Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Nov 27 - Nov 28
Tomorrow
Nov 28 - Nov 29
This weekend
Nov 28 - Nov 30
Next weekend
Dec 5 - Dec 7

Where to stay in Chestertown?

Lake view
The Fern Lodge
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (50)
The price is $599
$665 total
includes taxes & fees
Nov 28 - Nov 29
The Fern Lodge
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 September
Price trends for hotels in Chestertown
Pricing is based on two traveler single night rates
View properties in November
Currently viewing crowd sizes and weather for November.
Typical weather for Chestertown
November
Low crowds
High 7°C / low -1°C. Partly sunny.
View properties in November
7°
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November, Low crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
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1°
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December, Moderate crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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-2°
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January, Low crowds, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
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-1°
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February, Moderate crowds, average high temperature -1 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
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4°
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March, Low crowds, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
11°
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April, Moderate crowds, average high temperature 11 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
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19°
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May, Low crowds, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
23°
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June, High crowds, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
27°
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July, High crowds, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
26°
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August, High crowds, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
22°
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September, Moderate crowds, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
14°
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October, High crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
5°
Monthly weather averages (˚C)

Top neighborhoods in Chestertown

Chester Shores

Chestertown's Chester Shores neighborhood offers attractions including Loon Lake.

Top landmarks in Chestertown

Loon Lake

Loon Lake is 3.2 mi (5.2 km) from central Chestertown, why not stop by during your stay.
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Friends Lake

Friends Lake is 2.8 mi (4.5 km) from central Chestertown, why not stop by during your stay.
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Learn more about Chestertown

Chestertown is well-known for its attractions such as Loon Lake Beach and Friends Lake. The city has something for everyone including sights like Loon Lake and Hudson River within a secluded setting.

See all hotels in Chestertown
A winter scene
Photo by Julie Miller
Open Photo by Julie Miller

Check out reviews of Chestertown hotels guests love

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"Wonderful hotel, with lots of old charm!"
Robert 1-night trip
Posted 15 hours ago
The Queensbury Hotel

Frequently asked questions

What accommodations do travelers like in Chestertown?
The Fern Lodge is an accommodation that is popular with guests.
Can I book a refundable accommodation in Chestertown?
If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates you can book. You can see these accommodations 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're looking for a good alternative to a hotel, look over our selection of 58 vacation homes. You can also consider one of the 7 apartments or 17 cottages.
What will the weather in Chestertown be like during my visit?
The warmest months in Chestertown are usually July and August with an average temp of 65°F. January and February are the chilliest months when the average temp is 25°F. The rainiest months are June and July.
Why should I book my Chestertown hotel with Hotels.com?
There are plenty of reasons to book your Chestertown travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, 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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