Photo by Julie Miller

Find Beach Hotels in Chestertown, NY

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Check availability on Chestertown Beach Hotels

Compare Chestertown Beach Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
9.0 out of 10, Wonderful, (87)
"Location "
The price is AED 819
AED 909 total
includes taxes & fees
10 Apr - 11 Apr
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The price is AED 2,134
AED 2,369 total
includes taxes & fees
11 Apr - 12 Apr
The Fern Lodge
Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"
Pine Tree Motel & Cabins
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Smart TV, fireplace, foosball, books

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

10.0 out of 10, Exceptional, (30)
"My wife and I absolutely loved our stay at Jackson's Lodge! The cabin is very spacious and contains all the amenities you need. The hot tub was an amazing experience at the end of a long day. The Simpsons arcade machine was a personal favorite! Would definitely stay here again."
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Fridge, microwave, oven, stovetop

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (60)
"My family and i had a great time here! The place is Amazing and we would definitely stay again! "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Eagles Nest at Loon Lake near Gore Mountain
Exterior

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (107)
"Well-appointed house, very clean, well-equipped kitchen, host was easy to contact and attentive, steep driveway but was cleared very well, enough parking, game room was nice surprise, downstairs beds were on the small size, grounds were snow covered but appeared to be nicely landscaped and cared for, overall excellent stay."
Eagles Nest at Loon Lake near Gore Mountain
Chestertown Hideaway w/ Lake & Beach Access!
Property grounds

Chestertown Hideaway w/ Lake & Beach Access!

9.8 out of 10, Exceptional, (14)
"Great sized house for a family of 5. Beautiful, new and well decorated, it was just the right size for a family weekend away to ski. Fireplace was a great touch. Owner was extremely nice and responsive. Overall we had a great stay and would go back! "
Chestertown Hideaway w/ Lake & Beach Access!
Lakefront cabin with beautiful loft, game room, views, private dock
Exterior

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (36)
"Plenty of room for everyone, warm and relaxing."
Lakefront cabin with beautiful loft, game room, views, private dock
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Interior

Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain

9.8 out of 10, Exceptional, (87)
"Great location and easy to find. Responsive host. Nicely stocked kitchen. Only issue we ran into were not enough towels for 10 people. Otherwise loved the stay and felt like it was great value!"
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Luxury Adirondack getaway with 4 private ensuites
Property grounds

Luxury Adirondack getaway with 4 private ensuites

Luxury Adirondack getaway with 4 private ensuites
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 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 hot 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 Loon Lake Beach or Rogers Memorial Park Beach for some relaxation by the water. Discover the area’s lakeside setting, and make time for local attractions like Friends Lake and Loon Lake. Other things to see and do in the area are Hudson River and Tripp Pond.
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.