Chestertown Vacations
Book a Hotel + Flight or Car together to unlock savings
Your Chestertown Vacation
There's plenty to like about Chestertown, from its rich history to its spectacular views. When you're ready to spend a bit of time in this interesting city, our Chestertown vacation packages will be ideal for you. Friends Lake, Loon Lake and Loon Lake Beach are just a few of the sights you'll want to see during your trip to Chestertown. Don't put off your visit to this destination any longer. Your dream Chestertown vacation is only a few clicks away with Expedia.
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.
Chestertown Hotel Deals
Pine Tree Motel & Cabins
5537 State Route 8 Chestertown NY
Fully refundableReserve now, pay when you stay
$175 nightly
$194 total
Aug 31 - Sep 1
Total with taxes and fees
9.2/10 Wonderful! (160 reviews)
"Really clean. Very quaint. Lovely owners. Close to “town” and close to lake. Perfect for our purposes."
Reviewed on Aug 23, 2026
Peaceful Lakeside Retreat with Private Beach
Chestertown NY
9.4/10 Exceptional! (28 reviews)
"A beautiful condo close to Lake George."
Reviewed on Aug 22, 2026
La Quinta Inn & Suites by Wyndham Lake George
1533 US-9 Lake George NY
Fully refundableReserve now, pay when you stay
$91 nightly
$101 total
Sep 14 - Sep 15
Total with taxes and fees
8.6/10 Excellent! (1,661 reviews)
"Staff were kind and helpful Hot tub was closed ; Pool was huge but slide was dirty ; I think the hotel needs more cleaning . We had no hot water only warm but overall it was easy check in and out and great location."
Reviewed on Aug 29, 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.
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 2 miles (3 km) from the downtown area.
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 680 |
Max Temp Winter | 30ºF |
Max Temp Summer | 75ºF |
Top Sights | Gore Mountain Ski Resort, Loon Lake Beach and Natural Stone Bridge and Caves |
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Frequently asked questions
How much does a Chestertown vacation package cost?
You can snap up a vacation package to this destination on Expedia. But how much your vacation 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?
If you're looking to book a cheap Chestertown vacation package, consider visiting in February, November and December. You're likely to find lower rates on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Chestertown?
The ideal duration of your Chestertown vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to hit all the top sights and explore some hidden gems along the way.
Is it worth booking a vacation package to Chestertown?
Chestertown is a good vacation destination with attractions like Loon Lake Beach among the many things to keep you entertained. Whether you're heading away with the family or planning a trip with friends, a Chestertown vacation 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 vacation package as early as possible.
Is it cheaper to book a Chestertown vacation as a package?
Expedia vacation 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 personalized Chestertown vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation 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 vacation.
Does Expedia offer Book Now, Pay Later Chestertown vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Chestertown trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.