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Hotels in Chestertown

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Check prices for these dates

Tonight
Apr 30 - May 1
Tomorrow
May 1 - May 2
This weekend
May 2 - May 4
Next weekend
May 9 - May 11

Where to stay in Chestertown?

Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout drapes, iron/ironing board

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (346)
The price is $68
$76 total
includes taxes & fees
May 7 - May 8
Red Roof 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 hotels in 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
Apr
$111
Average price during April is $111
May
$131
Average price during May is $131
Jun
$170
Average price during June is $170
Jul
$129
Average price during July is $129
Aug
$155
Average price during August is $155
Sep
$125
Average price during September is $125
Oct
$132
Average price during October is $132
Nov
$136
Average price during November is $136
Dec
$96
Average price during December is $96
Jan
$84
Average price during January is $84
Feb
$81
Average price during February is $81
Mar
$132
Average price during March is $132
Currently viewing crowd sizes and weather for April.

April

trending_flatModerate crowds
High 17°C / low 8°C. Sunny most days.
17°
weather_sun
April, Moderate crowds, average high temperature 17 degrees Celsius, average low temperature 8 degrees Celsius. Sunny most days.
8°
22°
weather_sun
May, High crowds, average high temperature 22 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
26°
weather_sun
June, High crowds, average high temperature 26 degrees Celsius, average low temperature 18 degrees Celsius. Sunny most days.
18°
29°
weather_sun
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°
19°
weather_sun
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°
8°
weather_partly_sunny
December, Low crowds, average high temperature 8 degrees Celsius, average low temperature 2 degrees Celsius. Partly sunny.
2°
4°
weather_partly_sunny
January, Low crowds, average high temperature 4 degrees Celsius, average low temperature -2 degrees Celsius. Partly sunny.
-2°
6°
weather_partly_sunny
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°
Monthly weather averages (˚C)
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Top landmarks in Chestertown

Washington College

If you'd like to get a taste of Chestertown student life, check out Washington College, in the heart of the town.

See properties in Washington College
Washington College

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 Garfield Center for the Arts at the Prince Theater and Crumpton Auction within a small-town setting.

See all hotels in Chestertown
Somewhere over the rainbow... Terrific view on the plane back to the North.
Photo by Assya A
Open Photo by Assya A

Frequently asked questions

What hotels do travelers recommend in Chestertown?
Comfort Inn & Suites Chestertown, The Lodge at Great Oak Landing and Red Roof Inn & Suites Chestertown 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 26 vacation homes. In addition, you can choose from 8 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.