Hotels in Chestertown, Maryland
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Travel insights for hotels in Chestertown
Use our HotelsCombined data-powered tips to help you find your next hotel in Chestertown.
What is the cheapest month to book a hotel in Chestertown?
The cheapest month to book a hotel in Chestertown is January (£50). Conversely, the most expensive month to stay in Chestertown is June (£133).
What is the cheapest day to stay in a hotel in Chestertown?
The cheapest day to stay in Chestertown is Tuesday (£66). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is £140.
Cheapest hotels in Chestertown, MD
Discover affordable stays in Chestertown, MD that provide a quality experience without breaking the bank. Hotels in Chestertown, MD can be found for as low as £51 per night. There is currently one property in Chestertown, MD that can be booked for this price. Driftwood Inn is one of the hotels that can be booked for the lowest price in Chestertown, MD. Price data was last updated on 6 June 2025
At the moment, these hotels offer the lowest nightly rate out of those we've come across in Chestertown. Prices will typically fluctuate depending on the dates selected, star rating of hotel, and hotel location.
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609 Washington Avenue, Chestertown, MD, United States
1.0 mi from city centre
Free Wi-Fi
Parking
£51
Avg. per night
25227 Chestertown Road, Chestertown, MD, United States
1.5 mi from city centre
Free Wi-Fi
Air conditioning
£242
Avg. per night