Top 10 Chestertown Hotel Deals

See all 72 Hotels in Chestertown
Holiday Inn Express Hotel & Suites Chestertown
Holiday Inn Express Hotel & Suites Chestertown

150 Scheeler Road, Chestertown 21620

2.5 out of 5.0
4.4 out of 5 (188 reviews)

Situated in Chestertown, this hotel is 0.6 mi (0.9 km) from Washington College and 10.8 mi (17.4 km) from Crumpton Auction. …

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Brampton Bed and Breakfast Inn
Brampton Bed and Breakfast Inn

25227 Chestertown Rd, Chestertown 21620

3.5 out of 5.0

Situated in Chestertown, this bed & breakfast is 2 mi (3.2 km) from Washington College and 26.1 mi (42.1 km) from Queenstow …

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Best Western Kent Narrows Inn
Best Western Kent Narrows Inn
15.1 km from Chestertown
2.5 out of 5.0
3.4 out of 5 (181 reviews)

Situated in Grasonville, this motel is within 12 mi (20 km) of Queenstown Premium Outlets, Chesapeake Bay Bridge, and Sandy …

C$137
Holiday Inn Express Edgewood-Aberdeen-Bel Air
Holiday Inn Express Edgewood-Aberdeen-Bel Air
19.8 km from Chestertown
2.5 out of 5.0
4.1 out of 5 (103 reviews)

Situated in Edgewood, this hotel is within 12 mi (20 km) of Harford Mall, Ripken Stadium, and Harford Community College. …

C$131
Home2 Suites by Hilton Baltimore/White Marsh
Home2 Suites by Hilton Baltimore/White Marsh
22.9 km from Chestertown
2.5 out of 5.0
4.5 out of 5 (452 reviews)

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 Towso …

C$113
Residence Inn by Marriott Baltimore White Marsh
Residence Inn by Marriott Baltimore White Marsh
24.2 km from Chestertown
3.0 out of 5.0
4.5 out of 5 (145 reviews)

Located in Nottingham, this hotel is 1 mi (1.7 km) from White Marsh Mall and within 9 mi (15 km) of Double Rock Park and Moun …

C$152
Hampton Inn Baltimore/White Marsh
Hampton Inn Baltimore/White Marsh
24.4 km from Chestertown
2.5 out of 5.0
4.3 out of 5 (326 reviews)

Located in Nottingham, this hotel is 0.7 mi (1.1 km) from White Marsh Mall and within 9 mi (15 km) of Double Rock Park and …

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Regal Inn & Suites
Regal Inn & Suites
26 km from Chestertown
2.0 out of 5.0
1.8 out of 5 (170 reviews)

Situated in Rosedale, this motel is within 6 mi (10 km) of Patterson Park, National Aquarium in Baltimore, and Johns Hopkin …

C$81
Village Inn
Village Inn
27.1 km from Chestertown
2.0 out of 5.0
2.6 out of 5 (92 reviews)

Situated in Annapolis, this motel is 2.5 mi (4 km) from Bay Hills Golf Club and within 6 mi (10 km) of U.S. Naval Academy and …

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Best Western Smyrna Inn
Best Western Smyrna Inn
28 km from Chestertown
2.5 out of 5.0
4 out of 5 (179 reviews)

Situated in Smyrna, this hotel is within 12 mi (20 km) of Delaware State University, Dover International Speedway, and …

C$96

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Chestertown Hotel Guide

Arranging time in Eastern Chesapeake Shore and want to stay close to central Chestertown? Chestertown has 4 hotels within a 0.1-kilometre (0.06-mile) distance of its central area.

Stay within walking distance of central Chestertown. Accommodations in the area include Holiday Inn Express Hotel & Suites Chestertown and Quality Suites.

One of the very few cheaper hotel options in Chestertown is the Driftwood Inn.

You could check out the Historic Kent Manor Inn and also the Hilton Garden Inn Kent Island. The Historic Kent Manor Inn is situated 30 kilometres (20 miles) from downtown Chestertown. The Hilton Garden Inn Kent Island, is 30 kilometres (18 miles) away. Some more alternatives worth checking out are the Best Western Kent Narrows Inn and the Holiday Inn Express Annapolis - Kent Island.

50 kilometres (30 miles) to the south of Chestertown is St. Michaels, where you'll find Chesapeake Bay Maritime Museum and St. Michaels Museum. If you'd like to spend a few nights in St. Michaels, check out the Inn at Perry Cabin by Belmond and Five Gables Inn and Spa. 70 kilometres (44 miles) to the south of Chestertown, you may also choose to stay at Cambridge, which is home to the Hyatt Regency Chesapeake Bay and Holiday Inn Express Cambridge. Regardless of whether you're passing through or spending a few nights in Cambridge, make sure you visit the Great Marsh Park and Long Wharf Park.

Before you head home from Eastern Chesapeake Shore, why not make sure you catch some sport. Visit Nationals Park to the southwest of Chestertown. For those who are interested in staying close by, make a reservation in the The Jefferson, Washington, DC or Marriott Marquis Washington, DC.

Situated 50 kilometres (31 miles) away from Chestertown is Baltimore Washington International Thurgood Marshall Airport. Stay nearby at Residence Inn by Marriott Baltimore BWI Airport or BWI Airport Marriott.

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