Hotels in Chestertown, MD

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Chestertown, MD, United States
Mar 26 — Mar 272
Chestertown, MD, United States
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Popular hotels in Chestertown, MD

Discover well-known properties in Chestertown, MD that are favored by visitors more than others. There are 42 hotels in Chestertown, MD and price data was last updated on March 19, 2024. The average price for a hotel in Chestertown, MD is $155/night.
These are some of the hotels in Chestertown with the highest demand. Users can utilize the filters available to narrow down their search.
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25227 Chestertown Road, Chestertown, MD, United States
Brampton Bed and Breakfast Inn provides a comfortable setting while in Chestertown. It also features a concierge, free Wi-Fi and meeting rooms.
Free Wi-Fi
Air Conditioning
9.5
Excellent
33 reviews
Location
1.5 mi from city centre
609 Washington Avenue, Chestertown, MD, United States
Driftwood Inn is a rustic motel situated a short drive from Rock Hall. Popular amenities, such as free Wi-Fi and a Jacuzzi, ensure a satisfying stay in Chestertown.
Free Wi-Fi
Parking
5.7
Okay
98 reviews
Location
1.0 mi from city centre

Tips for booking hotels in Chestertown, MD

Gain useful insights and advice for booking the perfect stay in Chestertown, MD. Price data is based on averages over the past 12 months and was last updated on March 19, 2024.
Cheapest month:January
Most expensive month:May
Average price in Chestertown:$155/night
Cheapest price found:$76/night
Cheapest day:Friday
Most expensive day:Thursday
$107 - $233
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.
$106 - $173
Average price per night / 3-star hotel. Prices are not fixed and may vary with time.

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 19, 2024.
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.
2 stars
2 stars and under
609 Washington Avenue, Chestertown, MD, United States
4 stars
4 stars +
25227 Chestertown Road, Chestertown, MD, United States

Best prices found by HotelsCombined users in the past 24 hours.

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 19, 2024. The average price for a stay in Chestertown, MD is $155/night.
Show all 42 stays
25227 Chestertown Road, Chestertown, MD, United States
1.5 mi from city centre
Free Wi-Fi
Air Conditioning
$243
Avg. per night

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 19, 2024.
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 19, 2024.
  • What are the best hotels in Chestertown?

    283 reviews rated Comfort Inn and Suites Chestertown with an average score of 7.5/10. It may also be worth looking into the Red Roof Inn & Suites Chestertown, which received a rating of 7.2/10 from 18 reviews. Brampton Bed and Breakfast Inn could also be a good option, with a score of 9.5/10 from 33 reviews.

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