Photo by Julie Miller

Hotels in Chestertown

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Tonight
Apr 22 - Apr 23
Tomorrow
Apr 23 - Apr 24
This weekend
Apr 24 - Apr 26
Next weekend
May 1 - May 3

Where to stay in Chestertown?

Exterior
Pine Tree Motel & Cabins
Pine Tree Motel & Cabins
2.0 star property
Chestertown
9.2 out of 10, Wonderful, (146 reviews)
This motel offers complimentary WiFi and parking in Chestertown. Enjoy the outdoor terrace or play volleyball on site, with bike repair services available. Loon Lake Beach and Loon Lake attractions are located nearby for day trips.
The price is $175
$194 total
includes taxes & fees
May 16 - May 17
Pine Tree Motel & Cabins
Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn
Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (103 reviews)
The price is $241
$267 total
includes taxes & fees
Apr 27 - Apr 28
Friends Lake Inn
Lake view
The Fern Lodge
The Fern Lodge
3.5 star property
Chestertown
10.0 out of 10, Exceptional, (53 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 price is $446
$495 total
includes taxes & fees
Apr 23 - Apr 24
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 $145
$161 total
includes taxes & fees
Apr 23 - Apr 24
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 $1,074
$1,420 total
includes taxes & fees
Apr 23 - Apr 24
HIGHLANDS CASTLE overlooking Lake George.. plus 2 other Castles!
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, (217 reviews)
The price is $149
$165 total
includes taxes & fees
May 3 - May 4
Gore Mountain Lodge
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, (678 reviews)
The price is $123
$147 total
includes taxes & fees
Apr 23 - Apr 24
The Alpine 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, (446 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 $146
$162 total
includes taxes & fees
Apr 23 - Apr 24
North Creek Lodge at Gore Mountain
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
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 $254
$845 total
includes taxes & fees
Apr 26 - Apr 27
10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home
WiFi
Lake George Escape - Campground
Lake George Escape - Campground
2.0 star property
Diamond Point
8.4 out of 10, Very Good, (169 reviews)
The price is $122
$135 total
includes taxes & fees
May 10 - May 11
Lake George Escape - Campground
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, (1,003 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 $74
$82 total
includes taxes & fees
Apr 23 - Apr 24
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, (451 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.
The price is $115
$162 total
includes taxes & fees
Apr 23 - Apr 24
Lodge at Schroon Lake
Outdoor pool
The Villas on Lake George
The Villas on Lake George
2.5 star property
Diamond Point
7.6 out of 10, Good, (95 reviews)
The price is $165
$183 total
includes taxes & fees
May 18 - May 19
The Villas on Lake George
Exterior
The Juliana Resort
The Juliana Resort
2.5 star property
Diamond Point
8.8 out of 10, Excellent, (180 reviews)
Nestled in Diamond Point, this beach hotel offers a private shoreline for kayaking and canoeing. Just a 15-minute drive from Lake George and Six Flags, you'll appreciate the terrace, garden, free WiFi and parking while exploring nearby attractions.
The price is $92
$102 total
includes taxes & fees
May 17 - May 18
The Juliana Resort
Apartment (0 Bedroom) | Interior
< 1 Mi to Boat Launch! Schroon Lake Basecamp
< 1 Mi to Boat Launch! Schroon Lake Basecamp
3.0 star property
Schroon Lake
The price is $86
$163 total
includes taxes & fees
Apr 26 - Apr 27
< 1 Mi to Boat Launch! Schroon Lake Basecamp
Property grounds
Amber Lantern Lake George Motel and Cottage Rentals
Amber Lantern Lake George Motel and Cottage Rentals
2.0 star property
Lake George
8.4 out of 10, Very Good, (312 reviews)
Wake up near pristine shores at this Lake George motel with an outdoor pool. Just a short drive from Six Flags Great Escape, this cozy retreat offers free WiFi and parking. Guests praise the helpful staff while enjoying nearby Hearthstone Point Campground.
The price is $125
$139 total
includes taxes & fees
May 15 - May 16
Amber Lantern Lake George Motel and Cottage Rentals
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, (576 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 $99
$112 total
includes taxes & fees
Apr 23 - Apr 24
Maple Leaf Motel
Exterior
Depe Dene Lakeside Resort
Depe Dene Lakeside Resort
2.0 star property
Lake George
8.8 out of 10, Excellent, (423 reviews)
Wake to spectacular sunrises at this quiet Lake George resort with a pristine private beach and crystal-clear waters. Kayak on the lake, cool off in the seasonal outdoor pool, and watch magnificent sunsets from your patio.
The price is $89
$99 total
includes taxes & fees
May 14 - May 15
Depe Dene Lakeside Resort
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, (142 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 $104
$115 total
includes taxes & fees
Apr 23 - Apr 24
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, (576 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.
The price is $220
$244 total
includes taxes & fees
Apr 23 - Apr 24
Lodges At Cresthaven
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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Showing deals for:May 1 - May 3
Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (103 reviews)
The price is $250
per night
$554 total
includes taxes & fees
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Friends Lake Inn

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 April
Currently viewing crowd sizes and weather for April.
Typical weather for Chestertown
April
High 11°C / low 1°C. Cloudy most days.
View properties in April
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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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19°
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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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23°
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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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27°
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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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26°
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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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14°
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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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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.
-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

4.4/5 (8 reviews)
Loon Lake is 3.2 mi (5.2 km) from central Chestertown, why not stop by during your stay.
See properties

Friends Lake

4.7/5 (14 reviews)
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
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 amenities and great location "
Luis 1-night trip
Posted 4 hours ago
The Queensbury Hotel

Frequently asked questions

What accommodations do travelers like in Chestertown?
Guests like North Creek Lodge at Gore Mountain.
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 20 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.