It's just a matter of timing.
Almost forgot: There are lots of large charter and commercial fishing vessels, as well as motor-yachts that can create problems at Ocean City and Chincoteague inlets, especially on busy, summer weekends. They don't give a tinkers damned whether or not you need a little extra space to safely negotiate the inlets and they'll hit you with a 4 to 5-foot wake and damned near run over you as they transit the inlets. On weekdays, the traffic is relatively light, especially between 10 a.m. and noon, when the crazies on jet skis are still sleeping off the previous nights booze and the charter and fishing fleets have long since left the docks and are offshore.
Good Luck,
Gary