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Vacation rentals in Chestertown, MD

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Other accommodations in Chestertown, MD

Find the perfect vacation rental for your stay in Chestertown, MD. There are 43 hotels in Chestertown, MD and price data was last updated on June 12, 2025. The average price for a hotel in Chestertown, MD is .
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Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
1.5 mi from city centre
Free Wi-Fi
Air Conditioning
$328
Avg. per night
View Deal

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 June 12, 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 June 12, 2025.

  • How much does a vacation rental in Chestertown cost?

    $337 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 $317 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 January, and the cheapest time to book is March.

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