Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Feb 22 - Feb 23
Tomorrow
Feb 23 - Feb 24
Next weekend
Feb 27 - Mar 1
In two weeks
Mar 6 - Mar 8

Where to stay in Chestertown?

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 P12,970
P14,397 total
includes taxes & fees
Feb 24 - Feb 25
Friends Lake Inn
Lake view
The Fern Lodge
The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (52 reviews)
Tucked into the forests of Chestertown, this cozy B&B offers a lakeside escape with a private beach. Enjoy complimentary breakfast, unwind in the sauna, or book a relaxing massage. Friends Lake and Loon Lake Beach are nearby for outdoor adventures.
The Fern Lodge
Exterior
Llama House ADK
Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (34 reviews)
Experience the Adirondacks at this charming Wevertown lodge offering complimentary WiFi and parking. Just minutes from Gore Mountain Ski Resort, enjoy nearby hiking trails, kayaking, and mountain biking. A lobby fireplace welcomes you back after outdoor adventures.
The price is P8,459
P9,390 total
includes taxes & fees
Feb 24 - Feb 25
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 P62,461
P82,565 total
includes taxes & fees
Feb 24 - Feb 25
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
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 Alpine Lodge
Front of property
Gore Mountain Lodge
Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (213 reviews)
Gore Mountain 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, (432 reviews)
Warm mountain retreat near Gore Mountain Ski Resort offers free breakfast, WiFi, and parking. After hitting the slopes, unwind at the on-site restaurant or bar. Guests consistently praise the helpful staff and immaculate rooms, with High Pines Glades also nearby.
The price is P10,717
P11,895 total
includes taxes & fees
Mar 8 - Mar 9
North Creek Lodge at Gore Mountain
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
This cozy vacation home sits next to a golf course in Olmstedville, offering free WiFi and Smart TV entertainment. Explore nearby hiking trails, cross-country skiing routes, or visit Minerva Lake and Natural Stone Bridge and Caves.
The price is P14,785
P49,154 total
includes taxes & fees
Feb 24 - Feb 25
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, (1,004 reviews)
Wake up to complimentary breakfast at this conveniently located motel near Warren County Nature Trails. Enjoy free WiFi and parking while exploring nearby Lake George and Six Flags Great Escape. Travelers praise the helpful staff and clean, quiet rooms despite busy seasons.
The price is P4,152
P4,610 total
includes taxes & fees
Feb 24 - Feb 25
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, (431 reviews)
Immersive Adirondack experience at this Schroon Lake gem offering a private beach, full-service marina, and restaurant with bar. After exploring nearby Strand Theater, unwind in the sauna, hot tub, or 24-hour gym while enjoying free WiFi and parking.
Lodge at Schroon Lake
Private kitchen
Maple Leaf Motel
Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (561 reviews)
This charming Schroon Lake motel offers an 18-hole golf course and seasonal outdoor pool. Guests can enjoy snowmobiling, free WiFi, and complimentary parking. Located near Strand Theater and Park Beach with clean rooms that previous guests praise.
The price is P6,229
P7,038 total
includes taxes & fees
Feb 24 - Feb 25
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)
Escape to a peaceful retreat on Lake George with complimentary breakfast, WiFi, and parking. The 24-hour fitness center keeps your routine intact while the restaurant satisfies your appetite. Located near Huletts Landing Marina, this quiet haven earns praise for its attentive staff.
The price is P6,031
P6,694 total
includes taxes & fees
Feb 24 - Feb 25
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)
Escape to this beach lodge on Lake George with easy access to local attractions including Dark Bay and Hearthstone Point Campground. After a workout in the 24-hour fitness center, enjoy the restaurant or unwind at the bar. Free WiFi and parking enhance your stay.
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 P13,888
P19,777 total
includes taxes & fees
Feb 24 - Feb 25
Sun Castle Resort
Garden
Pinebrook Motel
Pinebrook Motel
2.0 star property
Lake George
7.4 out of 10, Good, (188 reviews)
Positioned a short drive from Lake George and Six Flags Great Escape, this motel offers a seasonal outdoor pool for cooling off after exploring. Free WiFi and parking add value, while nearby Lakeside Trail invites nature enthusiasts.
The price is P3,311
P3,676 total
includes taxes & fees
Mar 8 - Mar 9
Pinebrook Motel
Property entrance
Lake Haven Motel
Lake Haven Motel
2.5 star property
Lake George
7.4 out of 10, Good, (110 reviews)
Discover tranquil accommodation at Lake George with a refreshing seasonal outdoor pool and convenient free WiFi and parking. Located just a short drive from Six Flags Great Escape and Lakeside Trail, this motel offers easy access to popular attractions.
The price is P8,852
P14,667 total
includes taxes & fees
Mar 26 - Mar 27
Lake Haven 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)
Escape to Lake George at this beachfront haven with a seasonal outdoor pool and soothing hot tub. Just a short drive from Six Flags Great Escape, enjoy the private beach and free parking while exploring nearby Black Mountain Loop.
The price is P4,522
P9,861 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)
This lakeside hotel combines comfort with adventure, featuring a welcoming bar and 24-hour fitness center. Just minutes from Six Flags Great Escape and Black Mountain Loop, enjoy free WiFi and parking after exploring nearby attractions.
The price is P6,514
P7,230 total
includes taxes & fees
Feb 25 - Feb 26
Courtyard by Marriott Lake George
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)
This charming guesthouse offers complimentary WiFi and parking while placing you near Six Flags Great Escape. Guests consistently praise the helpful staff. Explore nearby Patriot of Lake George Museum or venture to Glens Falls, just 22 minutes away.
The Inn of Lake George
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)
Surfside On The Lake offers direct beach access and panoramic views from its rooftop terrace. Enjoy American cuisine at Club Hamilton, one of 2 restaurants, before exploring Lake George or driving to Six Flags Great Escape. Clean rooms and attentive staff enhance your stay.
Surfside On The Lake
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.
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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
"Cozy hotel and great staff. Stay here every time we come to Glens Falls."
Taylor 3-night trip
Posted 23 hours ago
The Queensbury Hotel

Frequently asked questions

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.

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