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Hotels in Chestertown, Maryland

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Travel insights for hotels in Chestertown

Use these up-to-date, data-driven insights about booking a hotel in Chestertown including ideal times to book, pricing trends, and more.

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, travellers can expect to pay the most on Monday, when the average nightly price is $177.

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 the flexibility, change the dates selected to compare prices.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
$69
Avg. per night
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Facts about staying in Chestertown, MD

  • What are the best hotels in Chestertown?

    Comfort Inn and Suites Chestertown, rated with a score of 8.1 from 288 reviewers, is one of the most popular hotels in Chestertown. Other top stays include First Floor Studio Apartment in Historic Chestertown, with an average rating of 9.5 from 99 reviewers, and Brampton 1860, with a score of 9.2 from 39 reviewers.

  • How much is a cheap hotel in Chestertown?

    HotelsCombined searches in the last 3 days suggest cheap Chestertown hotels have prices starting from as low as $73/night, depending on the popularity of your requested dates.

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

    In addition to Chestertown, travellers opt to visit Baltimore when visiting Maryland. Silver Spring is also a popular choice to visit.

  • How many hotels are there in Chestertown?

    In total, there are 47 hotels to choose from in Chestertown, compared to 11,972 properties in Maryland.

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