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

This weekend
Jul 31 - Aug 2
Next weekend
Aug 7 - Aug 9

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, (154 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
Jul 28 - Jul 29
Pine Tree Motel & Cabins
Premier Room | 1 bedroom, premium bedding, iron/ironing board, WiFi (free)

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.8 out of 10, Excellent, (112 reviews)
The price is $164
$182 total
includes taxes & fees
Jul 28 - Jul 29
Friends Lake Inn
Lake view

The Fern Lodge

The Fern Lodge
3.5 star property
Chestertown
9.8 out of 10, Exceptional, (57 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 $495
$549 total
includes taxes & fees
Aug 23 - Aug 24
The Fern Lodge
Exterior

Super 8 by Wyndham Lake George/Warrensburg Area

Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
Lake George
8.6 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 $93
$103 total
includes taxes & fees
Aug 9 - Aug 10
Super 8 by Wyndham Lake George/Warrensburg Area
Exterior

Llama House ADK

Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (36 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 $112
$124 total
includes taxes & fees
Jul 28 - Jul 29
Llama House ADK
Premium Room | Premium bedding, down comforters, iron/ironing board, WiFi (free)

The Alpine Lodge

The Alpine Lodge
3.0 star property
North Creek
9.0 out of 10, Wonderful, (687 reviews)
The price is $144
$171 total
includes taxes & fees
Aug 5 - Aug 6
The Alpine Lodge
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, (168 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 $150
$167 total
includes taxes & fees
Aug 16 - Aug 17
Silver Bay YMCA Inn and Conference Center
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, (324 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 $88
$97 total
includes taxes & fees
Jul 28 - Jul 29
Amber Lantern Lake George Motel and Cottage Rentals
Indoor pool, outdoor pool, open 9:00 AM to 10:00 PM, pool umbrellas

Adirondack Retreat Inn & Suites

Adirondack Retreat Inn & Suites
2.5 star property
Lake George
9.4 out of 10, Exceptional, (1,004 reviews)
This peaceful motel offers clean rooms and attentive staff just minutes from Six Flags Great Escape. Enjoy volleyball courts, rowing activities, and a garden setting. The convenient location puts Lakeside Trail and Lake George attractions within easy reach.
The price is $116
$134 total
includes taxes & fees
Jul 29 - Jul 30
Adirondack Retreat Inn & Suites
Balcony

Studio 6 Lake George, NY - Adirondacks

Studio 6 Lake George, NY - Adirondacks
2.0 star property
Lake George
9.4 out of 10, Exceptional, (6 reviews)
The price is $101
$112 total
includes taxes & fees
Jul 29 - Jul 30
Studio 6 Lake George, NY - Adirondacks
Free daily continental breakfast

Best Western of Lake George

Best Western of Lake George
2.5 star property
Lake George
7.6 out of 10, Good, (1,011 reviews)
Perfectly positioned for walkable adventures near shopping centers and restaurants, this hotel offers a refreshing outdoor pool and complimentary continental breakfast. Guests consistently praise the helpful staff while enjoying free WiFi and parking during their Lake George escape.
The price is $100
$111 total
includes taxes & fees
Aug 6 - Aug 7
Best Western of Lake George
Reception

Admiral Motel

Admiral Motel
2.5 star property
Lake George
9.4 out of 10, Exceptional, (760 reviews)
The price is $136
$151 total
includes taxes & fees
Jul 28 - Jul 29
Admiral Motel
Deluxe Room, 2 Queen Beds, Refrigerator & Microwave | Laptop workspace, iron/ironing board (on request), WiFi (free)

Motel 6 Lake George, NY – Adirondacks

Motel 6 Lake George, NY – Adirondacks
2.5 star property
Lake George
9.0 out of 10, Wonderful, (203 reviews)
Colonial-style motel with hot tub and fitness center, just minutes from Six Flags Great Escape. Rooms include microwaves and refrigerators for added convenience, while free WiFi and parking enhance your Adirondack adventure.
The price is $90
$100 total
includes taxes & fees
Aug 27 - Aug 28
Motel 6 Lake George, NY – Adirondacks
Superior Apartment, 2 Bedrooms, Kitchen, Mountain View | Living area | 43-inch Smart TV with digital channels

The Motel Montreal

The Motel Montreal
2.0 star property
Lake George
7.2 out of 10, Good, (508 reviews)
Dive into outdoor adventure at this motel with complimentary parking just a short drive from Lake George and Six Flags Great Escape. Cool off in the seasonal pool after exploring nearby Lakeside Trail. The 24-hour front desk staff earns consistent praise from travelers.
The price is $47
$135 total
includes taxes & fees
Jul 29 - Jul 30
The Motel Montreal
Room, 2 Queen Beds, Non Smoking | Desk, WiFi (free), bed sheets

Howard Johnson by Wyndham Lake George

Howard Johnson by Wyndham Lake George
2.0 star property
Lake George
8.2 out of 10, Very Good, (1,022 reviews)
Just 10 minutes from Lake George and Six Flags Great Escape, this motel offers free WiFi and parking for easy adventures. After exploring nearby attractions, cool off in the outdoor pool. Friendly staff and clean rooms make this a traveler-favorite base camp.
The price is $110
$122 total
includes taxes & fees
Aug 17 - Aug 18
Howard Johnson by Wyndham Lake George
Exterior

Brookside Motel

Brookside Motel
2.5 star property
Lake George
8.6 out of 10, Excellent, (695 reviews)
Just 10 minutes from Lake George and Six Flags Great Escape, this motel offers complimentary WiFi and parking alongside a refreshing outdoor pool. Lakeside Trail awaits nearby for nature enthusiasts, with Albany International Airport less than an hour away.
The price is $84
$93 total
includes taxes & fees
Jul 28 - Jul 29
Brookside Motel
Exterior

The Juliana Resort

The Juliana Resort
2.5 star property
Diamond Point
8.8 out of 10, Excellent, (200 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 $199
$221 total
includes taxes & fees
Aug 25 - Aug 26
The Juliana Resort
Indoor pool

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
3.0 star property
Lake George
8.8 out of 10, Excellent, (1,678 reviews)
Wake up to complimentary breakfast before exploring Lake George attractions. This family-friendly hotel offers an indoor pool and hot tub for year-round relaxation. Just 10 minutes from Six Flags Great Escape with convenient free WiFi and parking.
The price is $118
$131 total
includes taxes & fees
Aug 23 - Aug 24
La Quinta Inn & Suites by Wyndham Lake George
Lobby

Wingate by Wyndham Lake George

Wingate by Wyndham Lake George
3.0 star property
Lake George
6.2 out of 10, (1,008 reviews)
This quiet retreat offers free continental breakfast, WiFi, and parking, with easy access to Lake George's attractions. Enjoy snorkeling and water skiing nearby, or try the seasonal downhill skiing options just minutes away.
The price is $94
$105 total
includes taxes & fees
Jul 29 - Jul 30
Wingate 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 July
Currently viewing crowd sizes and weather for July.
Typical weather for Chestertown
July
High 27°C / low 15°C. Sunny most days.
View properties in July
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°
-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°
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

8.8/10 (8 reviews)
Loon Lake is 3.2 mi (5.2 km) from central Chestertown, why not stop by during your stay. Chestertown has other popular natural features you might want to visit such as Lake George.
See properties

Learn more about Chestertown

Chestertown is well-known for its attractions such as Friends Lake and Loon Lake. The city has something for everyone including sights like Hudson River and Loon Lake Beach within a secluded setting.

See all hotels in Chestertown
A snowy lodge with cabins and tall pine trees.
Photo by Julie Miller
Open Photo by Julie Miller

Check out reviews of Chestertown hotels guests love

Scotty's Lakeside Resort

Scotty's Lakeside Resort

10/10 Excellent
"Outdoor amenities were beautiful & well kept. Great view from front porch. Room floor was not level so it was a bit weird to walk around the room. Exceeded my expectations overall. Would stay again."
STEPHANIE 3-night trip
Posted 1 hour ago
Scotty's Lakeside Resort

Frequently asked questions

What accommodations do travelers like in Chestertown?
Guests like Friends Lake Inn.
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 60 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.