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Vacation rentals in Chestertown, MD

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Travel insights for vacation rentals in Chestertown

Use these up-to-date, data-driven insights about booking a vacation rental in Chestertown including ideal times to book, pricing trends, and more.

What is the cheapest day to stay in a vacation rental in Chestertown?

The cheapest day to stay in Chestertown is Sunday (C$ 203). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is C$ 676.

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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 décembre 2025.
Navigate to the areas in Chestertown you plan to visit to find vacation rentals that are close by. Users can click on a vacation rental's name to find more information about it, such as price, reviews, and amenities, and also find different deals for the property.

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 décembre 2025.

  • How much does a vacation rental in Chestertown cost?

    Chestertown vacation rentals are C$ 418/night on average. However, you may find that prices fluctuate depending on the time of year. For example, August is the most expensive month to book a vacation rental in Chestertown, and November is often the cheapest month to book. Recently, our users found rentals for C$ 192/night - which is currently the cheapest price. Keep in mind that anything C$ 392/night or less is still considered a good deal.

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