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Hotels in Chestertown, MD

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Chestertown, United States
Mar 17 — Mar 182
...and more

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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 ($92). Conversely, the most expensive month to stay in Chestertown is September ($218).

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

The cheapest day to stay in Chestertown is Tuesday ($114). On the other hand, travelers can expect to pay the most on Friday, when the average nightly price is $285.

How far ahead should you book a hotel in Chestertown?

Save money by booking a hotel at least 14 days before your trip to Chestertown. The lowest price found when booking 14 days ahead was $76 per night.
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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 $69 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 March 10, 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.
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Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
1.0 mi from city centre
Free Wi-Fi
Parking
$69
Avg. per night
View Deal
Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
1.5 mi from city centre
Free Wi-Fi
Air Conditioning
$277
Avg. per night
View Deal

Hotel prices in Chestertown, MD

Get a sense of the average price and most popular properties to stay in Chestertown to help you budget for your trip accordingly. Hotels that are booked the most in each class receive the “Most popular” badge. Hotels with the “Best value” badge are the most popular hotels in Chestertown at attractive prices. Price data was last updated on March 10, 2025.
Some of the best options for booking a hotel in Chestertown categorized by hotel class. We've highlighted the most popular properties according to our users as well as the best value within each hotel class.
4 stars +
Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
$277
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2 stars and under
Driftwood Inn
Driftwood Inn

Driftwood Inn

609 Washington Avenue, Chestertown, MD, United States
$69
View Deal

Other accommodations in Chestertown, MD

Find the perfect hostel, theme hotel, or vacation rental for your stay in Chestertown, MD. There are 42 hotels in Chestertown, MD and price data was last updated on March 10, 2025. The average price for a stay in Chestertown, MD is $151/night.
Show all 42 stays
Brampton 1860
Brampton 1860

Brampton 1860

25227 Chestertown Road, Chestertown, MD, United States
1.5 mi from city centre
Free Wi-Fi
Air Conditioning
$277
Avg. per night
View Deal

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 March 10, 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 March 10, 2025.

  • What are the best hotels in Chestertown?

    217 reviews rated Comfort Inn and Suites Chestertown with an average score of 7.9/10. It may also be worth looking into the Red Roof Inn & Suites Chestertown, which received a rating of 7.1/10 from 31 reviews. Brampton 1860 could also be a good option, with a score of 9.6/10 from 36 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 42 hotels to choose from in Chestertown, compared to 13,952 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