Photo by Julie Miller

Find Beach Hotels in Chestertown, NY

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Check availability on Chestertown Beach Hotels

Tonight
2 Jun - 3 Jun
Tomorrow
3 Jun - 4 Jun
This weekend
6 Jun - 8 Jun
Next weekend
13 Jun - 15 Jun

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

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"I would definitely stay here again."
The price is AED 643
AED 713 total
includes taxes & fees
3 Jun - 4 Jun
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, (89)
"Quiet lodging and friendly staff"
The price is AED 819
AED 909 total
includes taxes & fees
3 Jun - 4 Jun
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 2,200
AED 2,442 total
includes taxes & fees
8 Jun - 9 Jun
The Fern Lodge
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, (31)
"We thoroughly enjoyed our stay and had a relaxing week."
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Outdoor dining

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
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, (61)
"Second time staying here and continues to meet all expectations. Owner and on site managers all friendly and responsive. "
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
3 bedroom cabin in Chestertown with hot tub, fireplace, fire pit, wifi, and more
Exterior

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

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

9.6 out of 10, Exceptional, (11)
"Absolutely loved our stay at Birchwood and we’d love to come back for many years to come!"
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
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.

10.0 out of 10, Exceptional, (14)
"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 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 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.