The Best Beach Hotels in Chestertown, NY from ￥27,440 in 2024

Check availability on Chestertown Beach Hotels

Pick from 4 Chestertown Beach Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

"Paradise just simply heavenly. And so well appointed. Feel so at home"

￥104,244 total

includes taxes & fees

Jun 4 - Jun 5

Premier Room | 1 bedroom, premium bedding, individually decorated

"The food was made to order and very good prices were fair. The cost to stay there is overpriced."

￥49,085 total

includes taxes & fees

Jun 2 - Jun 3

"Cutest cabins, friendly owners, dog friendly ❤️ supporting small businesses definitely going back next year. "

￥30,458 total

includes taxes & fees

Jun 2 - Jun 3

Chestertown Beach Hotels information

Beach Hotels in Chestertown	4
Highest price	￥93,915
Cheapest price	￥27,440
Number of guest reviews	227
Total number of hotels in Chestertown	1,502

Frequently asked questions

What is Chestertown like for travelers who love the beach?

Known for its lakeside setting, Chestertown offers a lot for the traveler planning a getaway.

What's the best accommodation to stay near the beach in Chestertown?

The Fern Lodge is a top beach B&B with free breakfast and 8 spa tubs, and it’s located close to Loon Lake Beach.

How many beach hotels can I expect to find in Chestertown?

Choose from one of Expedia’s 25 hotels in Chestertown for your beachside break.

When's the best time for a beach vacation 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 temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches 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 Rogers Memorial Park Beach or Veterans Memorial Park Beach for some relaxation by the water. Discover the area’s lakeside setting, and make time for local attractions like 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 center. If you’d like to venture out around the area, you may want to rent a car for your trip.