Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
May 23 - May 24
Tomorrow
May 24 - May 25
This weekend
May 23 - May 25
Next weekend
May 30 - Jun 1

Where to stay in Chestertown?

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
The price is $175
$194 total
includes taxes & fees
May 25 - May 26
Pine Tree Motel & Cabins
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 hotels in Chestertown are cheapest in September

See average prices and weather for all months

Price trends for hotels in Chestertown

Pricing is based on two traveler single night rates
May
$495
Average price during May is $495
Jun
$462
Average price during June is $462
Jul
$419
Average price during July is $419
Aug
$460
Average price during August is $460
Sep
$372
Average price during September is $372
Oct
$391
Average price during October is $391
Nov
$401
Average price during November is $401
Dec
$398
Average price during December is $398
Jan
$498
Average price during January is $498
Feb
$485
Average price during February is $485
Mar
$485
Average price during March is $485
Apr
$442
Average price during April is $442
Currently viewing crowd sizes and weather for May.

May

trending_downLow crowds
High 19°C / low 7°C. Sunny most days.
19°
weather_sun
May, Low crowds, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
23°
weather_sun
June, High crowds, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
27°
weather_sun
July, High crowds, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
26°
weather_sun
August, High crowds, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
22°
weather_sun
September, Moderate crowds, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
14°
weather_cloudy
October, High crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
5°
7°
weather_partly_sunny
November, Low crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
1°
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December, Moderate crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
-2°
ac_unit
January, Low crowds, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
-1°
ac_unit
February, Moderate crowds, average high temperature -1 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
-10°
4°
ac_unit
March, Low crowds, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
11°
weather_cloudy
April, Moderate crowds, average high temperature 11 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
1°
Monthly weather averages (˚C)
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Top landmarks in Chestertown

Friends Lake

Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

See properties in Friends Lake
Friends Lake

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

Frequently asked questions

What accommodations do travelers like in Chestertown?
Friends Lake Inn 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 61 vacation homes. In addition, there are 8 apartments and 7 condos.
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.