Photo by Assya A

Hotels in Chestertown

Free cancellation options if plans change
Unlock travel rewards with One Key
Save more with Member Prices

Check prices for these dates

Tonight
May 17 - May 18
Tomorrow
May 18 - May 19
Next weekend
May 23 - May 25
In two weeks
May 30 - Jun 1

Where to stay in Chestertown?

Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (763)
$114 nightly
The price is $126
Jun 15 - Jun 16
Total includes taxes and fees
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.
trending_down

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
May
$120
Average price during May is $120
Jun
$117
Average price during June is $117
Jul
$102
Average price during July is $102
Aug
$114
Average price during August is $114
Sep
$120
Average price during September is $120
Oct
$109
Average price during October is $109
Nov
$111
Average price during November is $111
Dec
$90
Average price during December is $90
Jan
$89
Average price during January is $89
Feb
$85
Average price during February is $85
Mar
$107
Average price during March is $107
Apr
$97
Average price during April is $97
Currently viewing crowd sizes and weather for May.

May

trending_upHigh crowds
High 71°F / low 56°F. Sunny most days.
71°
weather_sun
May, High crowds, average high temperature 71 degrees Fahrenheit, average low temperature 56 degrees Fahrenheit. Sunny most days.
56°
79°
weather_sun
June, High crowds, average high temperature 79 degrees Fahrenheit, average low temperature 65 degrees Fahrenheit. Sunny most days.
65°
85°
weather_sun
July, Moderate crowds, average high temperature 85 degrees Fahrenheit, average low temperature 71 degrees Fahrenheit. Sunny most days.
71°
83°
weather_sun
August, High crowds, average high temperature 83 degrees Fahrenheit, average low temperature 69 degrees Fahrenheit. Sunny most days.
69°
77°
weather_sun
September, High crowds, average high temperature 77 degrees Fahrenheit, average low temperature 63 degrees Fahrenheit. Sunny most days.
63°
66°
weather_sun
October, Moderate crowds, average high temperature 66 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
54°
weather_sun
November, Moderate crowds, average high temperature 54 degrees Fahrenheit, average low temperature 41 degrees Fahrenheit. Sunny most days.
41°
46°
weather_partly_sunny
December, Low crowds, average high temperature 46 degrees Fahrenheit, average low temperature 35 degrees Fahrenheit. Partly sunny.
35°
40°
weather_partly_sunny
January, Low crowds, average high temperature 40 degrees Fahrenheit, average low temperature 29 degrees Fahrenheit. Partly sunny.
29°
43°
weather_partly_sunny
February, Low crowds, average high temperature 43 degrees Fahrenheit, average low temperature 30 degrees Fahrenheit. Partly sunny.
30°
51°
weather_partly_sunny
March, Low crowds, average high temperature 51 degrees Fahrenheit, average low temperature 37 degrees Fahrenheit. Partly sunny.
37°
62°
weather_sun
April, Moderate crowds, average high temperature 62 degrees Fahrenheit, average low temperature 47 degrees Fahrenheit. Sunny most days.
47°
Monthly weather averages (˚F)
View all properties

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 Sumner Hall 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
A tranquil hotel pool encircled by beautiful arches, enhancing the ambiance for leisure and relaxation.

Summer Getaway Sale

Save 25% or more on select hotels, and earn 50% more rewards on all properties. Book by May 26 and travel by Sep 30, 2025. See terms*
Sign in or join for free

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.
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 25 vacation homes. In addition, you can choose from 8 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.

Terms and conditions

*Book by 5/26/2025 11:59 pm in hotel property local time. Stay between 4/17/2025-9/30/2025. Member Prices are available to Hotels.com® app users and One Key members. Limited availability, blackout periods may apply.

OneKeyCash is not redeemable for cash and can only be used on Hotels.com®, Expedia®, and Vrbo®.

https://www.hotels.com/lp/b/deals