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Hotels in Chestertown, Maryland

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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 ($255). Conversely, the most expensive month to stay in Chestertown is September ($763).

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

The cheapest day to stay in Chestertown is Tuesday ($349). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $856.
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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 $115 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 27 July 2025
For those on a budget, these are the cheapest hotels available in Chestertown for the selected dates. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
$115
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 27 July 2025.

  • What are the best hotels in Chestertown?

    Chestertown is home to many highly-rated hotels, one of which is Comfort Inn and Suites Chestertown, which has a current rating of 8.0. For other potential stays, consider Brampton 1860 and Carriage House Hideaway In Center of Chestertown, which can also be great places to stay in Chestertown.

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

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

  • How many hotels are there in Chestertown?

    In total, there are 55 hotels to choose from in Chestertown, compared to 16,194 properties in Maryland.

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Consider alternative stays in Chestertown

If you are looking for a specific type of hotel, consider these options for trips to Chestertown
Holiday rentals in Chestertown, Maryland

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