Holiday rentals in Chestertown, Maryland

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Other accommodations in Chestertown, MD

Find the perfect holiday rental for your stay in Chestertown, MD. There are 55 hotels in Chestertown, MD and price data was last updated on 26 July 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
$115
Avg. per night
View Deal

Where to stay in Chestertown, MD

Explore different neighbourhoods and areas within Chestertown to find the perfect location for your stay. Map data was last updated on 26 July 2025.
Utilise the map to find properties close to the Chestertown area(s) or attractions you plan on visiting. More information on a given holiday rental can be accessed by clicking the holiday rental's name within the map.

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 26 July 2025.

  • How much does a holiday rental in Chestertown cost?

    $458/night is a typical cost for a holiday rental in Chestertown throughout the year. Rental prices do vary though, and you’ll find that April is the most expensive month to book, and March is the cheapest month to book. HotelsCombined users recently found Chestertown holiday rentals for as low as $199/night. In general, any Chestertown rental for $424 or less is a good deal.

Find better results for your stay in Chestertown, MD

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