Hotels in Chestertown

14 hotels in Chestertown, MD — with photos, guest ratings, amenities and booking links. Showing 1–14 of 14, ranked by review volume.

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All places to stay in Chestertown Guesthouses & B&Bs (10)Apartments & Holiday Homes (1)Resorts & Lodges (1)

Brampton 1860, Hotel in Chestertown

Brampton 1860★★★★★

25227 Chestertown Rd, Chestertown, MD 21620

BreakfastPet friendly

Comfort Inn & Suites Chestertown, Hotel in Chestertown

Comfort Inn & Suites Chestertown

150 Scheeler Rd, Chestertown, MD 21620

Driftwood Inn, Motel in Chestertown

Driftwood Inn★★

609 Washington Avenue, Chestertown

Red Roof Inn, Hotel in Chestertown

Red Roof Inn★★★

160 Scheeler Road, Chestertown

White Swan Tavern, Hotel in Chestertown

White Swan Tavern

Comfort Inn & Suites

150 Scheeler Road, Chestertown

Holiday Inn Express & Suites

Inn at Perry’s Cabin, Hotel in Chestertown

Inn at Perry’s Cabin

Dorchester House, Chestertown, MD 21620

Lodging at the Imperial

Red Roof Inn Chestertown

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