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Search Beach Resorts & Hotels in Chestertown

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Check availability on Chestertown Beach Resorts & Hotels

Our top choices for Chestertown beach hotels

Exterior
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins
2.0 star property
Chestertown
9.2 out of 10, Wonderful, (146)
"Excellent location and staff was very friendly."
United States
Logan
Pine Tree Motel & Cabins
Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn

Friends Lake Inn

Friends Lake Inn
4.0 star property
Chestertown
8.6 out of 10, Excellent, (102)
"Friendly staff, room was clean, well maintained. Ate at the restaurant, food was great. "
United States
Erin
Friends Lake Inn
Lake view
The Fern Lodge

The Fern Lodge

The Fern Lodge
3.5 star property
Chestertown
9.8 out of 10, Exceptional, (50)
"Absolutely beautiful "
United States
Dana
The Fern Lodge
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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Frequently asked questions

What is Chestertown like for travellers who love the beach?
Known for its lakeside setting, Chestertown offers a lot for the traveller planning a getaway.
When's the best time for a beach holiday in Chestertown?
Plan your trip to the beach with a look at the seasons 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.
What is there to see and do around Chestertown?
After arriving and checking into your hotel, you'll probably want to explore your surroundings. If you're eager to check out the beaches, head to Veterans Memorial Park Beach or Rogers Memorial Park Beach for some relaxation by the water. Discover the area's lakeside setting, and make time for local attractions such as Loon Lake Beach and Friends Lake. Other things to see and do in the area are Loon Lake and Hudson River.
What's the best way to get to my beach hotel in Chestertown?
Here's some information to help you get to and around your beach accommodation in Chestertown more easily: Make your way to Chestertown with a flight to Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest major airport which is located 23.6 mi (38 km) from the city centre. If you'd like to venture out around the area, you may want a rental car for your journey.