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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 January (€67). Conversely, the most expensive month to stay in Chestertown is September (€179).

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

The cheapest day to stay in Chestertown is Tuesday (€88). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is €212.
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Cheapest hotels in Chestertown, MD

Discover affordable stays in Chestertown, MD that provide a quality experience without breaking the bank. Hotels in Chestertown, MD can be found for as low as €59 per night. There is currently one property in Chestertown, MD that can be booked for this price. Driftwood Inn is one of the hotels that can be booked for the lowest price in Chestertown, MD. Price data was last updated on July 6, 2025
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
€59
Avg. per night
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Where to stay in Chestertown, MD

Explore different neighborhoods and areas within Chestertown to find the perfect location for your stay. Map data was last updated on July 6, 2025.
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

Find useful tips and insights about staying in Chestertown to help you make the most of your experience. FAQs were last updated on July 6, 2025.

  • What are the best hotels in Chestertown?

    234 reviews rated Comfort Inn and Suites Chestertown with an average score of 8.0/10. It may also be worth looking into the Brampton 1860, which received a rating of 9.7/10 from 41 reviews. Carriage House Hideaway In Center of Chestertown could also be a good option, with a score of 9.9/10 from 55 reviews.

  • 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 43 hotels to choose from in Chestertown, compared to 14,157 properties in Maryland.

Find better results for your stay in Chestertown, MD

Consider these popular 5-star hotels in Chestertown

Stay at one of these Chestertown 5-star hotels that users have found on HotelsCombined.
Brampton 1860