Chestertown Vacations from $1,143

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Your Chestertown Vacation

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 vacation 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 vacation is only a few clicks away with Expedia.

The Latest Chestertown vacation packages

Price found within the past 48 hours. Click for updated prices.
Llama House ADK

Llama House ADK

2.5 out of 5
Price was $1,374, price is now $1,143 per person
$1,143
per person
Jun 25 - Jul 2
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
9.2/10 Wonderful! (34 reviews)
Dave was very considerate, enjoyed our stay

Reviewed on Feb 6, 2026

The Queensbury Hotel

The Queensbury Hotel

3 out of 5
Price was $1,656, price is now $1,276 per person
$1,276
per person
Jun 25 - Jul 2
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
9.4/10 Exceptional! (1,549 reviews)
Great property, celebrating 100 year anniversary. Solid, comfortable, tastefully updated!

Reviewed on Mar 27, 2026

The Alpine Lodge

The Alpine Lodge

3 out of 5
Price was $1,676, price is now $1,307 per person
$1,307
per person
Jun 25 - Jul 2
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
9/10 Wonderful! (675 reviews)
When I checked in, the front desk helped me resolve an issue with my reservation made through Expedia. However, I was told over the phone before my arrival that breakfast was included, but it turned out breakfast is only served on weekends. Due to this discrepancy, I cannot give a 5-star rating.

Reviewed on Mar 7, 2026

Twister 68a-i 4 Bedroom Townhouse

Twister 68a-i 4 Bedroom Townhouse

3 out of 5
Price was $5,095, price is now $4,381 per person
$4,381
per person
Jun 25 - Jul 2
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
No reviews
North Creek Lodge at Gore Mountain

North Creek Lodge at Gore Mountain

3 out of 5
Price was $1,419, price is now $1,226 per person
$1,226
per person
Jun 25 - Jul 2
found 3 hours ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
7.8/10 Good! (445 reviews)
Super friendly staff, tasty food, very cool lodge atmosphere. The room was warm and clean, the bed was soft. Happy hour and dinner in a lodge was the highlight of the stay. Laughing with the chef and enjoying his food. I would stay there again.

Reviewed on Mar 9, 2026

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Discover the most popular places to visit in Chestertown

Loon Lake Beach

If a restful vacation is part of your travel plans, Loon Lake Beach might be the perfect place to seek out during your trip to Chestertown. While you're in the area, stroll along the lakeside.

Loon Lake Beach

Chestertown Hotel Deals

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown NY
Get rates
Eagles Nest at Loon Lake near Gore Mountain
Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.

Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.

Chestertown NY
10/10 Exceptional! (3 reviews)
This was our first vacation rental as we were reluctant to try it after reading horrible stores about hidden fees and a tons of house cleaning list. We took a plunge this time and I am glad we did it. If you cook a lot (not us), a large party (not us), then this is perfect. It was a bit too big for ...

Reviewed on Mar 25, 2026

Get rates
Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.
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
$169 nightly
The price is $188 total per night from Apr 19 to Apr 20
$188 total
Apr 19 - Apr 20
Total with taxes and fees
8/10 Very Good! (1,586 reviews)
Very good

Reviewed on Mar 31, 2026

Six Flags Great Escape Lodge & Indoor Waterpark
See all 1,536 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.

Find the Best Chestertown Vacation Packages

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 2 miles (3 km) from the downtown area.

Chestertown Essential Information

Language
English
Currency
U.S dollars
Population
680
Max Temp Winter
30ºF
Max Temp Summer
75ºF
Top Sights
Gore Mountain Ski Resort, Loon Lake Beach and Natural Stone Bridge and Caves

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Frequently asked questions

How much does a Chestertown vacation package cost?
You can snap up a vacation package to this destination from $1,143 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?
If you're looking to book a cheap Chestertown vacation package, consider visiting in February, November and December. You're likely to find lower rates on hotels and flights during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Chestertown?
The ideal duration of your Chestertown vacation depends on what you'd like to see and do. Usually, a few days to a week will give you enough time to hit all the top sights and explore some hidden gems along the way.
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 heading away with the family or planning a trip 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.
Does Expedia offer Book Now, Pay Later Chestertown vacation packages?
If you're like us, you love going away but don't love the big price tag that can sometimes come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the total cost of your Chestertown trip over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up cheap vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.