Top 10 Chestertown Hotel Deals

See all 73 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 (192 reviews)

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

C$126
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown 21620

2.0 out of 5.0
1.8 out of 5 (61 reviews)

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

C$82
Inn at Mitchell House

Inn at Mitchell House

8796 Maryland Pkwy, Chestertown 21620

3.0 out of 5.0

Situated near the beach, this inn is 11 mi (17.7 km) from Washington College and 21.3 mi (34.3 km) from Crumpton Auction.

C$199
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 24.1 mi (38.7 km) from Queenstow …

C$251
Great Oak Manor

Great Oak Manor

10568 Cliff Rd, Chestertown 21620

3.5 out of 5.0
4.2 out of 5 (5 reviews)

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

C$320
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 25.4 mi (40.9 km) from Queenstown Premiu …

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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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Comfort Inn & Suites Edgewood - Aberdeen

Comfort Inn & Suites Edgewood - Aberdeen

19.9 km from Chestertown
2.5 out of 5.0
4.1 out of 5 (430 reviews)

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

C$95
Country Inn & Suites By Carlson, Baltimore North, MD

Country Inn & Suites By Carlson, Baltimore North, MD

24.8 km from Chestertown
3.0 out of 5.0
4.1 out of 5 (653 reviews)

Located in Rossville, this hotel is within 9 mi (15 km) of White Marsh Mall, National Aquarium in Baltimore, and Walters Art …

C$119
Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

27.2 km from Chestertown
3.0 out of 5.0
3.6 out of 5 (1,471 reviews)

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. …

C$108

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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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