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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 ($124). Conversely, the most expensive month to stay in Chestertown is June ($288).

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

The cheapest day to stay in Chestertown is Sunday ($116). On the other hand, travellers can expect to pay the most on Monday, when the average nightly price is $270.

How far ahead should you book a hotel in Chestertown?

Save money by booking a hotel at least 12 days before your trip to Chestertown. The lowest price found when booking 12 days ahead was $101 per night.

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Cheapest hotels in Chestertown, MD

At the moment, these hotels offer the lowest nightly rate out of those we've come across in Chestertown. Consider alternative dates if you're able 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
$98
Avg. per night
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Facts about staying in Chestertown, MD

  • What are the best hotels in Chestertown?

    Circa 1900 Home in the Heart of Historic Downtown Chestertown (10.0/10 from 65 reviews), Comfort Inn and Suites Chestertown (8.2/10 from 295 reviews), and Brampton 1860 (9.2/10 from 39 reviews) are all highly rated places to stay in Chestertown.

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

    In addition to Chestertown, travellers opt to visit Gaithersburg when visiting Maryland. Owings Mills is also a popular choice to visit.

  • How many hotels are there in Chestertown?

    In total, there are 50 hotels to choose from in Chestertown, compared to 11,683 properties in Maryland.

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