Photo by Julie Miller

Find beach hotels in Chestertown, NY from CA $112

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Top Chestertown Beach Hotel

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
10.0 out of 10, Exceptional, 20 reviews
"A wonderful home base for a week of skiing at Gore"
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
10.0 out of 10, Exceptional, 38 reviews
"The place was amazing!!! So clean and had everything you need to stay away from home!!! Our do Oliver especially loved playing with Ruby and Pearl!!!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Eagles Nest @ Loon Lake near Gore Mountain
10.0 out of 10, Exceptional, 102 reviews
"Great place to stay for gore mountain, will come again"
The price is CA $429
CA $992 total
includes taxes & fees
Jun 13 - Jun 14
Eagles Nest @ Loon Lake near Gore Mountain
Serene getaway with fireplace, grill, kayaks & washer/dryer
10.0 out of 10, Exceptional, 5 reviews
"A lovely get away"
Serene getaway with fireplace, grill, kayaks & washer/dryer
Chestertown Hideaway w/ Lake & Beach Access!
10.0 out of 10, Exceptional, 6 reviews
"This was a wonderful stay in a great location. We came to ski at Gore and this house was a perfect location. Lovely newer house with plenty of room for our family of four. Loved OP Fredericks restaurant which me could see from the house!!"
Chestertown Hideaway w/ Lake & Beach Access!
TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
10.0 out of 10, Exceptional, 87 reviews
"The host made us feel welcome. We enjoyed the privacy and the private pond access where canoes & gear were available! Highly recommended!"
TRIPP LAKE RETREAT sleeps 7 and is a great place to make Adirondack memories!
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, 42 reviews
"Paradise just simply heavenly. And so well appointed. Feel so at home"
The price is CA $816
CA $906 total
includes taxes & fees
Jun 5 - Jun 6
The Fern Lodge
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
9.8 out of 10, Exceptional, 46 reviews
"We recently stayed at the cottage and had a wonderful time. It has a very spacious kitchen and living room area for all to enjoy. There are so many DVDs and games to keep us entertained throughout the week. Patrick was an excellent host and very responsive."
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore
9.8 out of 10, Exceptional, 73 reviews
"We had a great stay. Very nice cabin. Only took off a star because there weren’t any towels and the dryer didn’t work. Otherwise, highly recommend."
Year round Log Cabin on 2 acres on Loon Lake. Minutes from Gore
Lily Pad South at Loon Lake near Gore Mountain
9.8 out of 10, Exceptional, 39 reviews
"What I loved most was it was like staying in your own home, quiet, clean, and private. The only drawback was no coffee in the kitchen. Otherwise absolutely give stars. I want to stay in this exact house again if welcome. They were very nice, too, and accommodating. "
Lily Pad South at Loon Lake near Gore Mountain
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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.

Popular beach getaways

Most booked beach stays in Chestertown in 2024

Chestertown Beach Hotel information

 

Beach Hotel in Chestertown

66

Highest price
CA $816
Cheapest price
CA $112
Number of guest reviews
409
Total number of hotels in Chestertown
1,517

 

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 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.

Recent Reviews in Chestertown
Expedia verified reviews