Chestertown Holidays

Book a Hotel + Flight or Car together to unlock savings

Photo by Julie Miller

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 4.566.625 ₫ per night from 29 Jun to 30 Jun
4.566.625 ₫
5.068.954 ₫ total
29 Jun - 30 Jun
includes taxes & fees
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"

Reviewed on 28 Oct 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 27 Aug 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! (1,247 reviews)
"Nice historic hotel in great location. Good in-house restaurant/bar with live music & good food. Breakfast is also outstanding in the larger dining area"

Reviewed on 23 Jun 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 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.