Photo by Julie Miller

Hotels in Chestertown

Free cancellation options if plans change

Earn rewards on every night you stay

Save more with Member Prices

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.
The price is $478
$531 total
includes taxes & fees
Jan 19 - Jan 20
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.
The price is $145
$161 total
includes taxes & fees
Jan 29 - Jan 30
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)
The price is $1,074
$1,420 total
includes taxes & fees
Jan 18 - Jan 19
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)
The price is $169
$198 total
includes taxes & fees
Jan 20 - Jan 21
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.
The price is $205
$227 total
includes taxes & fees
Jan 19 - Jan 20
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)
The price is $289
$321 total
includes taxes & fees
Jan 26 - Jan 27
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
Jan 20 - Jan 21
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.
The price is $66
$74 total
includes taxes & fees
Jan 27 - Jan 28
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, (423 reviews)
  • cleanliness
    Rustic lakeside retreat with private beach, indoor pool, and marina access.
The price is $135
$185 total
includes taxes & fees
Jan 22 - Jan 23
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.
The price is $119
$134 total
includes taxes & fees
Jan 18 - Jan 19
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.
The price is $99
$110 total
includes taxes & fees
Jan 18 - Jan 19
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.
The price is $154
$171 total
includes taxes & fees
Jan 19 - Jan 20
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
$394 total
includes taxes & fees
Jan 19 - Jan 20
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.
The price is $67
$75 total
includes taxes & fees
Jan 18 - Jan 19
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.
The price is $81
$173 total
includes taxes & fees
Jan 19 - Jan 20
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, (1,001 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
Jan 19 - Jan 20
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 $196
$301 total
includes taxes & fees
Jan 19 - Jan 20
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.
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
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.
The price is $113
$125 total
includes taxes & fees
Jan 21 - Jan 22
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.
The price is $75
$83 total
includes taxes & fees
Feb 16 - Feb 17
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.
View all properties

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
-2°
ac_unit
January, no crowd data, average high temperature -2 degrees Celsius, average low temperature -11 degrees Celsius. Snow likely.
-11°
-1°
ac_unit
February, no crowd data, average high temperature -1 degrees Celsius, average low temperature -10 degrees Celsius. Snow likely.
-10°
4°
ac_unit
March, no crowd data, average high temperature 4 degrees Celsius, average low temperature -6 degrees Celsius. Snow likely.
-6°
11°
weather_cloudy
April, no crowd data, average high temperature 11 degrees Celsius, average low temperature 1 degrees Celsius. Cloudy most days.
1°
19°
weather_sun
May, no crowd data, average high temperature 19 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
7°
23°
weather_sun
June, no crowd data, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
12°
27°
weather_sun
July, no crowd data, average high temperature 27 degrees Celsius, average low temperature 15 degrees Celsius. Sunny most days.
15°
26°
weather_sun
August, no crowd data, average high temperature 26 degrees Celsius, average low temperature 14 degrees Celsius. Sunny most days.
14°
22°
weather_sun
September, no crowd data, average high temperature 22 degrees Celsius, average low temperature 11 degrees Celsius. Sunny most days.
11°
14°
weather_cloudy
October, no crowd data, average high temperature 14 degrees Celsius, average low temperature 5 degrees Celsius. Cloudy most days.
5°
7°
weather_partly_sunny
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
"great place "
Scott 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.