Photo by Julie Miller

Hotels in Chestertown

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Where to stay in Chestertown?

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.

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 traveller single night rates
View properties in December
Currently viewing crowd sizes and weather for December.
Typical weather for Chestertown
December
Moderate crowds
High 1°C / low -6°C. Snow likely.
View properties in December
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December, Moderate crowds, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
-2°
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January, Low crowds, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
-1°
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February, Moderate crowds, average high temperature -1 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
-10°
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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.
19°
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May, Low crowds, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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°
weather_cloudy
October, High crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
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November, Low crowds, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
-1°
Monthly weather averages (˚C)

Top neighbourhoods in Chestertown

Chester Shores

Chestertown's Chester Shores neighbourhood offers attractions, including Loon Lake.

Top landmarks in Chestertown

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.

A winter scene
Photo by Julie Miller
Open Photo by Julie Miller

Check out reviews of Chestertown hotels guests love

Check out reviews of Chestertown hotels guests love

Frequently asked questions

How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from AU$112 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".
How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from AU$112 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?
Discover great deals on Chestertown hotel stays with Hotels.com. Take a look at hotel prices mid-week or during the low season as to find those off-peak deals. And make sure to check out our last-minute deals on Chestertown hotels.
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 travellers love Friends Lake Inn, a hotel with a restaurant as well as 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 "Traveller 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 travellers' favourites include:
Can I book a refundable accommodation option in Chestertown?
If you want the flexibility to change your plans to Chestertown, most hotels offer refundable* rates that you can book. You can see this accommodation 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 holiday rental instead of a hotel?
If you want to find a good alternative to a hotel, review our selection of 58 holiday 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 temperature of 18°C. January and February are the chilliest months, when the average temperature is -4°C. 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, our Price Guarantee ensures that you always get the lowest price, and you can earn rewards on every booking.

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