Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Jul 3 - Jul 4
Tomorrow
Jul 4 - Jul 5
This weekend
Jul 4 - Jul 6
Next weekend
Jul 11 - Jul 13

Where to stay in Chestertown?

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (127)
$175 nightly
The price is $194
Jul 6 - Jul 7
Total includes taxes and fees
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.
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Our prices for hotels in Chestertown are cheapest in October

See average prices and weather for all months

Price trends for hotels in Chestertown

Pricing is based on two traveler single night rates
Jul
$412
Average price during July is $412
Aug
$394
Average price during August is $394
Sep
$411
Average price during September is $411
Oct
$368
Average price during October is $368
Nov
$400
Average price during November is $400
Dec
$396
Average price during December is $396
Jan
$441
Average price during January is $441
Feb
$487
Average price during February is $487
Mar
$484
Average price during March is $484
Apr
$450
Average price during April is $450
May
$473
Average price during May is $473
Jun
$428
Average price during June is $428
Currently viewing crowd sizes and weather for July.

July

trending_upHigh crowds
High 80°F / low 59°F. Sunny most days.
80°
weather_sun
July, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
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78°
weather_sun
August, High crowds, average high temperature 78 degrees Fahrenheit, average low temperature 58 degrees Fahrenheit. Sunny most days.
58°
71°
weather_sun
September, Moderate crowds, average high temperature 71 degrees Fahrenheit, average low temperature 51 degrees Fahrenheit. Sunny most days.
51°
57°
weather_cloudy
October, High crowds, average high temperature 57 degrees Fahrenheit, average low temperature 41 degrees Fahrenheit. Cloudy most days.
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44°
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November, Low crowds, average high temperature 44 degrees Fahrenheit, average low temperature 29 degrees Fahrenheit. Partly sunny.
29°
33°
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December, Moderate crowds, average high temperature 33 degrees Fahrenheit, average low temperature 22 degrees Fahrenheit. Snow likely.
22°
28°
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January, Low crowds, average high temperature 28 degrees Fahrenheit, average low temperature 13 degrees Fahrenheit. Snow likely.
13°
30°
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February, Moderate crowds, average high temperature 30 degrees Fahrenheit, average low temperature 14 degrees Fahrenheit. Snow likely.
14°
39°
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March, Low crowds, average high temperature 39 degrees Fahrenheit, average low temperature 22 degrees Fahrenheit. Snow likely.
22°
52°
weather_cloudy
April, Moderate crowds, average high temperature 52 degrees Fahrenheit, average low temperature 33 degrees Fahrenheit. Cloudy most days.
33°
67°
weather_sun
May, Low crowds, average high temperature 67 degrees Fahrenheit, average low temperature 45 degrees Fahrenheit. Sunny most days.
45°
74°
weather_sun
June, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
Monthly weather averages (˚F)
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Top neighborhoods in Chestertown

Chester Shores map

Chester Shores

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

Top landmarks in Chestertown

Friends Lake

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

See properties in Friends Lake
Friends Lake

Learn more about Chestertown

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

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

Check out the Chestertown hotels guests love right now

Clarion Inn & Suites at the Outlets of Lake George

Clarion Inn & Suites at the Outlets of Lake George

10/10 Excellent
"The bed was great pillows sheets ect very clean and keep up to date "
Mark 1-night trip
Posted 2 days ago
Clarion Inn & Suites at the Outlets of Lake George

Frequently asked questions

What accommodations do travelers like in Chestertown?
Friends Lake Inn is an accommodation that is popular with guests.
Where can I find free parking with my stay in Chestertown?
Park your car for free at The Loft at The Remington.
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 with my pet in Chestertown?
Your furry friend can stay with you at these pet-friendly hotels: Pine Tree Motel & Cabins, Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing and Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer.
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 60 vacation homes. In addition, there are 8 apartments and 7 condos.
Where can I stay if I'm traveling to Chestertown with my kids?
Parents traveling with children may want to consider Three Bears, Immaculate 2 Bed/2.5 bath suite, Heat/ AC & Washer/dryer.
Where should I stay in Chestertown for a vacation with my partner?
Friends Lake Inn and The Fern Lodge are great options for a romantic getaway.
Where should I stay in Chestertown if I want a luxury hotel?
An option for a luxury stay is Friends Lake Inn.
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.

Find out more about Chestertown

Find out more about Chestertown

If you're looking to discover somewhere new, look no further than Chestertown. Whether you're planning to stay for a night or for the week, the area around Chestertown has accommodations to fit every need. Search for hotels in Chestertown with Hotels.com by checking our online map. Our map displays the areas and neighborhoods around all Chestertown hotels so you can see how close you are from landmarks and attractions, and then refine your search within the larger area. The best Chestertown hotel deals are here with our lowest price guarantee.