Holiday rentals in Chestertown, Maryland

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Travel insights for holiday rentals in Chestertown

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

What is the cheapest day to stay in a vacation rental in Chestertown?

The cheapest day to stay in Chestertown is Thursday (€131). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is €276.
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Where to stay in Chestertown

Explore different neighbourhoods and areas within Chestertown, MD to find the perfect location for your stay. Map data was last updated on 13 September 2025.
Utilise the map to find properties close to the Chestertown area(s) or attractions you plan on visiting. Clicking on a holiday rental name will take you to a page with pricing, reviews, and more useful information.

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 13 September 2025.

  • How much does a holiday rental in Chestertown cost?

    The average cost for a holiday rental in Chestertown is €235/night. A good holiday rental deal in Chestertown would be for €221/night or less. The cheapest rental deal found recently by our users was €102/night. If you’re flexible with your travel dates, then try to avoid booking April, the most expensive month of the year. Booking March is the cheapest month to book a holiday rental in Chestertown.

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Consider other places to stay in Chestertown

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