Holiday rentals in Chestertown, Maryland

Search and compare Chestertown, Maryland holiday rentals from hundreds of travel sites on HotelsCombined and save.

...and more

Learn why travellers love HotelsCombined

Compare hotel ratings collected from thousands of user reviews.

One search gives you accurate pricing on affordable hotels.

Customie your results by hotel chain, amenities, price and more.

Search for hotels as many times as you want – for free.

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
$99
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.
Utilise the map to find properties close to the Chestertown area(s) or attractions you plan on visiting. Clicking a property's name will unlock more information and allow you to book that particular holiday 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?

    $435 per night is how much a holiday rental in Chestertown costs, on average. $163 per night was the cheapest price recently found by our users, though anything for $406 per night or less is a good deal. Keep in mind that Chestertown holiday rental prices fluctuate throughout the year: the most expensive month to book is August, and the cheapest time to book is December.

Find better results for your stay in Chestertown, MD