Chestertown Vacations
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Find the Best Chestertown Vacation Packages
Chestertown Beach Vacation
Escape the stresses of daily life and let your body, mind and soul completely relax during your Chestertown vacation. Few things are more invigorating than the cool sea breeze and the soothing sound of waves lapping at the shore. Organize your trip to Chestertown the quick and easy way by locking in one of our Chestertown vacation deals. Many visitors opt to base themselves near Loon Lake Beach, a must-see only 3 kilometers from the downtown area.
Chestertown Hotel Deals
Pine Tree Motel & Cabins
5537 State Route 8 Chestertown NY
9.2/10 Wonderful! (146 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 2025/10/5
Friends Lake Inn
963 Friends Lake Rd Chestertown NY
8.6/10 Excellent! (102 reviews)
Staff was great. The inn is unique. Perfect!
Reviewed on 2025/9/7
The Queensbury Hotel
88 Ridge St Glens Falls NY
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,423 reviews)
Clean room & friendly staff.
Reviewed on 2025/11/13
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.
Discover the most popular places to visit in Chestertown
Loon Lake Beach
If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.
Other vacations you might like
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
