Photo by Julie Miller

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Top hotels and accommodation in Chestertown

Pine Tree Motel & Cabins
2.0 star property
9.2 out of 10, Wonderful, (143)
"Quiet, comfy, quaint, petite and the most pleasant staff."
United States
Matthew
Pine Tree Motel & Cabins
Friends Lake Inn
4.0 star property
8.6 out of 10, Excellent, (102)
"Staff was great. The inn is unique. Perfect!"
United States
Linda
The price is AU$380
includes taxes & fees
23 Oct - 24 Oct
Friends Lake Inn
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (48)
"Comfortable, friendly, beautiful lodge, spacious facilities"
Canada
Frederick
The Fern Lodge
La Quinta Inn & Suites by Wyndham Lake George
3.0 star property
9.0 out of 10, Wonderful, (1691)
"friendly staff , very clean , grounds well maintained , good breakfast "
United States
Tom
The price is AU$172
includes taxes & fees
10 Nov - 11 Nov
La Quinta Inn & Suites by Wyndham Lake George
The Georgian Lakeside Resort
2.5 star property
8.6 out of 10, Excellent, (1001)
"Very spacious clean would absolutely stay there again "
United States
Steven
The price is AU$183
includes taxes & fees
25 Oct - 26 Oct
The Georgian Lakeside Resort
The Queensbury Hotel
3.0 star property
9.4 out of 10, Exceptional, (1401)
"Really enjoyed lite food in bar area"
United States
Jim
The Queensbury Hotel
Fort William Henry Hotel and Conference Center
3.0 star property
8.4 out of 10, Very good, (1002)
"Very good for family vacation, good view, clean room, definitely will be back next time."
United States
Johan Des
The price is AU$204
includes taxes & fees
6 Nov - 7 Nov
Fort William Henry Hotel and Conference Center
Clarion Inn & Suites at the Outlets of Lake George
2.5 star property
8.4 out of 10, Very good, (1000)
"Beautiful balcony room, breakfast was up kept well, and property was quiet."
United States
Jose
The price is AU$152
includes taxes & fees
2 Nov - 3 Nov
Clarion Inn & Suites at the Outlets of Lake George
Super 8 by Wyndham Lake George/Downtown
2.0 star property
8.0 out of 10, Very good, (960)
"Staff called to verify stay, were very courteous and helpful even though we arrived very late in the evening, beds were great and beautiful areas to sit outside!! "
United States
Tambra
The price is AU$103
includes taxes & fees
28 Oct - 29 Oct
Super 8 by Wyndham Lake George/Downtown
Six Flags Great Escape Lodge & Indoor Waterpark
3.5 star property
7.8 out of 10, Good, (1344)
"Beautiful family fun hotel"
United States
Carolyn
The price is AU$291
includes taxes & fees
26 Oct - 27 Oct
Six Flags Great Escape Lodge & Indoor Waterpark
Howard Johnson by Wyndham Lake George
2.0 star property
8.0 out of 10, Very good, (1033)
"Property had a great location next to town. The staff was incredibly nice. I would certainly stay again."
United States
Ashley
The price is AU$101
includes taxes & fees
27 Oct - 28 Oct
Howard Johnson by Wyndham Lake George
Mohican Resort Motel
2.5 star property
9.0 out of 10, Wonderful, (166)
"Indoor pool are was real nice as well as game and fitness room. Staff was very accomadating. Will definately stay again. "
United States
Lorraine
Mohican Resort Motel
Lodges At Cresthaven
4.0 star property
9.4 out of 10, Exceptional, (514)
"Great, peaceful, well managed place with awesome views"
United States
Christopher
The price is AU$278
includes taxes & fees
9 Nov - 10 Nov
Lodges At Cresthaven
Lodge at Schroon Lake
3.0 star property
9.0 out of 10, Wonderful, (395)
"Absolutely loved this property! Beautiful location on lake, live music, great food. Staff super friendly and helpful. Looking forward to a return visit❤️"
United States
Cheryl
Lodge at Schroon Lake
Holiday Inn Resort Lake George - Adirondack Area by IHG
3.0 star property
9.2 out of 10, Wonderful, (1001)
"Clean, great amenities, softttttt sheets!"
United States
Leah
The price is AU$165
includes taxes & fees
16 Nov - 17 Nov
Holiday Inn Resort Lake George - Adirondack Area by IHG
Super 8 by Wyndham Lake George/Warrensburg Area
2.5 star property
8.6 out of 10, Excellent, (1007)
"Was close to people we were visiting. "
Canada
Linda
The price is AU$115
includes taxes & fees
28 Oct - 29 Oct
Super 8 by Wyndham Lake George/Warrensburg Area
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
3.0 star property
9.0 out of 10, Wonderful, (1259)
"Clean room, comfy beds, quiet, friendly staff! "
United States
Diane
The price is AU$164
includes taxes & fees
26 Oct - 27 Oct
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Courtyard by Marriott Lake George
3.0 star property
9.2 out of 10, Wonderful, (1000)
"Great hotel and location! "
United States
Jihane
The price is AU$203
includes taxes & fees
2 Nov - 3 Nov
Courtyard by Marriott Lake George
Trout House Village Resort
3.0 star property
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
United States
John
The price is AU$239
includes taxes & fees
23 Oct - 24 Oct
Trout House Village Resort
Surfside On The Lake
2.5 star property
8.0 out of 10, Very good, (725)
"Very nice too , loved 3rd floor balcony "
United States
Debra
Surfside On The Lake
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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Our guide on where to stay in Chestertown

Find the best Chestertown areas for the activities you enjoy most.

Chester Shores

While Chester Shores isn't home to many top sights, Loon Lake Beach and Loon Lake are some notable places to visit nearby.

Stay near popular Chestertown attractions

Learn more about Chestertown

Nestled in the Adirondacks, this charming town offers hiking trails and kayaking on Friends Lake during summer months. Winter visitors can hit the slopes at nearby Gore Mountain in North Creek or explore the Natural Stone Bridge and Caves in Pottersville.

Photo by Julie Miller
Open Photo by Julie Miller

Top Chestertown Hotel Reviews

More cheap accommodation in Chestertown

Frequently asked questions

Where is the best place to stay in Chestertown?
The Fern Lodge is a favourite property for Expedia customers. This B&B offers free breakfast and free parking. Other top choices based on reviews include Pine Tree Motel & Cabins and Friends Lake Inn. See all available top hotels, or vacation rentals in Chestertown.
What are some of the best holiday rentals that Chestertown has to offer?
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail: This holiday home rental outside of Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games. See all vacation rentals in Chestertown.
If I need to cancel my hotel reservation in Chestertown, will I receive a refund?
Yes, you'll find most room reservations are fully refundable if you cancel before the hotel's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you booked a non-refundable reservation, it might still be possible to cancel it and receive a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Chestertown.
What's the best LGBTQ-friendly hotel in Chestertown?
Pine Tree Motel & Cabins is one of the top choices for those in the LGBT community. See all available hotels listed as LGBTQ-friendly in Chestertown.
What's the best dog-friendly place to stay in Chestertown?
Pine Tree Motel & Cabins is a top dog-friendly option for your stay. Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing is another option if you're bringing your pet along. See more pet-friendly hotel accommodations in Chestertown.
What's the best hotel for a beach holiday in Chestertown?
The Fern Lodge is a top beach B&B with free breakfast and 8 hot tubs, and it's located close to Loon Lake Beach . See more stays near the beach in Chestertown.
What are some accommodation options with pools in Chestertown?
The Georgian Lakeside Resort: Hotel, 1-minute walk from Lake George. Provides a private beach, a seasonal outdoor pool and free self parking. The Queensbury Hotel and La Quinta Inn & Suites by Wyndham Lake George are two additional hotels that offer an on-site pool. View all hotels with pools in Chestertown.
What's the top hotel in Chestertown with an on-site water park or a water park nearby?
1970s acreage surrounded by trees with deck, grill, & internet is a favourite water park hotel in Chestertown
What is staying in Chestertown like?
Visitors to Chestertown will definitely enjoy the lakeside setting. Tourists can also enjoy the city's coffee shops, forests and seafood restaurants. In Chestertown, there are 118 hotels and other accommodation options to choose from. Find out more about Chestertown.
What is there to see in Chestertown?
Natural beauty is on display at Loon Lake Beach, Friends Lake and Loon Lake. A couple of additional sights to add to your itinerary are Hudson River and Tripp Pond. Take a look at what more there is to see and do in Expedia's Chestertown guide.
What's the seasonal weather like in Chestertown?
The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are January, March, November and December, with each month seeing an average of 33 cm of snowfall.

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