Give yourself some wiggle room If your plans are flexible, play around with some different travel dates – a shift of a few days either way can help you save big. Prices usually jump the weekends before and after popular holidays, so we recommend steering clear of them. Or consider visiting during the off-season, when prices are generally lower. Plan around big events Are prices surprisingly high? There might be a huge conference or festival in town. Consider shifting your dates if you can. Of course, if that's why you're going, you'll have to bite the bullet. We'll still work to get you the best rates out there. Noodle over new adventures Set aside time to plan what you want to see, taste and discover. Nothing completes a trip, big or small, like a few new experiences! Check city apps or area websites to find out what's new and what events are happening during your stay. Even during a family reunion, you can detour to that locals-only fish taco stand or under-the-radar music club. Your cousins will be impressed.
Chestertown is located on the Chesapeake Bay in northeastern Maryland, 50 miles northeast of downtown Annapolis. The hotels in Chestertown are located off MD 213. The closest city with additional hotels is 28 miles south in Grasonville. Hotels in or near Chestertown Rates shown below are averages. Click See Rates to see rates for your dates.