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Holiday rentals in Chestertown, Maryland

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Travel insights for holiday rentals in Chestertown

Use our HotelsCombined data-powered tips to help you find your next holiday rental in Chestertown.

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

The cheapest day to stay in Chestertown is Monday ($194). On the other hand, travelers can expect to pay the most on Sunday, when the average nightly price is $534.

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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 14 June 2026.
Utilise the map to find properties close to the Chestertown area(s) or attractions you plan on visiting. More information on a given holiday rental can be accessed by clicking the holiday rental's name within the map.

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 14 June 2026.

  • How much does a holiday rental in Chestertown cost?

    $455/night is a typical cost for a holiday rental in Chestertown throughout the year. Rental prices do vary though, and you’ll find that October is the most expensive month to book, and December is the cheapest month to book. HotelsCombined users recently found Chestertown holiday rentals for as low as $194/night. In general, any Chestertown rental for $427 or less is a good deal.

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