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Top Chestertown Hotels Deals

See all 100 Hotels in Chestertown
Holiday Inn Express Hotel & Suites Chestertown

Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown
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.

$87

$87
John L Stam House

John L Stam House

114 Washington Ave, Chestertown
3.5 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.

$190

$190
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown
2.5 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.

$57

$57
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown
4.0 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.

Inn at Mitchell House

Inn at Mitchell House

8796 Maryland Pkwy, Chestertown
3.5 out of 5.0

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

$150

$150
Quality Suites

Quality Suites

160 Scheeler Rd, Chestertown
3.0 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.

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

5625 O'Donnell Street, Baltimore
3.5 out of 5.0

The Best Western Plus is located just off highway I-95 and 3.8 miles (6.1 km) from Baltimore's port and Cruise Terminal. Little Italy’s restaurants, cafés, and ...

$76

$76
The Inn at Chesapeake Bay Beach Club

The Inn at Chesapeake Bay Beach Club

180 Pier One Road, Stevensville
4.5 out of 5.0

Situated in Stevensville, this hotel is within 9 mi (15 km) of Chesapeake Exploration Center, Chesapeake Bay Bridge, and Sandy Point State Park. Chesapeake Bay ...

$149

$149
Home2 Suites by Hilton Baltimore/White Marsh

Home2 Suites by Hilton Baltimore/White Marsh

10465 Philadelphia Road, White Marsh
3.0 out of 5.0

Situated in the entertainment district, this hotel is 2.2 mi (3.6 km) from White Marsh Mall and within 12 mi (20 km) of Towson University and Double Rock Park. ...

$85

$85
Holiday Inn Express Hotel & Suites Dover

Holiday Inn Express Hotel & Suites Dover

1780 N Dupont Hwy, Dover
3.0 out of 5.0

Situated in Dover, this hotel is within 2 mi (3 km) of Dover Commons Shopping Center, Pedestrian Mall, and Dover Mall. Delaware State University and North Dover ...

$93

$93