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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 ($214). Conversely, the most expensive month to stay in Chestertown is September ($576).

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

The cheapest day to stay in Chestertown is Tuesday ($284). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is $720.
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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 $105 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 11 July 2025
At the moment, these hotels offer the lowest nightly rate out of those we've come across in Chestertown. Consider alternative dates if you're able to compare prices.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
$105
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 11 July 2025.

  • What are the best hotels in Chestertown?

    Comfort Inn and Suites Chestertown (8.0/10 from 234 reviews), Brampton 1860 (9.7/10 from 41 reviews), and Carriage House Hideaway In Center of Chestertown (9.9/10 from 55 reviews) are all highly rated places to stay in Chestertown.

  • How much is a cheap hotel in Chestertown?

    $99 per night is the cheapest Chestertown hotel price found in our data from the last 72 hours. This coming weekend (18 July to 20 July), prices can start from as low as $104/night.

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

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

  • How many hotels are there in Chestertown?

    In total, there are 50 hotels to choose from in Chestertown, compared to 15,858 properties in Maryland.

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Consider alternative stays in Chestertown

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