Gorgeous home in town center & short walk to WAC - 5-bedroom, verified, house, on Houfy, (sleeps 10), from $299/night, rated 5/5, with 227 reviews

Gorgeous home in town center & short walk to WAC

Stunning 9 Bedroom Villa on the Chesapeake Bay - 9-bedroom, verified, villa, on Houfy, (sleeps 28), from $2,000/night, rated 5/5, with 4 reviews

Stunning 9 Bedroom Villa on the Chesapeake Bay

Waterfront Haven w/EV &Garage - 3-bedroom, verified, house, on Houfy, (sleeps 6), from $260/night, rated 5/5, with 1 review

Waldins Chesapeake - 3-bedroom, verified, house, on Houfy, (sleeps 10), from $399/night, rated 4.93/5, with 54 reviews

Off The Chart Stays - 2-bedroom, verified, cottage, on Houfy, (sleeps 6), from $400/night, rated 5/5, with 8 reviews

The Shellback:  Annapolis, MD - 3-bedroom, verified, house, on Houfy, (sleeps 7), rated 5/5, with 15 reviews

Vacation rentals in Chestertown, Maryland, United States. 6 properties found.