Chestertown Maryland Hotels, Motels & Lodging

Check out our list of Chestertown, Maryland hotels, motels and other travel lodging options below. Hotels are listed by their proximity to downtown Chestertown. Click on any hotel from the list below to view information, details, and current rates, and to make reservations online.

Comfort Suites Chestertown

160 Scheeler Rd., Chestertown, MD

Rooms begin at $79.99

1 mile from Chestertown city center.

Holiday Inn Express Hotel & Suites CHESTERTOWN

150 SCHEELER ROAD, Chestertown, MD

Rooms begin at $120.00

1 mile from Chestertown city center.

Hotels Near Chestertown

Chestertown Hotels

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Trails Near Chestertown

Chestertown, Centreville, and Wye Mills, MD Chestertown, MD (Day Trips)
The charming little town of Chestertown is situated on the banks of the peaceful Chester River and exemplifies the easy, country living of Maryland’s Eastern Shore. It is renowned for its waterfront h...
The Eastern Shore: Water, Water, Everywhere Chestertown, MD (Weekend Trips)
Water, water, everywhere—in rivers, streams, marshes, and the mighty Chesapeake itself—defines the ecology and the economy of Maryland’s Eastern Shore of the Chesapeake Bay. The level, lush green lowl...
Hart-Miller Island Campground Breezy Point Beach, MD (Campgrounds)
If you want to feel like a modern day Robinson Crusoe, take a boat to Hart-Miller Island, at the mouth of the Back River in the Chesapeake Bay. OK, it’s not so remote that you’ll feel like that famous...
Tuckahoe State Park Campground Jumptown, MD (Campgrounds)
I think the lake’s 40 acres of flooded forestland is the most unique attraction. While the rest of the lake is open water and allows for great fishing, there’s something about paddling around trees te...
Elk Neck State Park Trails North East, MD (Hiking)
Do it all at Elk Neck State Park in one long day of hiking and biking. If it’s summer, leave time for swimming as well. Head straight away from the parking area on the wide, packed-dirt Blue Trail. Yo...
Elk Neck State Park Campground Buttonwood Beach, MD (Campgrounds)
Situated on a peninsula between the Chesapeake Bay and the Elk River, Elk Neck State Park contains a wealth of beauty (though no elk), encapsulated within a real diversity in topography, including bea...
Tuckahoe Creek Loop, Tuckahoe State Park Denton, MD (Hiking)
Tuckahoe Creek might be the quietest stream valley in Maryland, offering a rich diversity of trees, terrain, creeks and bogs, and passage through the Adkins Arboretum. Follow the path behind the park ...