Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Feb 23 - Feb 24
Tomorrow
Feb 24 - Feb 25
This weekend
Feb 27 - Mar 1
Next weekend
Mar 6 - Mar 8

Where to stay in Chestertown?

Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn
Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (102 reviews)
The price is $223
$248 total
includes taxes & fees
Feb 25 - Feb 26
Friends Lake Inn
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 price is $495
$549 total
includes taxes & fees
Feb 26 - Feb 27
The Fern Lodge
Exterior
Llama House ADK
Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (34 reviews)
  • cleanliness
    Cozy lodge near Gore Mountain, with free WiFi and hiking trails to explore.
The price is $145
$161 total
includes taxes & fees
Feb 25 - Feb 26
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 $1,074
$1,420 total
includes taxes & fees
Feb 25 - Feb 26
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Premium Room | Premium bedding, down comforters, individually decorated
The Alpine Lodge
The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (668 reviews)
The price is $158
$187 total
includes taxes & fees
Mar 26 - Mar 27
The Alpine Lodge
Restaurant
North Creek Lodge at Gore Mountain
North Creek Lodge at Gore Mountain
3.0 star property
North Creek
7.8 out of 10, Good, (434 reviews)
  • cleanliness
    Slope-side convenience meets mountain charm at this cozy North Creek lodge with free perks.
The price is $205
$227 total
includes taxes & fees
Feb 25 - Feb 26
North Creek Lodge at Gore Mountain
Front of property
Gore Mountain Lodge
Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (213 reviews)
The price is $229
$254 total
includes taxes & fees
Mar 10 - Mar 11
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
3.0 star property
Olmstedville
  • cleanliness
    Experience the tranquility of a golf-adjacent home in Olmstedville with hiking trails.
The price is $254
$845 total
includes taxes & fees
Feb 25 - Feb 26
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, (1,005 reviews)
  • cleanliness
    Downtown Lake George getaway with free breakfast and easy access to outdoor fun.
The price is $71
$78 total
includes taxes & fees
Feb 25 - Feb 26
Super 8 by Wyndham Lake George/Warrensburg Area
Premium Chalet, Multiple Beds | Exterior
Lodge at Schroon Lake
Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (432 reviews)
  • cleanliness
    Rustic lakeside retreat with private beach, indoor pool, and marina access.
The price is $145
$197 total
includes taxes & fees
Mar 19 - Mar 20
Lodge at Schroon Lake
Basic Cabin | Private kitchen | Fridge, microwave, coffee/tea maker, electric kettle
Maple Leaf Motel
Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (561 reviews)
  • cleanliness
    Cozy lakeside motel with a seasonal pool and golf course for outdoor enthusiasts.
The price is $119
$134 total
includes taxes & fees
Feb 25 - Feb 26
Maple Leaf Motel
Front of property
Silver Bay YMCA Inn and Conference Center
Silver Bay YMCA Inn and Conference Center
2.0 star property
Silver Bay
8.8 out of 10, Excellent, (139 reviews)
  • cleanliness
    Lakeside tranquility at this serene YMCA inn with fitness center, dining, and beach.
The price is $104
$115 total
includes taxes & fees
Feb 25 - Feb 26
Silver Bay YMCA Inn and Conference Center
Indoor/outdoor pool
Lodges At Cresthaven
Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (557 reviews)
  • cleanliness
    Experience Lake George's charm at this lodge just 15 minutes from Six Flags.
The price is $154
$171 total
includes taxes & fees
Feb 25 - Feb 26
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 $239
$340 total
includes taxes & fees
Feb 25 - Feb 26
Sun Castle Resort
Garden
Pinebrook Motel
Pinebrook Motel
2.0 star property
Lake George
7.4 out of 10, Good, (188 reviews)
  • cleanliness
    Close to Lake George and Six Flags, enjoy a refreshing pool after adventure.
The price is $57
$63 total
includes taxes & fees
Mar 8 - Mar 9
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, (246 reviews)
  • cleanliness
    Relax at this lakeside motel with a seasonal pool and private beach access.
The price is $81
$173 total
includes taxes & fees
Mar 2 - Mar 3
Sundowner on Lake George
Premium bedding, desk, laptop workspace, blackout drapes
Courtyard by Marriott Lake George
Courtyard by Marriott Lake George
3.0 star property
Lake George
9.2 out of 10, Wonderful, (1,004 reviews)
  • cleanliness
    Relax by Lake George with an indoor pool, on-site dining, and convenient amenities.
The price is $112
$124 total
includes taxes & fees
Feb 26 - Feb 27
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 $155
$255 total
includes taxes & fees
Mar 26 - Mar 27
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, (740 reviews)
  • cleanliness
    Walk steps from pristine waters to a welcoming lakefront escape with a rooftop bar.
The price is $214
$263 total
includes taxes & fees
Mar 1 - Mar 2
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, (108 reviews)
  • cleanliness
    Unwind just minutes from Lake George with premium bedding and attentive service.
The price is $112
$124 total
includes taxes & fees
Feb 25 - Feb 26
The Inn of 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 February
Currently viewing crowd sizes and weather for February.
Typical weather for Chestertown
February
High -1°C / low -10°C. Snow likely.
View properties in February
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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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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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July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
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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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September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
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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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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.
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January, no crowd data, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
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

Crystal waters of Loon Lake reflect the Adirondack Mountains, creating a paddler's paradise in upstate New York. Bring your own picnic and rent a kayak to spot the lake's namesake birds calling across the water.
See properties

Friends Lake

This private Adirondack lake offers pristine waters and tranquil surroundings for swimming, fishing, and kayaking. Access is limited to guests of lakeside accommodations, ensuring a peaceful retreat from crowds.
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
"Staff was amazing, breakfast great, and the room was so clean. We only had one problem and that was with another guest who was rude. So i would stay there again. "
Desiree 2-night trip
Posted 16 hours ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Frequently asked questions

What accommodations do travelers like in Chestertown?
Guests like The Fern Lodge, HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles! and North Creek Lodge at Gore Mountain.
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 59 vacation homes. You can also consider one of the 5 apartments or 19 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.