Photo by Julie Miller

Find Beach Hotels in Chestertown, NY

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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
8.8 out of 10, Excellent, (84)
"Great room, very nice staff. Nice weekend getaway."
The price is AED 862
AED 957 total
includes taxes & fees
24 Dec - 25 Dec
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 2,156
AED 2,393 total
includes taxes & fees
23 Dec - 24 Dec
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
Living area

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

10.0 out of 10, Exceptional, (24)
"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
Cozy retreat with fireplace, kayaks, and shared beach/pond access

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

9.0 out of 10, Wonderful, (16)
"Beautiful place wood location"
Cozy retreat with fireplace, kayaks, and shared beach/pond access
Peaceful Lakeside Retreat with Private Beach
Lake

Peaceful Lakeside Retreat with Private Beach

9.2 out of 10, Wonderful, (17)
"It was clean, nicely decorated, everything was new and in working order. Would suggest adding some face/wash cloths and top sheet for bed. Also, bed was comfortable but squeaked every time you made a move. All in all nice property and enjoyed our time :)"
Peaceful Lakeside Retreat with Private Beach
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, (54)
"It’s a wonderful place beautiful fireplace cozy cabin. Bed is so comfy. Just know there is only one bathroom but it’s big and nice. Worth the stay. "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Secluded gem with forest view, beach access & W/D

Secluded gem with forest view, beach access & W/D

7.8 out of 10, Good, (15)
"Overall the online listing is a very accurate representation of the property. It has a very rustic cabin feel. The pond that you can visit is wonderful and well staffed and taken care of. My only complaint is there was no air conditioning in the apartment and it got very hot."
The price is AED 213
AED 684 total
includes taxes & fees
23 Dec - 24 Dec
Secluded gem with forest view, beach access & W/D
Lakefront cabin with beautiful loft, game room, views, private dock

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

9.0 out of 10, Wonderful, (34)
"House was fine. Could be deep cleaned fan blades Cobb wed ect."
Lakefront cabin with beautiful loft, game room, views, private dock
Serene getaway with fireplace, grill, kayaks & washer/dryer

Serene getaway with fireplace, grill, kayaks & washer/dryer

9.6 out of 10, Exceptional, (8)
"A lovely get away"
Serene getaway with fireplace, grill, kayaks & washer/dryer
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 spa 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.