Top 10 Hotels in Chestertown

See all 7 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 (189 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. …

$100
John L Stam House
John L Stam House

114 Washington Ave, Chestertown 21620

3.0 out of 5.0
4.7 out of 5 (7 reviews)

Situated in Chestertown, this bed & breakfast is 0.5 mi (0.8 km) from Washington College and 9 mi (14.5 km) from Crumpton …

$175
Great Oak Manor
Great Oak Manor

10568 Cliff Rd, Chestertown 21620

3.5 out of 5.0
4.5 out of 5 (4 reviews)

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

$156
Inn at Mitchell House
Inn at Mitchell House

8796 Maryland Pkwy, Chestertown 21620

3.0 out of 5.0

Situated near the beach, this bed & breakfast is 11 mi (17.7 km) from Washington College and 21.3 mi (34.3 km) from Crumpto …

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Driftwood Inn
Driftwood Inn

609 Washington Avenue, Chestertown 21620

2.0 out of 5.0
1.8 out of 5 (60 reviews)

Situated in Chestertown, this motel is 0.2 mi (0.4 km) from Washington College and 10.6 mi (17 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 12.3 mi (19.9 km) from Crumpton …

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Quality Suites
Quality Suites

160 Scheeler Rd, Chestertown 21620

2.5 out of 5.0
3.9 out of 5 (104 reviews)

Situated in Chestertown, this hotel is 0.8 mi (1.4 km) from Washington College and 10.8 mi (17.3 km) from Crumpton Auction. …

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Holiday Inn Express Annapolis - Kent Island
Holiday Inn Express Annapolis - Kent Island
9.2 mi from Chestertown
2.5 out of 5.0
4.4 out of 5 (227 reviews)

Situated on a river, this hotel is within 12 mi (20 km) of Queenstown Premium Outlets, Chesapeake Bay Bridge, and Sandy Point …

$113
Hilton Garden Inn Kent Island
Hilton Garden Inn Kent Island
9.4 mi from Chestertown
3.0 out of 5.0
4.5 out of 5 (224 reviews)

Located in the heart of Grasonville, this hotel is within 12 mi (20 km) of Queenstown Premium Outlets, Chesapeake Bay Bridge, …

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The Inn at Chesapeake Bay Beach Club
The Inn at Chesapeake Bay Beach Club
11.5 mi from Chestertown
4.0 out of 5.0
4.7 out of 5 (33 reviews)

Situated in Stevensville, this hotel is within 9 mi (15 km) of Chesapeake Exploration Center, Chesapeake Bay Bridge, and Sand …

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Where to stay in Chestertown

Chestertown Hotel Guide

Are you arranging to spend some time in Eastern Chesapeake Shore? Hoping to book a place to stay in or around Chestertown? You'll find 4 Expedia-listed hotels and apartments located within a 0.1-mile distance of the downtown area.

Looking for accommodation within strolling distance of the center of Chestertown? Holiday Inn Express Hotel & Suites Chestertown and Quality Suites is sure to suit your needs.

Our extensive database contains just a small selection of no-frills lodging options in Chestertown. The Driftwood Inn is one of them.

The Historic Kent Manor Inn is situated 20 miles from the main part of Chestertown. Another option is the Hilton Garden Inn Kent Island, which is situated 18 miles away. Alternatively, check out the rates and amenities at the Best Western Kent Narrows Inn or the Holiday Inn Express Annapolis - Kent Island.

St. Michaels is 30 miles to the south of Chestertown and is home to the Chesapeake Bay Maritime Museum and St. Michaels Museum. St. Michaels hotel options include the Inn at Perry Cabin by Belmond and Five Gables Inn and Spa. Or stay in Cambridge, 45 miles to the south of Chestertown, where you can choose from the Hyatt Regency Chesapeake Bay and Holiday Inn Express Cambridge. The Great Marsh Park and Long Wharf Park are some of the most popular places to check out in Cambridge.

Just because you're traveling, doesn't mean you can't enjoy your love of sport. You'll find Nationals Park 55 miles to the southwest of Chestertown. Those wanting to stay close by can select from the The Jefferson, Washington, DC or the Marriott Marquis Washington, DC.

For those travelers planning on flying via Baltimore Washington International Thurgood Marshall Airport, you might like to book a room at Residence Inn by Marriott Baltimore BWI Airport, or BWI Airport Marriott, which are both a short distance away.