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Hotels in Chestertown

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Check prices for these dates

Tonight
Oct 17 - Oct 18
Tomorrow
Oct 18 - Oct 19
This weekend
Oct 17 - Oct 19
Next weekend
Oct 24 - Oct 26

Where to stay in Chestertown?

Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (829)
The price is $102
$113 total
includes taxes & fees
Oct 19 - Oct 20
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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Our prices for Chestertown are cheapest in February

See average prices and weather for all months
Price trends for hotels in Chestertown
Pricing is based on two traveler single night rates
View properties in October
Currently viewing crowd sizes and weather for October.
Weather forecast for Chestertown
October
Moderate crowds
High 19°C / low 12°C. Sunny most days.
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19°
weather_sun
October, Moderate crowds, average high temperature 19 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
12°
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November, Moderate crowds, average high temperature 12 degrees Celsius, average low temperature 5 degrees Celsius. Sunny most days.
5°
8°
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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°
weather_partly_sunny
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°
weather_sun
September, High crowds, average high temperature 25 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
17°
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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Rolphs Wharf Marina

Imagine strolling along Rolphs Wharf Marina for some great waterfront pics. It's located 3.6 mi (5.8 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 Rolphs Wharf Marina. The city has something for everyone including sights like Chesapeake Bay and Garfield Center for the Arts at the Prince Theater within a small-town setting.

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Somewhere over the rainbow... Terrific view on the plane back to the North.
Photo by Assya A
Open Photo by Assya A

Check out reviews of Chestertown hotels guests love

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"The only criticism I have is that the towels were in terrible condition and even stained"
Sheryl 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

Frequently asked questions

What hotels do travelers recommend in Chestertown?
Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown 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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