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Vacation rentals in Chestertown, MD

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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 day to stay in a vacation rental in Chestertown?

The cheapest day to stay in Chestertown is Thursday ($180). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $370.
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Other accommodations in Chestertown

Find the perfect vacation rental for your stay in Chestertown, MD. There are 53 hotels in Chestertown, MD and price data was last updated on September 16, 2025. The average price for a hotel in Chestertown, MD is .
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
0.9 mi from city centre
Free Wi-Fi
Parking
$69
Avg. per night
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Where to stay in Chestertown

Explore different neighborhoods and areas within Chestertown, MD to find the perfect location for your stay. Map data was last updated on September 16, 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 September 16, 2025.

  • How much does a vacation rental in Chestertown cost?

    $280 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 $263 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 April, and the cheapest time to book is March.

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Consider other places to stay in Chestertown

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