Chestertown Holidays

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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

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 €109 per night from 30 Apr to 1 May
€109
includes taxes & fees
30 Apr - 1 May
9.2/10 Wonderful! (1,239 reviews)
"Historic hotel lovingly renovated. Wonderful service."

Reviewed on 27 Apr 2025

The Queensbury Hotel
Six Flags Great Escape Lodge & Indoor Waterpark
Six Flags Great Escape Lodge & Indoor Waterpark
3.5 out of 5
89 Six Flags Dr, Queensbury, NY
The price is €100 per night from 19 May to 20 May
€100
includes taxes & fees
19 May - 20 May
7.6/10 Good! (1,105 reviews)
"Water park"

Reviewed on 25 Apr 2025

Six Flags Great Escape Lodge & Indoor Waterpark
Walk to Million Dollar Beach from this awesome Cottage!
Walk to Million Dollar Beach from this awesome Cottage!
Lake George
9.8/10 Exceptional! (151 reviews)
Perfect!
"This is our third time staying at this property. Each and every time, I am so sad to leave. The hosts are fantastic and answer promptly any questions we may have. This property is so beautiful and we can't wait to come back again next spring."

Reviewed on 28 Oct 2024

Get rates
Walk to Million Dollar Beach from this awesome Cottage!
See all 1,425 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 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?

  1. Pick your dates: What you’d like to do in Chestertown and your favourite 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 accommodation and airfare: After you’ve nailed down your trip dates and duration, lock in the ideal Chestertown holiday package for you.

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