Holiday rentals in Chestertown, Maryland

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Travel insights for holiday rentals in Chestertown

Use our HotelsCombined data-powered tips to help you find your next holiday 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 (£98). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is £207.
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Where to stay in Chestertown

Explore different neighbourhoods and areas within Chestertown, MD to find the perfect location for your stay. Map data was last updated on 12 September 2025.
Scroll through the map to find holiday rentals close to the Chestertown neighbourhood(s) 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 12 September 2025.

  • How much does a holiday rental in Chestertown cost?

    Chestertown holiday rentals are £203/night on average. However, you may find that prices fluctuate depending on the time of year. For example, April is the most expensive month to book a holiday rental in Chestertown, and March is often the cheapest month to book. Recently, our users found rentals for £89/night - which is currently the cheapest price. Keep in mind that anything £191/night or less is still considered a good deal.

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Consider other places to stay in Chestertown

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