Put together a vacation that features just one or two or more. Then consider making an 800-mile circle drive along both shores of the bay and do them all. If you're flying into Chesapeake Country, the most convenient major airport is Baltimore-Washington International, well served by Southwest Airlines. You will need a car. The Chesapeake beckons travelers year-around.
Winter is best for bird watching, when migrating geese, ducks, and swans arrive from the north.
And it's definitely the least-expensive season, although snow is an occasional threat. Midweek tends to be cheaper any season. As an example of winter savings, we made a special trip around the bay in February to find good budget lodgings. Since we were there as a sightseer keen on walking the well-preserved bayside battlefield, a nippy sea breeze didn't bother us a bit. The rate doubles in the summer when the beach tempts.