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Chestertown Vacation Packages

Welcome! Admire the coastal plains, wetlands and rolling hills around Chestertown in Eastern Maryland, the United States of America.

Chestertown is located approximately 55 miles (89 kilometers) from Washington, the capital of the United States of America, and about 30 miles (48 kilometers) from Baltimore.

No two towns are ever the same; each possesses its own unique qualities. So, hit the road and visit a few of the other areas around Chestertown. Some interesting places within a relatively short distance of Chestertown are Grasonville, 20 miles (32 kilometers) to the north, and Belcamp, 20 miles (32 kilometers) to the southeast.

Grab some transportation and spend some time in Annapolis, a retail and transport hub for the region, located about 30 miles (48 kilometers) away from Chestertown. The place has a number of tourist attractions, including U. S. Naval Academy, Maryland State House and Maryland Quiet Waters Park. If your itinerary allows be sure to visit Ballet Theater of Maryland, St. John's College and Navy-Marine Corps Memorial Stadium before heading back to Chestertown.

The wider region offer some fun outdoor options for those with an affinity for watersports. Swimming and sea kayaking are just two of the popular water-based activities here.

The handiest major airport, Baltimore Washington International Thurgood Marshall Airport, is located in Baltimore, 30 miles (48 kilometers) to the west of Chestertown, which is handy to remember when planning your trip.


Top Hotel Deals

See all 92 Hotels in Chestertown
£70
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown
4.3
of 5, from 48 reviews
2.5 out of 5.0

Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 25.2 mi (40.5 km) from Queenstown Premium Outlets.

Quality Suites

Quality Suites

160 Scheeler Rd, Chestertown
3.9
of 5, from 20 reviews
2.5 out of 5.0

Situated in Chestertown, this hotel is 0.8 mi (1.4 km) from Washington College and 25.4 mi (40.9 km) from Queenstown Premium Outlets.

£43
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown
1.8
of 5, from 30 reviews
2.0 out of 5.0

Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 26.7 mi (42.9 km) from Queenstown Premium Outlets.

£141
John L Stam House

John L Stam House

114 Washington Ave, Chestertown
4.8
of 5, from 5 reviews
3.0 out of 5.0

Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 24.1 mi (38.7 km) from Queenstown Premium Outlets.

Quit Guest Room to Stay in a Country Family Home

Quit Guest Room to Stay in a Country Family Home

7561 Sunburst Ave, Chestertown
0.0 out of 5.0

Situated in Chestertown, this bed & breakfast is 2.7 mi (4.4 km) from Washington College and 26 mi (41.9 km) from Queenstown Premium Outlets.

£115
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown
5.0
of 5, from 1 reviews
3.5 out of 5.0

Nestled on the beach, this Chestertown bed & breakfast is next to a golf course and 9.1 mi (14.6 km) from Washington College.

£112
Inn at Mitchell House

Inn at Mitchell House

8796 Maryland Pkwy, Chestertown
3.0 out of 5.0

Situated near the beach, this bed & breakfast is 11 mi (17.7 km) from Washington College.

Chester River Waterfront, Magnificent Views, Dock, Beach

Chester River Waterfront, Magnificent Views, Dock, Beach

26761 Mallard Rd, Chestertown
0.0 out of 5.0

Situated in Chestertown, this historic vacation home is 2.9 mi (4.7 km) from Washington College and 27.5 mi (44.3 km) from Queenstown Premium Outlets.

Top Deals on Flights

These prices were available within the past 7 days. Prices quoted are per person, return, for the period specified. Prices and availability are subject to change. Additional terms apply.