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 14 Oct to 15 Oct
€167
14 Oct - 15 Oct
includes taxes & fees
9.2/10 Wonderful! (142 reviews)
"We attended the Warrensburg Largest Garage Sale Weekend. The Motel is only 20 minutes away from the event. Located near Chestertown so you can go out to eat or grab groceries at the local Grocery Store. Motel is Dog Friendly and we did not have any issues with the Wi-Fi."
Reviewed on 5 Oct 2025
Friends Lake Inn
963 Friends Lake Rd, Chestertown, NY
The price is €213 per night from 14 Oct to 15 Oct
€213
14 Oct - 15 Oct
includes taxes & fees
8.6/10 Excellent! (102 reviews)
"Staff was great. The inn is unique. Perfect!"
Reviewed on 7 Sept 2025
The Georgian Lakeside Resort
384 Canada Street, Lake George, NY
The price is €104 per night from 24 Oct to 25 Oct
€104
24 Oct - 25 Oct
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Very nice here"
Reviewed on 9 Oct 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
