Photo by Julie Miller

Find Beach Hotels in Chestertown, NY

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Check availability on Chestertown Beach Hotels

Tonight
6 May - 7 May
Tomorrow
7 May - 8 May
This weekend
9 May - 11 May
Next weekend
16 May - 18 May

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

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
7 May - 8 May
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 2,156
AED 2,393 total
includes taxes & fees
7 May - 8 May
The Fern Lodge
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 680
AED 754 total
includes taxes & fees
18 May - 19 May
Pine Tree Motel & Cabins
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, (30)
"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
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, (60)
"Incredible place and stay, highly recommended!"
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Interior

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

9.8 out of 10, Exceptional, (87)
"Great location, very easy check in, good views, close to other places, we will definitely come again"
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain
Chestertown Hideaway w/ Lake & Beach Access!
Property grounds

Chestertown Hideaway w/ Lake & Beach Access!

9.8 out of 10, Exceptional, (14)
"Beautiful home. Great location for a Gore ski trip."
Chestertown Hideaway w/ Lake & Beach Access!
Lakefront cabin with beautiful loft, game room, views, private dock
Exterior

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

9.2 out of 10, Wonderful, (38)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock
Luxury Adirondack getaway with 4 private ensuites
Property grounds

Luxury Adirondack getaway with 4 private ensuites

Luxury Adirondack getaway with 4 private ensuites
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, (16)
"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
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 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.