Chestertown Holidays
Book a Hotel + Flight or Car together to unlock savings
Photo by Julie Miller
- Plan, book, travel with confidence
- Better togetherSave up to Rp173.195 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
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
9.2/10 Wonderful! (145 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 Rp4.000.044 per night from 7 Nov to 8 Nov
Rp4.000.044
Rp4.440.062 total
7 Nov - 8 Nov
includes taxes & fees
8.6/10 Excellent! (102 reviews)
Staff was great. The inn is unique. Perfect!
Reviewed on 7 Sept 2025
The Queensbury Hotel
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,395 reviews)
Beautiful, clean, comfortable stay. The pub had great service, food and waitstaff. Breakfast was delicious and great service. Wonderful location and easy to walk to other places downtown. We will be back!❤️
Reviewed on 26 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.
More trip options
Expedia's Latest Trends
Hotels
- Hotels with smoking rooms in Carlsbad
- Hotels with smoking rooms in Jamestown
- Hotels with smoking rooms in Sanford
- Hotels with smoking rooms in Mountain Home
- Hotels with smoking rooms in Danville
- Hotels with smoking rooms in Cookeville
- Gay-Friendly Hotels in Hot Springs
- Hotels with smoking rooms in Collinsville
- Hotels in Ithaca
- Hotels with smoking rooms in Poughkeepsie
- Hotels with smoking rooms in Kingsland
- Hotels with smoking rooms in Rolla
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
