Photo by Julie Miller

Find Beach Hotels in Chestertown, NY

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on Chestertown Beach Hotels

Tonight
22 Feb - 23 Feb
Tomorrow
23 Feb - 24 Feb
Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar

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

Friends Lake Inn
Property entrance

Friends Lake Inn

4.0 star property
9.0 out of 10, Wonderful, (87)
"Quiet lodging and friendly staff"
The price is AED 862
AED 957 total
includes taxes & fees
24 Feb - 25 Feb
Friends Lake Inn
The Fern Lodge
Room

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
25 Feb - 26 Feb
The Fern Lodge
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Living area

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

10.0 out of 10, Exceptional, (27)
"My family and friends would like to thank Tony and Kristi (the owners) for such a great vacation at their home in Chestertown. Everything on the description of the house was accurate. The house was super cozy and comfortable. It was clean and ready for us when we arrived. The owners were helpful with a few questions we had early in our stay and quick to respond. We brought our furry buddy Willow with us, and we are pretty sure she did not want to leave. There was plenty of room for her to...
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
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
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Great Room

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

10.0 out of 10, Exceptional, (57)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain
Lakefront cabin with beautiful loft, game room, views, private dock

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

9.2 out of 10, Wonderful, (35)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
Elizabeth. A Guest House Near Lake George.
Exterior

Elizabeth. A Guest House Near Lake George.

8.2 out of 10, Very Good, (39)
"The house has a lot of character. Great quiet neighborhood. Gas station, grocery store, pharmacy, and ice cream shop within walking distance. Dog park near by. Heated swimming pool was very nice and relaxing. Property manager made sure we were happy with our stay."
Elizabeth. A Guest House Near Lake George.
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Property grounds

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

9.8 out of 10, Exceptional, (83)
"This cabin had a large floor plan with lots of space for our family to gather. Large dining table for meals and board games, lots of seating around the fireplace and tv area. The bedrooms were all good size and accommodated four adults and teens. The cabin had everything we needed to cook meals. The owner was very friendly, accommodating and responsive."
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Chestertown Hideaway w/ Lake & Beach Access!
Chestertown Vacation Rental | 3BR | 2BA | 3 Stairs Required to Enter

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!
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.
Don't see what you're looking for?
See all available properties in Chestertown

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.