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Hotels in Chestertown

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Check prices for these dates

Tonight
Mar 6 - Mar 7
Tomorrow
Mar 7 - Mar 8
This weekend
Mar 7 - Mar 9
Next weekend
Mar 14 - Mar 16

Where to stay in Chestertown?

Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.4 out of 10, Good, (335)
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.
data_trends

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 traveller single night rates
Mar
CA $172
Average price during March is CA $172
Apr
CA $153
Average price during April is CA $153
May
CA $186
Average price during May is CA $186
Jun
CA $183
Average price during June is CA $183
Jul
CA $173
Average price during July is CA $173
Aug
CA $216
Average price during August is CA $216
Sep
CA $179
Average price during September is CA $179
Oct
CA $191
Average price during October is CA $191
Nov
CA $177
Average price during November is CA $177
Dec
CA $135
Average price during December is CA $135
Jan
CA $123
Average price during January is CA $123
Feb
CA $122
Average price during February is CA $122
Currently viewing crowd sizes and weather for March.

March

trending_downLow crowds
High 11°C / low 3°C. Partly sunny.
11°
weather_partly_sunny
March, Low crowds, average high temperature 11 degrees Celsius, average low temperature 3 degrees Celsius. Partly sunny.
3°
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°
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 Rolphs Wharf Marina and Historical Society of Kent County Maryland. The city has something for everyone including sights like Garfield Center for the Arts at the Prince Theater and Kings Town Park within a small-town setting.

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Photo by Assya A
Open Photo by Assya A

Frequently asked questions

Where can I get free parking with my stay in Chestertown?
These hotels offer the perk of free parking: Driftwood Inn, Red Roof Inn & Suites Chestertown and Comfort Inn & Suites Chestertown. There are 5 options you may want to check out on our site.
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 with my pet in Chestertown?
Your animal companion is welcome at these pet-friendly hotels: Comfort Inn & Suites Chestertown, Red Roof Inn & Suites Chestertown, and Driftwood Inn.
Where should I consider staying in Chestertown if I'm looking for a cheap accommodation?
Two inexpensive options worth considering are Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.
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 7 apartments.
Where can I stay if I'm visiting Chestertown with my kids?
Parents traveling with children may want to consider Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown.
Where should I stay in Chestertown for a getaway with my partner?
Red Roof Inn & Suites Chestertown is a great option for a romantic getaway.
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.