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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 ($210). On the other hand, travelers can expect to pay the most on Saturday, when the average nightly price is $373.

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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 3 August 2026.
Utilise the map to find properties close to the Chestertown area(s) or attractions you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular holiday rental.

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 3 August 2026.

  • How much does a holiday rental in Chestertown cost?

    $334 per night is how much a holiday rental in Chestertown costs, on average. $176 per night was the cheapest price recently found by our users, though anything for $327 per night or less is a good deal. Keep in mind that Chestertown holiday rental prices fluctuate throughout the year: the most expensive month to book is October, and the cheapest time to book is April.

  • Are there any Bed & breakfast holiday rentals in Chestertown?

    If you’re looking to book a Bed & breakfast holiday rental in Chestertown, then you have 5 to choose from. We recommend looking at Brampton Bed And Breakfast Inn as it’s currently the most popular Bed & breakfast rental among our users.

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