Where to stay

in Chestertown

Quaint Chestertown awaits: its sports, university life, art, and more!

Venture to sights like Rolphs Wharf Marina and Northern Chesapeake Bay as you discover Chestertown—a city also notable for its college vibe.

Top-rated places to stay near the beach in Chestertown

Best places to stay for families

Comfort Inn & Suites Chestertown is a hotel featuring free parking and free full breakfast that guests like for its helpful staff and clean rooms. You'll be just a short distance from Larrabee Arts Center, located close by. Red Roof Inn & Suites Chestertown is a hotel featuring free parking and laundry facilities that guests like for its helpful staff. You'll be just a short distance from Larrabee Arts Center, located close by.

Recommended hotels

Best places to stay with pools

The Lodge at Great Oak Landing is a lodge featuring a seasonal outdoor pool and a golf course. You'll also be close to Chesapeake Bay and Northern Chesapeake Bay.

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