Chestertown Holidays

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Chestertown Holiday

Our pick of the best Chestertown Hotel Deals

Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
The price is NZ$181 per night from 15 Nov to 16 Nov
NZ$181
15 Nov - 16 Nov
includes taxes & fees
8.8/10 Excellent! (139 reviews)
"Such a nice place to stay at definitely want to stay there again. Me and my husband went for our honeymoon and the room was super nice and the staff was nice and helpful when we had questions also about the area. The free breakfast that was included was also super delicious. If ur looking for a cozy ..."

Reviewed on 12 Nov 2026

Friends Lake Inn
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
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Pine Tree Motel & Cabins
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Chestertown NY
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Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.
See all 1,625 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.

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.
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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.