Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Jan 9 - Jan 10
Tomorrow
Jan 10 - Jan 11
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Where to stay in Chestertown?

Lake view
The Fern Lodge
The Fern Lodge
The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (52 reviews)
The price is $478
$531 total
includes taxes & fees
Jan 11 - Jan 12
The Fern Lodge
Exterior
Llama House ADK
Llama House ADK
Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (33 reviews)
The price is $145
$161 total
includes taxes & fees
Jan 12 - Jan 13
Llama House ADK
Exterior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
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, (16 reviews)
The price is $1,074
$1,486 total
includes taxes & fees
Jan 10 - Jan 11
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Premium Room | Premium bedding, down comforters, individually decorated
The Alpine Lodge
The Alpine Lodge
The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (664 reviews)
The price is $161
$189 total
includes taxes & fees
Jan 11 - Jan 12
The Alpine Lodge
Restaurant
North Creek Lodge at Gore Mountain
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, (411 reviews)
The price is $205
$227 total
includes taxes & fees
Jan 11 - Jan 12
North Creek Lodge at Gore Mountain
Lunch, dinner served; German cuisine, garden views
Gore Mountain Lodge
Gore Mountain Lodge
Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (212 reviews)
The price is $229
$254 total
includes taxes & fees
Jan 22 - Jan 23
Gore Mountain Lodge
House, 5 Bedrooms | 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
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
Olmstedville
The price is $254
$845 total
includes taxes & fees
Jan 11 - Jan 12
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
Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
Lake George
8.8 out of 10, Excellent, (1,001 reviews)
The price is $74
$82 total
includes taxes & fees
Jan 25 - Jan 26
Super 8 by Wyndham Lake George/Warrensburg Area
Premium Chalet, Multiple Beds | Exterior
Lodge at Schroon Lake
Lodge at Schroon Lake
Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (421 reviews)
The price is $127
$176 total
includes taxes & fees
Jan 10 - Jan 11
Lodge at Schroon Lake
Basic Cabin | Private kitchen | Fridge, microwave, coffee/tea maker, electric kettle
Maple Leaf Motel
Maple Leaf Motel
Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (551 reviews)
The price is $119
$134 total
includes taxes & fees
Jan 10 - Jan 11
Maple Leaf Motel
Front of property
Silver Bay YMCA Inn and Conference Center
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, (137 reviews)
The price is $120
$133 total
includes taxes & fees
Jan 10 - Jan 11
Silver Bay YMCA Inn and Conference Center
Terrace/patio
Lodges At Cresthaven
Lodges At Cresthaven
Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (549 reviews)
The price is $154
$171 total
includes taxes & fees
Jan 11 - Jan 12
Lodges At Cresthaven
Flat-screen TV, DVD player
Sun Castle Resort
Sun Castle Resort
Sun Castle Resort
3.5 star property
Lake George
9.0 out of 10, Wonderful, (62 reviews)
The price is $239
$394 total
includes taxes & fees
Jan 11 - Jan 12
Sun Castle Resort
Garden
Pinebrook Motel
Pinebrook Motel
Pinebrook Motel
2.0 star property
Lake George
7.4 out of 10, Good, (187 reviews)
The price is $67
$75 total
includes taxes & fees
Jan 11 - Jan 12
Pinebrook Motel
Private beach, kayaking, rowing
Sundowner on Lake George
Sundowner on Lake George
Sundowner on Lake George
2.5 star property
Lake George
7.6 out of 10, Good, (245 reviews)
The price is $81
$173 total
includes taxes & fees
Jan 12 - Jan 13
Sundowner on Lake George
Premium bedding, desk, laptop workspace, blackout drapes
Courtyard by Marriott Lake George
Courtyard by Marriott Lake George
Courtyard by Marriott Lake George
3.0 star property
Lake George
9.2 out of 10, Wonderful, (1,002 reviews)
The price is $109
$121 total
includes taxes & fees
Feb 2 - Feb 3
Courtyard by Marriott Lake George
Property entrance
Lake Haven Motel
Lake Haven Motel
Lake Haven Motel
2.5 star property
Lake George
7.4 out of 10, Good, (110 reviews)
The price is $211
$317 total
includes taxes & fees
Feb 8 - Feb 9
Lake Haven Motel
Private beach, sun loungers, kayaking
Surfside On The Lake
Surfside On The Lake
Surfside On The Lake
2.5 star property
Lake George
8.0 out of 10, Very Good, (738 reviews)
The price is $193
$239 total
includes taxes & fees
Feb 1 - Feb 2
Surfside On The Lake
Bar (on property)
The Inn of Lake George
The Inn of Lake George
The Inn of Lake George
2.5 star property
Lake George
9.6 out of 10, Exceptional, (106 reviews)
The price is $112
$124 total
includes taxes & fees
Jan 12 - Jan 13
The Inn of Lake George
Room, 2 Queen Beds, Non Smoking | Desk, free WiFi, bed sheets
Howard Johnson by Wyndham Lake George
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)
The price is $99
$110 total
includes taxes & fees
Jan 31 - Feb 1
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 September
Price trends for hotels in Chestertown
Pricing is based on two traveler 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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4°
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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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11°
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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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23°
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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.
-1°
1°
ac_unit
December, no crowd data, average high temperature 1 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
Monthly weather averages (˚C)

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.
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

The Queensbury Hotel

The Queensbury Hotel

10/10 Excellent
"The room was clean, beautiful and full of old school charm. We loved the holiday decorations in the lobby. "
Jennifer 1-night trip
Posted 3 days ago
The Queensbury Hotel

Frequently asked questions

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 57 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.