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Hotels in Chestertown, Maryland

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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 (£50). Conversely, the most expensive month to stay in Chestertown is September (£135).

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

The cheapest day to stay in Chestertown is Wednesday (£71). On the other hand, travelers can expect to pay the most on Thursday, when the average nightly price is £169.
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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 £51 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 19 August 2025
At the moment, these hotels offer the lowest nightly rate out of those we've come across in Chestertown. Prices will typically fluctuate depending on the dates selected, star rating of hotel, and hotel location.
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
0.9 mi from city centre
Free Wi-Fi
Parking
£51
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 19 August 2025.

  • What are the best hotels in Chestertown?

    Comfort Inn and Suites Chestertown is a very popular hotel in Chestertown, with a score of 8.0 from 243 reviews. Brampton 1860 (9.7 from 41 reviews) and Carriage House Hideaway In Center of Chestertown (9.9 from 69 reviews) are also highly rated Chestertown hotels based on recent feedback from HotelsCombined users.

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

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

  • How many hotels are there in Chestertown?

    In total, there are 55 hotels to choose from in Chestertown, compared to 16,156 properties in Maryland.

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Consider alternative stays in Chestertown

If you are looking for a specific type of hotel, consider these options for trips to Chestertown
Holiday rentals in Chestertown, Maryland

Search cheap hotels with HotelsCombined. Use the hotel finder to search for the cheapest hotel deal for all major destinations around the world. HotelsCombined searches hundreds of hotel booking sites to help you find hotels and book the ones that suit you best. Since HotelsCombined searches many hotel sites at once, you can find discounted hotels quickly, including Hotels Under £37 and Hotels Under £74. Discover hotel discounts now and make your hotel reservation today.