Top hotels in Chestertown
The Queensbury Hotel
88 Ridge St Glens Falls NY
Fully refundableReserve now, pay when you stay
3.155.017 ₫
3.501.912 ₫ total
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,651 reviews)
"It was good"
Reviewed on 10 Aug 2026
La Quinta Inn & Suites by Wyndham Lake George
1533 US-9 Lake George NY
Fully refundableReserve now, pay when you stay
2.650.636 ₫
2.942.207 ₫ total
31 Aug - 1 Sept
includes taxes & fees
Great Escape Lodge & Indoor Waterpark
89 Six Flags Dr Queensbury NY
5.321.147 ₫
5.906.472 ₫ total
7 Sept - 8 Sept
includes taxes & fees
8/10 Very good! (1,797 reviews)
"Good - water park included - free parking To be improved - having a continental breakfast for that kind of lodging would be logical.. - room insulation, having someone above that seem to weight 100 tons"
Reviewed on 10 Aug 2026
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.
Stay near popular Chestertown attractions
Loon Lake
8.8/10 (8 reviews)
Loon Lake's crystal-clear waters provide a peaceful Adirondack Mountain retreat for outdoor enthusiasts. Rent a kayak to glide across the serene surface or cast a line for native fish from the sandy public beach.
Friends Lake
9.4/10 (14 reviews)
This private Adirondack gem offers pristine waters and tranquil surroundings away from tourist crowds. Stay at Friends Lake Inn to access swimming, fishing, and kayaking in this exclusive 450-acre natural retreat.
Loon Lake Beach
8.4/10 (7 reviews)
Loon Lake Beach offers crystal-clear waters against the backdrop of the Adirondack Mountains. Enjoy a day of swimming and picnicking in this serene natural setting, where sandy shores meet lush greenery.
Tripp Pond
8.6/10 (4 reviews)
Tripp Pond offers a tranquil escape with calm waters surrounded by lush forests in Chestertown, New York. Enjoy peaceful fishing or kayaking while taking in the natural beauty of the Adirondack landscape.
Frequently asked questions
How much does a Chestertown holiday package cost?
You can snap up a holiday package to this destination on Expedia. But how much your holiday to Chestertown costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Chestertown?
To score cheap Chestertown holiday packages, organise your trip outside of peak times such as school holidays. You'll typically find better availability and lower prices in the off-season or when it's less busy.
How many days is enough for Chestertown?
With a well-organised itinerary, you can easily hit the main Chestertown attractions in a few days. But if you'd like to explore off the beaten track or take day trips, consider booking your Chestertown holiday for longer.
Is it worth booking a holiday package to Chestertown?
Chestertown is a good holiday destination with attractions like Loon Lake Beach among the many things to keep you entertained. Whether you're travelling with the family or getting away with friends, a Chestertown holiday promises a good time for everyone.
How to find the best Chestertown package deals?
Use Expedia's filter tool to find some tempting Chestertown package deals. When you start your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or search for Chestertown package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your holiday package as early as possible.
Is it cheaper to book a Chestertown holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalised Chestertown holiday by choosing your preferred accommodation type, airline and car class.
When to book a holiday package to Chestertown?
Enjoy incredible discounts by reserving your flights ahead of time with Expedia. If spontaneity is more your style, take advantage of our last-minute deals for an impromptu Chestertown holiday.
How to plan a trip to Chestertown?
- Pick your dates: What you'd like to do in Chestertown and your favourite season can help you decide when to travel.
- Set a budget: Consider expenses like flights, meals and transportation when calculating how much to set aside for your trip to Chestertown. Then, pick a hotel that works with your budget, whether that's a low-cost stay or a more luxurious retreat.
- Decide how long to go for: Now that you know more about Chestertown, you can figure out the ideal length of your break. Put together a rough itinerary and give yourself enough time to cover everything you want to do.
- Bundle your accommodation and airfare: After you've nailed down your trip dates and duration, lock in the ideal Chestertown holiday package for you.
