Photo by Julie Miller

Chestertown Hotels

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Check prices for these dates

Tonight
28 Oct - 29 Oct
Tomorrow
29 Oct - 30 Oct
This weekend
31 Oct - 2 Nov
Next weekend
7 Nov - 9 Nov

Where to stay in Chestertown?

1 bedroom, premium bedding, individually decorated
Friends Lake Inn
Friends Lake Inn
4.0 star property
8.6 out of 10, Excellent, (102)
The price is S$372
includes taxes & fees
11 Nov - 12 Nov
Friends Lake Inn
Lake view
The Fern Lodge
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (49)
The Fern Lodge
Front of property
Llama House ADK
Llama House ADK
2.5 star property
9.0 out of 10, Wonderful, (30)
Llama House ADK
Interior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3.0 star property
9.8 out of 10, Exceptional, (16)
The price is S$1,927
includes taxes & fees
1 Nov - 2 Nov
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
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 Chestertown are cheapest in October

See average prices and weather for all months
Price trends for hotels in Chestertown
Pricing is based on two traveller single night rates
View properties in October
Currently viewing crowd sizes and weather for October.
Weather forecast for Chestertown
October
High crowds
High 14°C / low 5°C. Cloudy most days.
View properties in October
14°
weather_cloudy
October, High crowds, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
5°
7°
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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°
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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°
4°
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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.
1°
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°
Monthly weather averages (˚C)

Top neighbourhoods in Chestertown

Chester Shores

Chestertown's Chester Shores neighbourhood 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?
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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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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.
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Tripp Pond

Tripp Pond is 3.9 mi (6.3 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
Photo by Julie Miller
Open Photo by Julie Miller

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 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 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?
It's easy to book a refundable Chestertown hotel on Hotels.com. Simply filter hotels by "Property cancellation options" and select "Fully refundable property". The majority of 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?
Stay at a top-rated Chestertown romantic hotel and make the most of your couple's holiday. 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 exploring by car, finding a great Chestertown hotel with free parking is a win. 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 60 holiday homes. In addition, there are 7 apartments and 5 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 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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