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Vacation rentals in Chestertown, MD

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Chestertown, United States
May 7 — May 82
...and more

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Other accommodations in Chestertown, MD

Find the perfect vacation rental for your stay in Chestertown, MD. There are 42 hotels in Chestertown, MD and price data was last updated on April 30, 2025. The average price for a hotel in Chestertown, MD is .
Show all 42 stays
Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
1.5 mi from city centre
Free Wi-Fi
Air Conditioning
$307
Avg. per night
View Deal
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.0 mi from city centre
Free Wi-Fi
Parking
$69
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 April 30, 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 30, 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 $286 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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