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Vacation rentals in Chestertown, MD

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Other accommodations in Chestertown, MD

Find the perfect vacation rental for your stay in Chestertown, MD. There are 43 hotels in Chestertown, MD and price data was last updated on 5 June 2025. The average price for a hotel in Chestertown, MD is .
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Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
C$ 94
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 5 June 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 5 June 2025.

  • How much does a vacation rental in Chestertown cost?

    Chestertown vacation rentals are C$ 457/night on average. However, you may find that prices fluctuate depending on the time of year. For example, January is the most expensive month to book a vacation rental in Chestertown, and March is often the cheapest month to book. Recently, our users found rentals for C$ 164/night - which is currently the cheapest price. Keep in mind that anything C$ 425/night or less is still considered a good deal.

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