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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
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (129)
"Excellent location and staff was very friendly."
The price is AED 643
AED 713 total
includes taxes & fees
20 Jul - 21 Jul
Pine Tree Motel & Cabins
Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
The price is AED 862
AED 957 total
includes taxes & fees
21 Jul - 22 Jul
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"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
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Sun loungers

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

10.0 out of 10, Exceptional, (34)
"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, (62)
"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
Peaceful Lakeside Retreat with Private Beach
Beach nearby, sun loungers, beach towels

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
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
On the beach

#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!

9.6 out of 10, Exceptional, (16)
"The views were absolutely amazing! We will definitely be back."
#4 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Elizabeth. A Guest House Near Lake George.
Lake

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (42)
"It is an older house with a lot of character. For our very large family. The pool was super clean and a hit with everyone. Very convenient to lake George, and having a grocery store a very short walk away was a huge bonus!"
Elizabeth. A Guest House Near 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, (110)
"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
NEW for 2024, 6 person hot tub. Spacious country home with large back yard.
Terrace/patio

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

9.8 out of 10, Exceptional, (17)
"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.
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 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.