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Top Chestertown Luxury Hotels

Driftwood Inn

609 Washington Avenue, Chestertown, MD

Free cancellation

Reserve now, pay when you stay

CA $87

per night

May 21 - May 22

Stay at this motel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attraction Rolphs Wharf Marina is located nearby.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

If you’re looking for a luxury vacation in Chestertown, with plush bedding, designer toiletries, world-class concierge staff, and access to the best restaurants and spa treatments, Travelocity has everything you need. You can live it up like the rich and famous in a luxury hotel in Chestertown with discounts and offerings from Travelocity. Now you can have all the luxury perks you want, and stay on the cheap. So live it up! A luxury hotel in Chestertown can whisk you away without breaking the bank.