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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 January (S$ 151). Conversely, the most expensive month to stay in Chestertown is September (S$ 407).

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

The cheapest day to stay in Chestertown is Tuesday (S$ 200). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is S$ 509.
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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 S$ 88 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 12 July 2025
These are the lowest prices we've found on hotels in Chestertown at the moment. As prices can vary by date, change the dates if you're flexible to compare rates.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
S$ 88
Avg. per night
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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 12 July 2025.

  • What are the best hotels in Chestertown?

    One of the most popular hotels in Chestertown is Comfort Inn and Suites Chestertown, which has been reviewed by 234 users and currently has a rating of 8.0/10. Other top-rated locations include Brampton 1860 and Carriage House Hideaway In Center of Chestertown, which have received 9.7/10 and 9.9/10 ratings from our users, respectively.

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

    In addition to Chestertown, travellers opt to visit Bethesda when visiting Maryland. Takoma Park 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 15,858 properties in Maryland.

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