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)
$599 nightly
The price is $665
Nov 28 - Nov 29
Total with taxes and fees
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 October
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 44°F / low 29°F. Partly sunny.
View properties in November
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°
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April, Moderate crowds, average high temperature 52 degrees Fahrenheit, average low temperature 33 degrees Fahrenheit. Cloudy most days.
33°
67°
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May, Low crowds, average high temperature 67 degrees Fahrenheit, average low temperature 45 degrees Fahrenheit. Sunny most days.
45°
74°
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June, High crowds, average high temperature 74 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
53°
80°
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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°
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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°
Monthly weather averages (˚F)

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 16 hours ago
The Queensbury Hotel

Frequently asked questions

How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from $75 with options to suit your budget and needs. To find an affordable hotel in Chestertown that meets all of your requirements, just apply filters on Hotels.com, and sort hotels by "Price: low to high". If you're a member, don't forget to sign in to your account to unlock more savings.
How can I find deals and earn rewards at Chestertown hotels?
Members can save up to 20% on select hotels in Chestertown. Plus, Silver, Gold and Platinum members earn extra rewards on VIP Access bookings, making each stay even more rewarding.

Can I book Chestertown hotels with free cancellation?
To book a refundable Chestertown hotel on Hotels.com, just filter hotels by "Property cancellation options" and select "Fully refundable property". Many hotels offer free cancellation, so you can receive a refund if you need to cancel. Some hotels do require cancelling more than 24 hours before check-in, so double-check your booking beforehand.
What are some of the best hotels in Chestertown for couples?
Choose a top-rated Chestertown romantic hotel and enjoy your couple's getaway. Our travelers love Friends Lake Inn, a hotel with a restaurant as well as in-room champagne service. Another romantic hotel with top reviews is The Fern Lodge. This bed & breakfast offers a private hot tub and an in-room fireplace for a perfect stay. Discover more hotels in Chestertown on Hotels.com for couples by using the "Traveler experience" filter in your search and selecting "Adults only" or "Romantic".
What are some of the best Chestertown hotels with free parking?
If you're arriving by car, choosing a great Chestertown hotel with free parking is a plus. Our travelers' favorites include:
What are some popular hotels in central Chestertown?
If you're looking for hotels in central Chestertown, check out Friends Lake Inn. Travelers love Friends Lake Inn for its location, as well as the restaurant, bar/lounge and couples/private dining this hotel offers. Chester Shores is a central neighborhood for your Chestertown vacation.
Are all taxes and fees included in the Chestertown hotel prices shown on Hotels.com?
Hotels.com provides upfront pricing so you can relax knowing you won't be met with surprise additional fees or taxes when you're ready to confirm your booking. From the time you start your search on Hotels.com, the price you see is what you pay. This makes it much easier to compare properties and secure our best deal for your next getaway.
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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