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Hotels in Chestertown, MD

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Travel insights for hotels in Chestertown

Use our HotelsCombined data-powered tips to help you find your next hotel in Chestertown.

What is the cheapest month to book a hotel in Chestertown?

The cheapest month to book a hotel in Chestertown is July ($88). Conversely, the most expensive month to stay in Chestertown is December ($263).

What is the cheapest day to stay in a hotel in Chestertown?

The cheapest day to stay in Chestertown is Sunday ($86). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $200.

How far ahead should you book a hotel in Chestertown?

Save money by booking a hotel at least 22 days before your trip to Chestertown. The lowest price found when booking 22 days ahead was $70 per night.

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Cheapest hotels in Chestertown, MD

These are the lowest prices we've found on hotels in Chestertown at the moment. If you have flexibility with arrival and departure, use the search form to compare prices for other dates.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.0 mi from city centre
Free Wi-Fi
Parking
$69
Avg. per night
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Where to stay in Chestertown

Scroll through the map to find hotels close to the Chestertown neighborhood(s) you plan on visiting. Clicking on a hotel name will take you to a page with pricing, reviews, and more useful information.

Facts about staying in Chestertown, MD

  • What are the best hotels in Chestertown?

    287 reviews rated Comfort Inn and Suites Chestertown with an average score of 8.1/10. It may also be worth looking into the Brampton 1860, which received a rating of 9.1/10 from 39 reviews. First Floor Studio Apartment in Historic Chestertown could also be a good option, with a score of 9.5/10 from 99 reviews.

  • How much is a cheap hotel in Chestertown?

    $68 per night is the cheapest Chestertown hotel price found in our data from the last 72 hours.

  • What are some other cities to stay in when visiting Maryland?

    In addition to Chestertown, travelers opt to visit Ocean City when visiting Maryland. Baltimore is also a popular choice to visit.

  • How many hotels are there in Chestertown?

    In total, there are 46 hotels to choose from in Chestertown, compared to 11,956 properties in Maryland.

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Find better results for your stay in Chestertown, MD

Consider these popular 5-star hotels in Chestertown

Brampton 1860