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Hotels in Chestertown, Maryland

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Chestertown, United States
1 May — 2 May2
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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 ($227). Conversely, the most expensive month to stay in Chestertown is September ($534).

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

The cheapest day to stay in Chestertown is Tuesday ($240). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $694.
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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 $108 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. Consider alternative dates if you're able to compare prices.
Show all 42 hotels
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.5 km from city centre
Free Wi-Fi
Parking
$108
Avg. per night
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Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
2.5 km from city centre
Free Wi-Fi
Air conditioning
$457
Avg. per night
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Other accommodations in Chestertown, MD

Find the perfect hostel, theme hotel, or holiday rental for your stay in Chestertown, MD.
Show all 42 stays
Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
2.5 km from city centre
Free Wi-Fi
Air conditioning
$457
Avg. per night
View Deal

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 24 April 2025.

  • What are the best hotels in Chestertown?

    Comfort Inn and Suites Chestertown (7.9/10 from 220 reviews), Red Roof Inn & Suites Chestertown (7.2/10 from 32 reviews), and Brampton 1860 (9.4/10 from 37 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 Baltimore when visiting Maryland. National Harbor 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
Holiday rentals in Chestertown, Maryland