Photo by Julie Miller

Chestertown Hotels

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Check prices for these dates

Tonight
20 Jan - 21 Jan
Tomorrow
21 Jan - 22 Jan
This weekend
23 Jan - 25 Jan
Next weekend
30 Jan - 1 Feb

Where to stay in Chestertown?

Lake view
The Fern Lodge
The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (52 reviews)
  • cleanliness
    Woodland retreat near Adirondack lakes with enchanting private beach and dining.
The Fern Lodge
Exterior
Llama House ADK
Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (33 reviews)
  • cleanliness
    Cosy lodge near Gore Mountain, with free WiFi and hiking trails to explore.
The price is S$191
includes taxes & fees
4 Feb - 5 Feb
Llama House ADK
Exterior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
3.0 star property
Bolton Landing
9.8 out of 10, Exceptional, (17 reviews)
The price is S$1,717
includes taxes & fees
29 Jan - 30 Jan
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Premium bedding, down duvets, individually decorated
The Alpine Lodge
The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (666 reviews)
The price is S$255
includes taxes & fees
22 Jan - 23 Jan
The Alpine Lodge
Restaurant
North Creek Lodge at Gore Mountain
North Creek Lodge at Gore Mountain
3.0 star property
North Creek
8.0 out of 10, Very good, (415 reviews)
  • cleanliness
    Slope-side convenience meets mountain charm at this cosy North Creek lodge with free perks.
The price is S$263
includes taxes & fees
5 Feb - 6 Feb
North Creek Lodge at Gore Mountain
Lunch, dinner served; German cuisine, garden views
Gore Mountain Lodge
Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (212 reviews)
Gore Mountain Lodge
Exterior
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
Olmstedville
  • cleanliness
    Experience the tranquility of a golf-adjacent home in Olmstedville with hiking trails.
The price is S$1,082
includes taxes & fees
22 Jan - 23 Jan
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
Exterior
Super 8 by Wyndham Lake George/Warrensburg Area
Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
Lake George
8.8 out of 10, Excellent, (1,001 reviews)
  • cleanliness
    City centre Lake George getaway with free breakfast and easy access to outdoor fun.
The price is S$97
includes taxes & fees
28 Jan - 29 Jan
Super 8 by Wyndham Lake George/Warrensburg Area
Exterior
Lodge at Schroon Lake
Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (423 reviews)
  • cleanliness
    Rustic lakeside retreat with private beach, indoor pool, and marina access.
The price is S$238
includes taxes & fees
22 Jan - 23 Jan
Lodge at Schroon Lake
Private kitchen
Maple Leaf Motel
Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (552 reviews)
  • cleanliness
    Cosy lakeside motel with a seasonal pool and golf course for outdoor enthusiasts.
The price is S$155
includes taxes & fees
19 Feb - 20 Feb
Maple Leaf Motel
Front of property
Silver Bay YMCA Inn and Conference Center
Silver Bay YMCA Inn and Conference Center
3.0 star property
Silver Bay
8.8 out of 10, Excellent, (138 reviews)
  • cleanliness
    Lakeside tranquility at this serene YMCA inn with fitness centre, dining, and beach.
The price is S$127
includes taxes & fees
22 Jan - 23 Jan
Silver Bay YMCA Inn and Conference Center
Terrace/patio
Lodges At Cresthaven
Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (551 reviews)
  • cleanliness
    Experience Lake George's charm at this lodge just 15 minutes from Six Flags.
Lodges At Cresthaven
Flat-screen TV, DVD player
Sun Castle Resort
Sun Castle Resort
3.5 star property
Lake George
9.0 out of 10, Wonderful, (62 reviews)
The price is S$506
includes taxes & fees
22 Jan - 23 Jan
Sun Castle Resort
Garden
Pinebrook Motel
Pinebrook Motel
2.0 star property
Lake George
7.4 out of 10, Good, (187 reviews)
  • cleanliness
    Close to Lake George and Six Flags, enjoy a refreshing pool after adventure.
The price is S$96
includes taxes & fees
22 Jan - 23 Jan
Pinebrook Motel
Private beach, kayaking, rowing
Sundowner on Lake George
Sundowner on Lake George
2.5 star property
Lake George
7.6 out of 10, Good, (245 reviews)
  • cleanliness
    Relax at this lakeside motel with a seasonal pool and private beach access.
The price is S$218
includes taxes & fees
26 Jan - 27 Jan
Sundowner on Lake George
Premium bedding, desk, laptop workspace, blackout curtains
Courtyard by Marriott Lake George
Courtyard by Marriott Lake George
3.0 star property
Lake George
9.2 out of 10, Wonderful, (1,000 reviews)
  • cleanliness
    Relax by Lake George with an indoor pool, on-site dining, and convenient amenities.
The price is S$177
includes taxes & fees
4 Feb - 5 Feb
Courtyard by Marriott Lake George
Property entrance
Lake Haven Motel
Lake Haven Motel
2.5 star property
Lake George
7.4 out of 10, Good, (110 reviews)
  • cleanliness
    Stay lakeside at this relaxing motel, minutes from Six Flags Great Escape.
The price is S$380
includes taxes & fees
22 Jan - 23 Jan
Lake Haven Motel
Private beach, sun-loungers, kayaking
Surfside On The Lake
Surfside On The Lake
2.5 star property
Lake George
8.0 out of 10, Very good, (738 reviews)
  • cleanliness
    Walk steps from pristine waters to a welcoming lakefront escape with a rooftop bar.
Surfside On The Lake
Bar (on property)
The Inn of Lake George
The Inn of Lake George
2.5 star property
Lake George
9.6 out of 10, Exceptional, (106 reviews)
  • cleanliness
    Unwind just minutes from Lake George with premium bedding and attentive service.
The Inn of Lake George
Desk, free WiFi, bed sheets
Howard Johnson by Wyndham Lake George
Howard Johnson by Wyndham Lake George
2.0 star property
Lake George
8.0 out of 10, Very good, (1,000 reviews)
  • cleanliness
    Central to Lake George attractions with a relaxing pool to complete your day.
The price is S$101
includes taxes & fees
16 Feb - 17 Feb
Howard Johnson by Wyndham Lake George
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 traveller single night rates
View properties in January
Currently viewing crowd sizes and weather for January.
Typical weather for Chestertown
January
High -2°C / low -11°C. Snow likely.
View properties in January
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January, no crowd data, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature -1 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 11 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
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19°
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May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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27°
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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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26°
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August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
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22°
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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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14°
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October, no crowd data, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
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7°
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November, no crowd data, average high temperature 7 degrees Celsius, average low temperature -1 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
Monthly weather averages (˚C)

Top neighbourhoods in Chestertown

Chester Shores

Chestertown's Chester Shores neighbourhood 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?
See properties

Friends Lake

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

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

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent
"Surprised by the bag of water and snacks provided at check in. "
David 1-night trip
Posted 7 days ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Frequently asked questions

How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from S$96 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 S$96 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 57 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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