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Find Beach Hotels in Chestertown, NY

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Check availability on Chestertown Beach Hotels

Top Chestertown Beach Hotels

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"I would definitely stay here again."
The price is SARĀ 657
SARĀ 729 total
includes taxes & fees
22 Jun - 23 Jun
Pine Tree Motel & Cabins

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 Fern Lodge

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (89)
"Quiet lodging and friendly staff"
The price is SARĀ 793
SARĀ 880 total
includes taxes & fees
24 Jun - 25 Jun
Friends Lake Inn

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

10.0 out of 10, Exceptional, (32)
"What an adorably cute, warm, welcoming location so glad we picked this place. Everything was clean the beds were comfortable and the neighborhood completely safe. "
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"The area was quiet and house was nice. Perfect for our needs."
Peaceful Lakeside Retreat with Private Beach

Cozy retreat with fireplace, kayaks, and shared beach/pond access

9.0 out of 10, Wonderful, (17)
"We love the house super clean , the we love the area very peace and quiet , we love the private beach and the fresh air , definitely we be back again "
Cozy retreat with fireplace, kayaks, and shared beach/pond access

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (109)
"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

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

10.0 out of 10, Exceptional, (61)
"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

NEW for 2024, 6 person hot tub. Spacious country home with large back yard.

10.0 out of 10, Exceptional, (15)
"Very clean, working hot tub, great electric fireplace, effective communication w the owner, and easy check in! Would absolutely rent from them again! "
NEW for 2024, 6 person hot tub. Spacious country home with large back yard.

3 bedroom cabin in Chestertown with hot tub, fireplace, fire pit, wifi, and more

10.0 out of 10, Exceptional, (6)
"Everything was great and appreciate the good communication and cleanliness of our accomodations "
3 bedroom cabin in Chestertown with hot tub, fireplace, fire pit, wifi, and more
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.

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.