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 43 hotels in Chestertown, MD and price data was last updated on 28 January 2026. 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
₹ 6,323
Avg. per night
View Deal

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. Clicking on a vacation rental name will take you to a page with pricing, reviews, and more useful information.

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?

    A holiday rental in Chestertown will cost ₹ 27,661 per night on average. However some users found rentals for as low as ₹ 10,372 per night. A good deal on a Chestertown holiday rental would be anything for ₹ 25,825 per night or less. Keep in mind that booking August may be more expensive, whereas booking December is the cheapest month of the year to book.

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