Chestertown Holidays
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- Rest easyPackages with flights are ATOL protected
Your Chestertown Holiday
There's plenty to like about Chestertown, from its rich history to its spectacular views. When you're ready to spend a bit of time in this interesting city, our Chestertown holiday packages will be ideal for you. Friends Lake, Loon Lake and Loon Lake Beach are just a few of the sights you'll want to see during your trip to Chestertown. Don't put off your visit to this destination any longer. Your dream Chestertown holiday is only a few clicks away with Expedia.
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 2 miles from the downtown area.
Chestertown Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Population | 680 |
Max Temp Winter | -1.11ºC |
Max Temp Summer | 24ºC |
Top Sights | Gore Mountain Ski Resort, Loon Lake Beach and Natural Stone Bridge and Caves |
Top hotels in Chestertown
Peaceful Lakeside Retreat with Private Beach
Chestertown NY
9.4/10 Exceptional! (26 reviews)
"Place was really nice and clean. Not far from anywhere so easy to get to and travel around the area. We really enjoyed our stay and would definitely recommend this to my friends and family."
Reviewed on 26 Jul 2026
The Queensbury Hotel
88 Ridge St Glens Falls NY
Fully refundableReserve now, pay when you stay
£99
7 Sept - 8 Sept
includes taxes & fees
9.4/10 Exceptional! (1,655 reviews)
"Adorable hotel with tons of history!"
Reviewed on 12 Aug 2026
La Quinta Inn & Suites by Wyndham Lake George
1533 US-9 Lake George NY
Fully refundableReserve now, pay when you stay
£83
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,697 reviews)
"Great place to stay. Highly recommended with kids."
Reviewed on 12 Aug 2026
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.
Friends Lake
9.4/10 (14 reviews)
This private Adirondack gem offers pristine waters and tranquil surroundings away from tourist crowds. Stay at Friends Lake Inn to access swimming, fishing, and kayaking in this exclusive 450-acre natural retreat.
Loon Lake Beach
8.4/10 (7 reviews)
Loon Lake Beach offers crystal-clear waters against the backdrop of the Adirondack Mountains. Enjoy a day of swimming and picnicking in this serene natural setting, where sandy shores meet lush greenery.
Tripp Pond
8.6/10 (4 reviews)
Tripp Pond offers a tranquil escape with calm waters surrounded by lush forests in Chestertown, New York. Enjoy peaceful fishing or kayaking while taking in the natural beauty of the Adirondack landscape.
Frequently asked questions
How much does a Chestertown travel package cost?
Maybe less than you might think — from only , as a matter of fact! By bundling hotels, flights and car rentals into your own customized travel package, your trip to Chestertown is just a few clicks away.
If I'm not able to travel, can I cancel my Chestertown travel package?
Your situation can change without warning, so yes, you can. You may be able to change or cancel your Chestertown travel package for free if you've booked in the last 24 hours. For older bookings, you can still make the necessary changes, but your airline, hotel or car rental company may charge a fee. Need more information? Visit our Customer Service Portal. We're here to help make sure your trip goes off without a hitch.
How do I get a cheap travel package to Chestertown?
Bundle your flights and hotels with Expedia to save on your next adventure. With more than 550 air carriers and 1,000,000 hotel options around the globe, your Chestertown travel package can be customized exactly to suit your budget. With all that extra cash, why not add one or two awesome activities and tours? It's an easy way to unlock even more savings. That dream holiday to Chestertown is closer than you thought!
Does Expedia offer Book Now, Pay Later Chestertown holidays?
Expedia has joined forces with online lender Klarna to make booking your next break a little easier on the wallet. Paying by instalment means you can spread the costs of your next adventure, leaving you with more cash to play with while you're travelling. Klarna has several payment plans to pick from, so you're sure to find something that falls within your budget. Consider these flexible payment options:
- Pay monthly holidays: If paying small amounts each month is what works best for you, Klarna can help. Paying in convenient monthly instalments will make your holiday dreams possible.
- Pay in instalments holidays: If you'd like to pay off your escape in multiple transactions, holidays paid in instalments might be the right choice for your Book Now, Pay Later holiday through Klarna.
- Low deposit holidays: If paying a small percentage of your getaway (rather than the total upfront) makes it easier to click that "book now" button, go for a low deposit holiday payment plan with Klarna.
Where should I stay in Chestertown?
Stay where the action is. Many visitors favor hotels in the vicinity of top sights, like Friends Lake, Loon Lake and Loon Lake Beach.
What are the top hotels in Chestertown?
If it's your first time staying in Chestertown, reserve a room at Super 8 by Wyndham Lake George/Warrensburg Area or Courtyard by Marriott Lake George. Both will make you feel at home and are top options with lots of travellers.
How far in advance should I book my Chestertown holiday?
It's always wise to book early. Air carriers typically release flights up to 12 months ahead of departure, and this is when you can land some rock-bottom prices. Just been told you need to take some holiday time in a few weeks? No problem! Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at a price you can afford.
What does an Expedia Chestertown travel package include?
Packages include rental cars, hotels and flights, but you can combine any of them to create your perfect Chestertown trip. You can also add on fun stuff like activities and tours once you've made your booking. You're in control! When you bundle your bookings with Expedia, you'll get discounts you won't find elsewhere.
What should I know before booking a Chestertown travel package?
A travel package can be cheaper than individually booking all you need for your getaway. For example, bundle your flights, hotels and rental cars and score big savings. Whatever type of holiday you have in mind, there's sure to be a package that's right for you.
Can I choose my airline with a Chestertown Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines worldwide. Our packages give you the freedom to take your pick of available flights, hotels and activities that fit your needs.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.
