Travel
Chestertown is a small, charming town with limited accommodations, so we encourage guests to book early. We’ve reserved hotel blocks and listed great Airbnb options below! The nearest airports are listed at the bottom.
Hotel
Osprey Point Inn
20786 Rock Hall Avenue, Rock Hall, MD 21661
Hotel
Haven Harbour Marina
20880 Rock Hall Avenue, Rock Hall, MD 21661
Hotel
Comfort Inn & Suites Chestertown
150 Scheeler Road, Chestertown, MD 21620
Hotel
Inn at Huntingfield Creek and Getaway Cottages
4928 Eastern Neck Road, Rock Hall, MD 21661
House Or Rental
Studio in Historic Chestertown
Chestertown, MD 21620
Sleeps three
House Or Rental
Historic Downtown Garden Oasis
Chestertown, MD 21620
Sleeps two
Hotel
The Portside Manor
Sleeps eight
House Or Rental
Apartment in the heart of Chestertown
Sleeps four
House Or Rental
1900 Home
Sleeps six
House Or Rental
Historic Downtown Home
Sleeps eight
House Or Rental
Cozy Three Bedroom
Sleeps six
House Or Rental
Classic Victorian in Chestertown Center
Sleeps eight
House Or Rental
Historic Loft
Sleeps four
House Or Rental
Historic Home
Sleeps five
House Or Rental
Cozy Carriage House
Sleeps two
House Or Rental
Country Estate
Sleeps ten
House Or Rental
Riverfront Home
Sleeps fourteen
Flight
Baltimore Washington International
BWI is a 1 hour and 15 minute drive from Chestertown
Flight
Ronald Reagan Washington National Airport
DCA is a 1 hour and 30 minute drive from Chestertown
Flight
Dulles International Airport
IAD is a 2 hour drive from Chestertown
Flight
Philadelphia International Airport
PHL is a 1 hour and 15 minute drive from Chestertown
For all the days along the way