Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Feb 24 - Feb 25
Tomorrow
Feb 25 - Feb 26
This weekend
Feb 28 - Mar 2
Next weekend
Mar 7 - Mar 9

Where to stay in Chestertown?

Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
9.0 out of 10, Wonderful, (87)
The price is $248
includes taxes & fees
$223 per night
Feb 25 - Feb 26
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
The price is $659
includes taxes & fees
$593 per night
Mar 4 - Mar 5
The Fern Lodge
Llama House ADK
Front of property

Llama House ADK

2.5 star property
9.0 out of 10, Wonderful, (23)
The price is $147
includes taxes & fees
$132 per night
Feb 25 - Feb 26
Llama House ADK
Gore Mountain Lodge
Lunch, dinner served; German cuisine, garden views

Gore Mountain Lodge

2.0 star property
9.2 out of 10, Wonderful, (196)
The price is $254
includes taxes & fees
$229 per night
Mar 10 - Mar 11
Gore Mountain 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.
data_trends

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
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
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
Currently viewing crowd sizes and weather for February.

February

trending_flatModerate crowds
High 30°F / low 14°F. Snow likely.
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°
80°
weather_sun
July, High crowds, average high temperature 80 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
59°
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.
41°
44°
weather_partly_sunny
November, Low crowds, average high temperature 44 degrees Fahrenheit, average low temperature 29 degrees Fahrenheit. Partly sunny.
29°
33°
ac_unit
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°
Monthly weather averages (˚F)
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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

Loon Lake

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

See properties in Loon Lake
Loon Lake

Loon Lake Beach

If you can't wait to get to the beach, you might enjoy a trip to Loon Lake Beach located 2 mi (3.3 km) from central Chestertown.

See properties in Loon Lake Beach
Loon Lake Beach

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.
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.