Holiday rentals in Chestertown, Maryland

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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 28 January 2026.
Navigate to the areas in Chestertown you plan to visit to find vacation rentals that are close by. As an added benefit, users can click a vacation rental they're interesting in to find helpful information and deals for that vacation rental.

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 28 January 2026.

  • How much does a holiday rental in Chestertown cost?

    The average cost for a holiday rental in Chestertown is $302/night. A good holiday rental deal in Chestertown would be for $282/night or less. The cheapest rental deal found recently by our users was $113/night. If you’re flexible with your travel dates, then try to avoid booking August, the most expensive month of the year. Booking December is the cheapest month to book a holiday rental in Chestertown.

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