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Hotels in Chestertown, MD

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Travel insights for hotels in Chestertown

Use these up-to-date, data-driven insights about booking a hotel in Chestertown including ideal times to book, pricing trends, and more.

What is the cheapest month to book a hotel in Chestertown?

The cheapest month to book a hotel in Chestertown is January (C$ 127). Conversely, the most expensive month to stay in Chestertown is December (C$ 361).

What is the cheapest day to stay in a hotel in Chestertown?

The cheapest day to stay in Chestertown is Sunday (C$ 163). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 430.

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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 C$ 95 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 12 December 2025
Out of the hotels in Chestertown we've come across, these properties are priced the lowest. Prices can differ depending on the dates selected, so use the search form to browse more options if you have flexibility.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
C$ 95
Avg. per night
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Facts about staying in Chestertown, MD

Find useful tips and insights about staying in Chestertown to help you make the most of your experience. FAQs were last updated on 12 December 2025.

  • What are the best hotels in Chestertown?

    258 reviews rated Comfort Inn and Suites Chestertown with an average score of 8.0/10. It may also be worth looking into the Brampton 1860, which received a rating of 9.7/10 from 42 reviews. First Floor Studio Apartment in Historic Chestertown could also be a good option, with a score of 9.5/10 from 87 reviews.

  • How much is a cheap hotel in Chestertown?

    C$ 94/night is the cheapest price found for a hotel in Chestertown by HotelsCombined users over the last 72 hours.

  • What are some other cities to stay in when visiting Maryland?

    In addition to Chestertown, travellers opt to visit Baltimore when visiting Maryland. Edgewood is also a popular choice to visit.

  • How many hotels are there in Chestertown?

    In total, there are 42 hotels to choose from in Chestertown, compared to 11,370 properties in Maryland.

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