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Vacation rentals in Chestertown, MD

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Chestertown, United States
Apr 24 — Apr 252
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Travel insights for vacation rentals in Chestertown

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

What is the cheapest month to book a vacation rental in Chestertown?

The cheapest month to book a vacation rental in Chestertown is February ($158). Conversely, the most expensive month to stay in Chestertown is January ($754).

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

The cheapest day to stay in Chestertown is Tuesday ($137). On the other hand, travelers can expect to pay the most on Monday, when the average nightly price is $499.
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Where to stay in Chestertown, MD

Explore different neighborhoods and areas within Chestertown to find the perfect location for your stay. Map data was last updated on April 17, 2025.
Utilize the map to find properties close to the Chestertown area(s) or attractions you plan on visiting. Clicking on a vacation 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 April 17, 2025.

  • How much does a vacation rental in Chestertown cost?

    $320 per night is how much a vacation rental in Chestertown costs, on average. $120 per night was the cheapest price recently found by our users, though anything for $300 per night or less is a good deal. Keep in mind that Chestertown vacation rental prices fluctuate throughout the year: the most expensive month to book is October, and the cheapest time to book is March.

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