Vacation rentals in Chestertown, MD

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Other accommodations in Chestertown

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 enero 6, 2026. 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
View Deal

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 enero 6, 2026.
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 enero 6, 2026.

  • How much does a vacation rental in Chestertown cost?

    $272 per night is how much a vacation rental in Chestertown costs, on average. $113 per night was the cheapest price recently found by our users, though anything for $248 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 August, and the cheapest time to book is December.

Find better results for your stay in Chestertown, MD

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