Hotels in Chestertown

7 hotels in Chestertown, MD — with photos, guest ratings, amenities and booking links. Showing 1–7 of 7, ranked by review volume.

All places to stay in Chestertown Guesthouses & B&Bs (1)

Brampton 1860, Hotel in Chestertown

Brampton 1860★★★★★

25227 Chestertown Rd, Chestertown, MD 21620

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

Inn at Perry’s Cabin, Hotel in Chestertown

Inn at Perry’s Cabin

Dorchester House, Chestertown, MD 21620

← All places to stay in Chestertown