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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 Sunday ($221). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $737.

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Other accommodations in Chestertown, MD

Find the perfect holiday rental for your stay in Chestertown, MD. There are 42 hotels in Chestertown, MD and price data was last updated on 12 December 2025. The average price for a hotel in Chestertown, MD is .
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
$104
Avg. per night
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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 12 December 2025.
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 12 December 2025.

  • How much does a holiday rental in Chestertown cost?

    $455 per night is how much a holiday rental in Chestertown costs, on average. $209 per night was the cheapest price recently found by our users, though anything for $427 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 August, and the cheapest time to book is November.

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