Photo by Julie Miller

Find Hotels on the Lake in Chestertown, NY from $175

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Pick from 5 Chestertown Hotels on the Lake and compare room rates, reviews, and availability. Most hotels are fully refundable.

Restaurant
The Fern Lodge
3.5 star property
9.8 out of 10, Exceptional, (42)
"Paradise just simply heavenly. And so well appointed. Feel so at home"
The price is $599
$665 total
includes taxes & fees
May 23 - May 24
The Fern Lodge
Premier Room | 1 bedroom, premium bedding, individually decorated
Friends Lake Inn
4.0 star property
9.0 out of 10, Wonderful, (77)
"The food was made to order and very good prices were fair. The cost to stay there is overpriced."
The price is $282
$313 total
includes taxes & fees
May 23 - May 24
Friends Lake Inn
Exterior
Pine Tree Motel & Cabins
2.0 star property
9.0 out of 10, Wonderful, (113)
"Cutest cabins, friendly owners, dog friendly ❤️ supporting small businesses definitely going back next year. "
The price is $175
$194 total
includes taxes & fees
May 23 - May 24
Pine Tree Motel & Cabins
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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.

Chestertown Hotels on the Lake information

 

Hotels on the Lake in Chestertown

5

Highest price
$599
Cheapest price
$175
Number of guest reviews
227
Total number of hotels in Chestertown
1,495

 

Frequently asked questions

Why book your lakeside hotel in Chestertown with Expedia?
Expedia has unbeatable deals on lakeside hotels in Chestertown. But our incredible prices are just the start. You’ll discover a wide variety of hotels to select from and clever search filters that make it a breeze to find your dream stay.
How can I find cheap lakeside hotels in Chestertown?
Use Expedia’s filters to set your price per night budget. Then, select your preferred hotel star rating — they start from basic (1 star) to luxury (5 star). You can also search based on an area you want to stay in. Finding your dream lakeside hotel in Chestertown at the right price couldn’t be easier!
What is there to do in Chestertown near my lakeside hotel?
Whatever you love doing, Chestertown has tons of things to keep you occupied. Loon Lake Beach, Natural Stone Bridge and Caves and Friends Lake are on many visitors’ agendas. Don’t forget to explore Avalanche Lake, Loon Lake and Tripp Pond either. With Expedia’s Chestertown hotel deals, you can see more terrific attractions like these with the money you save.

Recent reviews of Chestertown hotels
Expedia verified reviews

The Georgian Lakeside Resort

The Georgian Lakeside Resort

5/5 Excellent
"This was my first visit to lake george and I choose this property because of the view. The staff was wonderful answering all questions myself and my spouse had giving great suggestions about places for us to see. They were remodeling and their restaurant wasn't finished yet but their selecting for breakfast was wonderful. I will definitely be visiting again as they made my birthday wonderful. "
A verified traveler stayed at The Georgian Lakeside Resort
Posted 1 day ago
The Georgian Lakeside Resort