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Find hotels in Chestertown, NY from ฿2,063

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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

Loon Lake

Loon Lake's crystal-clear waters provide a peaceful Adirondack Mountain retreat for outdoor enthusiasts. Rent a kayak to glide across the serene surface or cast a line for native fish from the sandy public beach.
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Friends Lake

This private Adirondack gem offers pristine waters and tranquil surroundings away from tourist crowds. Stay at Friends Lake Inn to access swimming, fishing, and kayaking in this exclusive 450-acre natural retreat.
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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.

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A winter scene
Photo by Julie Miller
Open Photo by Julie Miller

Top Chestertown Hotel Reviews

More cheap stays in Chestertown

Best Western of Lake George

Best Western of Lake George

2452 State Route 9N Lake George NY
The price is ฿1,859 per night from 25 Dec to 26 Dec
฿1,859
฿2,063 total
25 Dec - 26 Dec
includes taxes & fees
7.6/10 Good! (1,002 reviews)

Frequently asked questions

Where is the best place to stay in Chestertown?
Based on our traveller data, Friends Lake Inn is one of the top choices for your stay. This hotel offers a restaurant and free parking. Other good options for your stay include Pine Tree Motel & Cabins and The Fern Lodge. See all available top hotels, or 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. 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 Queensbury Hotel: Offers 2 restaurants, an indoor pool and 2 bars. The Georgian Lakeside Resort and Holiday Inn Resort Lake George - Adirondack Area by IHG are two additional hotels that offer an on-site pool. View all hotels with pools 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 111 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.