Chestertown Trips (flight + hotel)

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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

Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel
Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel
3 out of 5
2223 Canada St, Lake George, NY
Fully refundable
The price is P5,437 per night from 3 Feb to 4 Feb
P5,437
P6,035 total
includes taxes & fees
Feb 3 - Feb 4
9.2/10 Wonderful! (1,002 reviews)
"Rooms were great. Staff was helpful. Was in a perfect spot. Will be back!"

Reviewed on Jan 26, 2025

Holiday Inn Resort Lake George - Adirondack Area, an IHG hotel
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
3 out of 5
1130 Route 9, Queensbury, NY
Fully refundable
The price is P5,168 per night from 11 Feb to 12 Feb
P5,168
P5,736 total
includes taxes & fees
Feb 11 - Feb 12
9/10 Wonderful! (1,009 reviews)
"Everybody was friendly & wanted to go beyond their duties. The best inclusive breakfast I’ ve ever had."

Reviewed on Jan 30, 2025

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
The Queensbury Hotel
The Queensbury Hotel
3 out of 5
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
The price is P5,998 per night from 2 Feb to 3 Feb
P5,998
P6,657 total
includes taxes & fees
Feb 2 - Feb 3
9/10 Wonderful! (1,213 reviews)
"Great"

Reviewed on Jan 30, 2025

The Queensbury Hotel
See all 1,478 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.