Pet-Friendly Places to Stay in Chestertown

3 places to stay in Chestertown, MD — ranked by guest rating, with photos, amenities and booking links.

All places to stay in Chestertown Spa (1)EV charging (1)Parking (3)Breakfast included (3)Remote-work friendly (1)

Brampton 1860, Hotel in Chestertown

Brampton 1860★★★★★

25227 Chestertown Rd, Chestertown, MD 21620

BreakfastPet friendly

Red Roof Inn, Hotel in Chestertown

Red Roof Inn★★★

160 Scheeler Road, Chestertown

Driftwood Inn, Motel in Chestertown

Driftwood Inn★★

609 Washington Avenue, Chestertown

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