Lodging in Chestertown, Maryland
Hotels, Lodges, Extended Stay
Comfort Suites 410-810-0555
160 Scheeler Road, Chestertown, MD 21620
Located just one mile from Washington College, the Comfort Suites in Chestertown offers guests an indoor heated pool, high-speed Internet access, meeting rooms and... more info mapHoliday Inn Express Chestertown 410-778-0778
150 Scheeler Road, Chestertown, MD 21620
High-speed wireless Internet, a heated indoor swimming pool and hot tub, fitness center, 24-hour business center, the Express Start breakfast bar, 650 square feet of... more infoImperial Hotel 410-778-5000
208 High Street, Chestertown, MD 21620
The Front Room Restaurant & Bar and 11 deluxe rooms and two suites are available at the Imperial Hotel, convenient to shopping, sightseeing and Washington College. more info map
Bed & Breakfast, Cabins & Cottages
Brampton Bed & Breakfast Inn 410-778-1860
25227 Chestertown Road, Chestertown, MD 21620
A National Register plantation house on Maryland’s Eastern Shore, the award-winning Brampton Bed & Breakfast Inn is a Select Registry lodging establishment that offers... more info mapGreat Oak Manor 410-778-5943
10568 Cliff Road, Chestertown, MD 21620
Styled after an 18th-century English country retreat, the 12,000 square foot, Georgian-style Great Oak Manor features 12 guest rooms decorated in period themes; with... more info mapHill's Inn Bed & Breakfast 410-778-1926
114 Washington Avenue, Chestertown, MD 21620
Located on one and one thirds acres on a historic residential area near the center of town, this three-story American Gothic-style Victorian home has four guest rooms... more info mapInn at Mitchell House, The 410-778-6500
8796 Maryland Parkway, Chestertown, MD 21620
Situated on 12 manicured acres located less than one mile from the Chesapeake Bay, this lovely 18th century manor home features five guest rooms. A one-bedroom,... more info mapLauretum Bed & Breakfast Inn 410-778-3236
954 High Street, Chestertown, MD 21620
Listed in the National Register of Historic Places, Lauretum Bed & Breakfast Inn offers five guest rooms with private baths. A continental plus breakfast buffet is... more info mapRiver Inn at Rolph's Wharf Marina, The 410-778-6389
1008 Rolph's Wharf Road, Chestertown, MD 21620
Six guest accommodations are available. more info mapSimply Bed & Bread 410-778-4359
208 Mount Vernon Avenue, Chestertown, MD 21620
Located 100 Yards from Washington College Campus
This cozy Cape Cod on Maryland's Eastern Shore, near the Chesapeake Bay; Simply Bed & Bread offers two spacious guest rooms. more info mapWhite Swan Tavern 410-778-2300
231 High Street, Chestertown, MD 21620
The restored, pre-Revolutionary War White Swan Tavern is a bed and breakfast that offers six accommodations with full private baths, central heat and air conditioning,... more info mapWidow's Walk Inn Bed & Breakfast 410-778-6455
402 High Street, Chestertown, MD 21620
Located in the Historic District
Situated on Maryland's Upper Eastern Shore, near the Chester River, Washington College, many historic homes and buildings, gift shops and fine restaurants; Widow's Walk... more info mapLodging Guides and Directories-
Lodging in Chestertown
Towns Near Chestertown
