Photo by Julie Miller

Hotels in Chestertown

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Where to stay in Chestertown?

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
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 CNY1,009
CNY1,120 total
includes taxes & fees
Feb 10 - Feb 11
Llama House ADK
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 CNY7,449
CNY9,846 total
includes taxes & fees
Feb 10 - Feb 11
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
The Alpine Lodge
The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (666 reviews)
The Alpine Lodge
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, (420 reviews)
  • cleanliness
    Slope-side convenience meets mountain charm at this cozy North Creek lodge with free perks.
The price is CNY1,086
CNY1,206 total
includes taxes & fees
Feb 10 - Feb 11
North Creek Lodge at Gore Mountain
Gore Mountain Lodge
Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (213 reviews)
Gore Mountain Lodge
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 CNY1,763
CNY5,862 total
includes taxes & fees
Feb 10 - Feb 11
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
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, (1,003 reviews)
  • cleanliness
    Downtown Lake George getaway with free breakfast and easy access to outdoor fun.
The price is CNY507
CNY563 total
includes taxes & fees
Mar 3 - Mar 4
Super 8 by Wyndham Lake George/Warrensburg Area
Lodge at Schroon Lake
Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (426 reviews)
  • cleanliness
    Rustic lakeside retreat with private beach, indoor pool, and marina access.
Lodge at Schroon Lake
Maple Leaf Motel
Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (555 reviews)
  • cleanliness
    Cozy lakeside motel with a seasonal pool and golf course for outdoor enthusiasts.
The price is CNY743
CNY839 total
includes taxes & fees
Feb 10 - Feb 11
Maple Leaf Motel
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, (138 reviews)
  • cleanliness
    Lakeside tranquility at this serene YMCA inn with fitness center, dining, and beach.
The price is CNY680
CNY755 total
includes taxes & fees
Feb 10 - Feb 11
Silver Bay YMCA Inn and Conference Center
Lodges At Cresthaven
Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (555 reviews)
  • cleanliness
    Experience Lake George's charm at this lodge just 15 minutes from Six Flags.
The price is CNY1,131
CNY1,255 total
includes taxes & fees
Feb 22 - Feb 23
Lodges At Cresthaven
Sun Castle Resort
Sun Castle Resort
3.5 star property
Lake George
9.0 out of 10, Wonderful, (62 reviews)
The price is CNY1,656
CNY2,729 total
includes taxes & fees
Feb 10 - Feb 11
Sun Castle Resort
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 CNY395
CNY438 total
includes taxes & fees
Mar 8 - Mar 9
Pinebrook Motel
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 CNY539
CNY1,176 total
includes taxes & fees
Mar 2 - Mar 3
Sundowner on Lake George
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 CNY967
CNY1,651 total
includes taxes & fees
Feb 12 - Feb 13
Lake Haven Motel
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)
  • cleanliness
    Relax by Lake George with an indoor pool, on-site dining, and convenient amenities.
The price is CNY777
CNY862 total
includes taxes & fees
Feb 22 - Feb 23
Courtyard by Marriott Lake George
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.
Surfside On The Lake
The Inn of Lake George
The Inn of Lake George
2.5 star property
Lake George
9.6 out of 10, Exceptional, (107 reviews)
  • cleanliness
    Unwind just minutes from Lake George with premium bedding and attentive service.
The Inn of 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, (1,003 reviews)
  • cleanliness
    Central to Lake George attractions with a relaxing pool to complete your day.
The price is CNY418
CNY464 total
includes taxes & fees
Feb 17 - Feb 18
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.

When is the best time to visit Chestertown?

Our prices for hotels in Chestertown are cheapest in June
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

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.

A winter scene
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 from CNY438 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 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.
Can I book Chestertown hotels with free cancellation?
In order to book a refundable Chestertown hotel, simply filter hotels by "Property cancellation options" and select "Fully refundable property". Most 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 vacation. Our travelers love Friends Lake Inn, a hotel with a restaurant as well as in-room 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 "Traveler 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 driving, a great Chestertown hotel with free parking is a bonus. Our travelers' favorites include:
What are some popular hotels in central Chestertown?
If you're looking for hotels in central Chestertown, check out Friends Lake Inn. Travelers love Friends Lake Inn for its location, as well as the restaurant, bar/lounge and couples/private dining this hotel offers. Chester Shores is a central neighborhood for your Chestertown vacation.
What accommodations do travelers like in Chestertown?
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 58 vacation homes. You can also consider one of the 7 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.