Hotels in Chestertown

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Check prices for these dates

Tonight
Dec 21 - Dec 22
Tomorrow
Dec 22 - Dec 23
Next weekend
Dec 26 - Dec 28
In two weeks
Jan 2 - Jan 4

Where to stay in Chestertown?

Free daily full breakfast
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (860)
The price is CNY739
CNY820 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Comfort Inn & Suites Chestertown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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When is the best time to visit Chestertown?

Our prices for hotels in Chestertown are cheapest in January
Price trends for hotels in Chestertown
Pricing is based on two traveler single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Chestertown
December
Low crowds
High 8°C / low 2°C. Partly sunny.
View properties in December
8°
weather_partly_sunny
December, Low crowds, average high temperature 8 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
4°
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January, Low crowds, average high temperature 4 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
-2°
6°
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February, Low crowds, average high temperature 6 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
11°
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March, Low crowds, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
17°
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April, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
22°
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May, High crowds, average high temperature 22 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
26°
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June, High crowds, average high temperature 26 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
29°
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July, Moderate crowds, average high temperature 29 degrees Celsius, average low temperature 22 degrees Celsius. Sunny most days.
22°
28°
weather_sun
August, High crowds, average high temperature 28 degrees Celsius, average low temperature 21 degrees Celsius. Sunny most days.
21°
25°
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September, High crowds, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
19°
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October, Moderate crowds, average high temperature 19 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
12°
weather_sun
November, Moderate crowds, average high temperature 12 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
Monthly weather averages (˚C)

Top landmarks in Chestertown

Washington College

4.1/5 (45 reviews)
If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.
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River Arts Chestertown

If you'd like to get a taste of Chestertown student life, check out River Arts Chestertown, located 0.7 mi (1.1 km) from central Chestertown.
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Learn more about Chestertown

Notable for its university life, Chestertown features attractions such as Historical Society of Kent County Maryland and Chestertown Historic District. The city has something for everyone including sights like Crumpton Auction and Northern Chesapeake Bay within a small-town setting.

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Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Check out reviews of Chestertown hotels guests love

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

10/10 Excellent
"Room was very nice. Staff is always very nice."
Peggy 1-night trip
Posted 2 days ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Frequently asked questions

How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from CNY402 with options to suit your budget and needs. To find an affordable hotel in Chestertown that meets all of your requirements, just apply filters on Hotels.com and sort hotels by "Price: low to high".
How can I find deals and earn rewards at Chestertown hotels?
Discover great deals on Chestertown hotel stays with Hotels.com. It's also a good idea to look at hotel prices mid-week or during the low season as you're likely to find off-peak deals. And make sure to check out our last-minute deals on Chestertown hotels.
Can I book Chestertown hotels with free cancellation?
In order to book a refundable Chestertown hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are the top Chestertown hotels with a pool?
Discover some of the best Chestertown hotels with a pool for a little extra luxury on your trip. The Lodge at Great Oak Landing is a great lodge with a seasonal outdoor pool and a guest rating of 8 out of 10. Plus, you can make the most of its private beach (direct access) and restaurant. You can select "Pool" in the "Amenities" filter of your search on Hotels.com to find even more places to stay in Chestertown with a pool.
What are some of the best Chestertown hotels with free parking?
If you're exploring by car, finding a great Chestertown hotel with free parking is a win. Our travelers' favorites include:
What hotels do travelers recommend in Chestertown?
Comfort Inn & Suites Chestertown, The Lodge at Great Oak Landing and Driftwood Inn are all properties that our guests really like.
Can I book a refundable hotel in Chestertown?
If you're looking for the flexibility to change your plans to Chestertown, most properties offer refundable* rates you can book. You can find these properties by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Chestertown if I want a vacation home instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 23 vacation homes. In addition, you can choose from 6 apartments.
What will the weather in Chestertown be like during my trip?
July and August are typically the warmest months in Chestertown when the average temp is 74°F. January and February are the coldest months when the average temperature is 39°F. August and July are the months with the most rain.
Why should I book my Chestertown hotel with Hotels.com?
There are lots of reasons to book your Chestertown trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

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