Photo by Julie Miller

Hotels in Chestertown

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Check prices for these dates

Tonight
Jan 16 - Jan 17
Tomorrow
Jan 17 - Jan 18
This weekend
Jan 16 - Jan 18
Next weekend
Jan 23 - Jan 25

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.
$478 nightly
The price is $531
Jan 19 - Jan 20
Total with taxes and fees
The Fern Lodge
Exterior
Llama House ADK
Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (33 reviews)
  • cleanliness
    Cozy lodge near Gore Mountain, with free WiFi and hiking trails to explore.
$138 nightly
The price is $154
Feb 2 - Feb 3
Total with taxes and fees
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, (16 reviews)
$1,236 nightly
The price is $1,373
Jan 19 - Jan 20
Total with taxes and fees
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, (666 reviews)
$179 nightly
The price is $198
Jan 20 - Jan 21
Total with taxes and fees
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, (412 reviews)
  • cleanliness
    Slope-side convenience meets mountain charm at this cozy North Creek lodge with free perks.
$205 nightly
The price is $227
Jan 19 - Jan 20
Total with taxes and fees
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)
$289 nightly
The price is $321
Jan 26 - Jan 27
Total with taxes and fees
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.
$739 nightly
The price is $835
Jan 22 - Jan 23
Total with taxes and fees
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, (1,000 reviews)
  • cleanliness
    Downtown Lake George getaway with free breakfast and easy access to outdoor fun.
$66 nightly
The price is $74
Jan 27 - Jan 28
Total with taxes and fees
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, (422 reviews)
  • cleanliness
    Rustic lakeside retreat with private beach, indoor pool, and marina access.
$164 nightly
The price is $185
Jan 22 - Jan 23
Total with taxes and fees
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, (552 reviews)
  • cleanliness
    Cozy lakeside motel with a seasonal pool and golf course for outdoor enthusiasts.
$119 nightly
The price is $134
Jan 18 - Jan 19
Total with taxes and fees
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 center, dining, and beach.
$99 nightly
The price is $110
Jan 18 - Jan 19
Total with taxes and fees
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, (549 reviews)
  • cleanliness
    Experience Lake George's charm at this lodge just 15 minutes from Six Flags.
$154 nightly
The price is $171
Jan 19 - Jan 20
Total with taxes and fees
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)
$367 nightly
The price is $394
Jan 19 - Jan 20
Total with taxes and fees
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.
$67 nightly
The price is $75
Jan 18 - Jan 19
Total with taxes and fees
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.
$156 nightly
The price is $173
Jan 19 - Jan 20
Total with taxes and fees
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, (1,000 reviews)
  • cleanliness
    Relax by Lake George with an indoor pool, on-site dining, and convenient amenities.
$112 nightly
The price is $124
Jan 19 - Jan 20
Total with taxes and fees
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.
$271 nightly
The price is $301
Jan 19 - Jan 20
Total with taxes and fees
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.
$215 nightly
The price is $239
Feb 1 - Feb 2
Total with taxes and fees
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.
$113 nightly
The price is $125
Jan 21 - Jan 22
Total with taxes and fees
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
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.
$75 nightly
The price is $83
Feb 16 - Feb 17
Total with taxes and fees
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 traveler single night rates
View properties in January
Currently viewing crowd sizes and weather for January.
Typical weather for Chestertown
January
High 28°F / low 13°F. Snow likely.
View properties in January
28°
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January, no crowd data, average high temperature 28 degrees Fahrenheit, average low temperature 13 degrees Fahrenheit. Snow likely.
13°
30°
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February, no crowd data, average high temperature 30 degrees Fahrenheit, average low temperature 14 degrees Fahrenheit. Snow likely.
14°
39°
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March, no crowd data, average high temperature 39 degrees Fahrenheit, average low temperature 22 degrees Fahrenheit. Snow likely.
22°
52°
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April, no crowd data, average high temperature 52 degrees Fahrenheit, average low temperature 33 degrees Fahrenheit. Cloudy most days.
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67°
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May, no crowd data, average high temperature 67 degrees Fahrenheit, average low temperature 45 degrees Fahrenheit. Sunny most days.
45°
74°
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June, no crowd data, average high temperature 74 degrees Fahrenheit, average low temperature 53 degrees Fahrenheit. Sunny most days.
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80°
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July, no crowd data, average high temperature 80 degrees Fahrenheit, average low temperature 59 degrees Fahrenheit. Sunny most days.
59°
78°
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August, no crowd data, average high temperature 78 degrees Fahrenheit, average low temperature 58 degrees Fahrenheit. Sunny most days.
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71°
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September, no crowd data, average high temperature 71 degrees Fahrenheit, average low temperature 51 degrees Fahrenheit. Sunny most days.
51°
57°
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October, no crowd data, average high temperature 57 degrees Fahrenheit, average low temperature 41 degrees Fahrenheit. Cloudy most days.
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44°
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November, no crowd data, average high temperature 44 degrees Fahrenheit, average low temperature 29 degrees Fahrenheit. Partly sunny.
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33°
ac_unit
December, no crowd data, average high temperature 33 degrees Fahrenheit, average low temperature 22 degrees Fahrenheit. Snow likely.
22°
Monthly weather averages (˚F)

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
"great place "
Scott 1-night trip
Posted 3 days ago
The Queensbury Hotel

Frequently asked questions

How much does a hotel room cost in Chestertown?
You can find top hotels in Chestertown from $74 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 private picnics this hotel offers. Chester Shores is a central neighborhood for your Chestertown vacation.
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.

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