
Chestertown Holidays
Photo by Julie Miller
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Chestertown Beach Holiday
Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown holiday. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organise your trip to Chestertown the quick and easy way by locking in one of our Chestertown holiday deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 3 kilometres from the downtown area.
Top hotels in Chestertown

Pine Tree Motel & Cabins
5537 State Route 8, Chestertown, NY
The price is €167 per night from 13 Aug to 14 Aug
€167
13 Aug - 14 Aug
includes taxes & fees
9.2/10 Wonderful! (133 reviews)
"Off the beaten path. Definitely not top notch but acceptable for a camping type atmosphere."
Reviewed on 1 Aug 2025

Friends Lake Inn
963 Friends Lake Rd, Chestertown, NY
The price is €213 per night from 13 Aug to 14 Aug
€213
13 Aug - 14 Aug
includes taxes & fees
8.6/10 Excellent! (96 reviews)
"Very nice location. Would have enjoyed more activity like hiking or a pool or something on site. But it met our requirements for a beautiful place to stay with good food"
Reviewed on 3 Aug 2025

The Queensbury Hotel
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,314 reviews)
"The bed was very comfortable, great night’s rest. We had an amazing breakfast, great service."
Reviewed on 10 Aug 2025
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.
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.