Chestertown Trips (flight + hotel)

Photo by Julie Miller

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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.

Top hotels in Chestertown

Pine Tree Motel & Cabins
Pine Tree Motel & Cabins
2 out of 5
5537 State Route 8, Chestertown, NY
The price is P10,005 per night from Jun 24 to Jun 25
P10,005
P11,105 total
Jun 24 - Jun 25
includes taxes & fees
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"

Reviewed on Oct 28, 2024

Pine Tree Motel & Cabins
The Fern Lodge
The Fern Lodge
3.5 out of 5
46 Fiddlehead Bay Rd., Chestertown, NY
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."

Reviewed on Aug 27, 2024

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The Fern Lodge
The Queensbury Hotel
The Queensbury Hotel
3 out of 5
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,251 reviews)
"Good locations, quiet, big room (considering just coming from a trip in Japan 😀), clean, nice staff!"

Reviewed on Jun 22, 2025

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The Queensbury Hotel
See all 1,539 properties in Chestertown
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.

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?
To score cheap Chestertown vacation packages, organize 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-organized 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 vacation for longer.
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 traveling with the family or getting away 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.
How to plan a trip to Chestertown?

  1. Pick your dates: What you'd like to do in Chestertown and your favorite season can help you decide when to travel.
  2. 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.
  3. 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.
  4. Bundle your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the ideal Chestertown vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.