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Chestertown, United States
1 May — 2 May2
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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 (£52). Conversely, the most expensive month to stay in Chestertown is September (£123).
What is the cheapest day to stay in a hotel in Chestertown?
The cheapest day to stay in Chestertown is Tuesday (£55). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is £160.
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 £52 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 24 April 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.
Find the perfect hostel, theme hotel, or holiday rental for your stay in Chestertown, MD. There are 42 hotels in Chestertown, MD and price data was last updated on 24 April 2025. The average price for a stay in Chestertown, MD is £113/night.
Find useful tips and insights about staying in Chestertown to help you make the most of your experience. FAQs were last updated on 24 April 2025.
What are the best hotels in Chestertown?
Comfort Inn and Suites Chestertown is a very popular hotel in Chestertown, with a score of 7.9 from 220 reviews. Red Roof Inn & Suites Chestertown (7.2 from 32 reviews) and Brampton 1860 (9.4 from 37 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. Silver Spring is also a popular choice to visit.
How many hotels are there in Chestertown?
In total, there are 42 hotels to choose from in Chestertown, compared to 14,063 properties in Maryland.
Find better results for your stay in Chestertown, MD
Consider alternative stays in Chestertown
If you are looking for a specific type of hotel, consider these options for trips to Chestertown
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