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 10 - Jan 11
Tomorrow
Jan 11 - Jan 12
Next weekend
Jan 16 - Jan 18
In two weeks
Jan 23 - Jan 25

Where to stay in Chestertown?

Lake view
The Fern Lodge
The Fern Lodge
The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (52 reviews)
The Fern Lodge
Exterior
Llama House ADK
Llama House ADK
Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (33 reviews)
The price is CNY1,015
CNY1,127 total
includes taxes & fees
Jan 12 - Jan 13
Llama House ADK
Exterior
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
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 CNY7,495
CNY10,372 total
includes taxes & fees
Jan 11 - Jan 12
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
Premium Room | Premium bedding, down comforters, individually decorated
The Alpine Lodge
The Alpine Lodge
The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (664 reviews)
The price is CNY1,121
CNY1,319 total
includes taxes & fees
Jan 19 - Jan 20
The Alpine Lodge
Restaurant
North Creek Lodge at Gore Mountain
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, (411 reviews)
The price is CNY857
CNY952 total
includes taxes & fees
Jan 11 - Jan 12
North Creek Lodge at Gore Mountain
Lunch, dinner served; German cuisine, garden views
Gore Mountain Lodge
Gore Mountain Lodge
Gore Mountain Lodge
2.0 star property
North Creek
9.2 out of 10, Wonderful, (212 reviews)
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
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
3.0 star property
Olmstedville
The price is CNY1,774
CNY5,898 total
includes taxes & fees
Jan 12 - Jan 13
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
Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
Lake George
8.8 out of 10, Excellent, (1,001 reviews)
The price is CNY516
CNY573 total
includes taxes & fees
Jan 25 - Jan 26
Super 8 by Wyndham Lake George/Warrensburg Area
Premium Chalet, Multiple Beds | Exterior
Lodge at Schroon Lake
Lodge at Schroon Lake
Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (421 reviews)
The price is CNY885
CNY1,229 total
includes taxes & fees
Feb 7 - Feb 8
Lodge at Schroon Lake
Basic Cabin | Private kitchen | Fridge, microwave, coffee/tea maker, electric kettle
Maple Leaf Motel
Maple Leaf Motel
Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (551 reviews)
The price is CNY747
CNY845 total
includes taxes & fees
Jan 11 - Jan 12
Maple Leaf Motel
Front of property
Silver Bay YMCA Inn and Conference Center
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, (137 reviews)
The price is CNY754
CNY837 total
includes taxes & fees
Jan 11 - Jan 12
Silver Bay YMCA Inn and Conference Center
Terrace/patio
Lodges At Cresthaven
Lodges At Cresthaven
Lodges At Cresthaven
4.0 star property
Lake George
9.4 out of 10, Exceptional, (549 reviews)
Lodges At Cresthaven
Flat-screen TV, DVD player
Sun Castle Resort
Sun Castle Resort
Sun Castle Resort
3.5 star property
Lake George
9.0 out of 10, Wonderful, (62 reviews)
The price is CNY1,666
CNY2,746 total
includes taxes & fees
Jan 11 - Jan 12
Sun Castle Resort
Garden
Pinebrook Motel
Pinebrook Motel
Pinebrook Motel
2.0 star property
Lake George
7.4 out of 10, Good, (187 reviews)
The price is CNY470
CNY521 total
includes taxes & fees
Jan 11 - Jan 12
Pinebrook Motel
Private beach, kayaking, rowing
Sundowner on Lake George
Sundowner on Lake George
Sundowner on Lake George
2.5 star property
Lake George
7.6 out of 10, Good, (245 reviews)
The price is CNY488
CNY1,123 total
includes taxes & fees
Jan 12 - Jan 13
Sundowner on Lake George
Premium bedding, desk, laptop workspace, blackout drapes
Courtyard by Marriott Lake George
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)
The price is CNY761
CNY844 total
includes taxes & fees
Feb 2 - Feb 3
Courtyard by Marriott Lake George
Property entrance
Lake Haven Motel
Lake Haven Motel
Lake Haven Motel
2.5 star property
Lake George
7.4 out of 10, Good, (110 reviews)
The price is CNY1,323
CNY2,049 total
includes taxes & fees
Jan 12 - Jan 13
Lake Haven Motel
Private beach, sun loungers, kayaking
Surfside On The Lake
Surfside On The Lake
Surfside On The Lake
2.5 star property
Lake George
8.0 out of 10, Very Good, (738 reviews)
Surfside On The Lake
Bar (on property)
The Inn of Lake George
The Inn of Lake George
The Inn of Lake George
2.5 star property
Lake George
9.6 out of 10, Exceptional, (106 reviews)
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
Howard Johnson by Wyndham Lake George
2.0 star property
Lake George
8.0 out of 10, Very Good, (1,000 reviews)
The price is CNY691
CNY767 total
includes taxes & fees
Jan 31 - Feb 1
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

Budget hotels in Chestertown and vicinity

Garden
Pinebrook Motel

Pinebrook Motel

Pinebrook Motel
2.0 star property
Lake George
7.4 out of 10, Good, (187)
The price is CNY470
CNY521 total
includes taxes & fees
Jan 11 - Jan 12
Pinebrook Motel
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 budget hotels

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 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
"The room was clean, beautiful and full of old school charm. We loved the holiday decorations in the lobby. "
Jennifer 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 CNY521 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.

Keep exploring