Chestertown Vacations from $604

Book a Hotel + Flight or Car together to unlock savings

Photo by Julie Miller

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.
Days Inn by Wyndham Queensbury/Lake George

Days Inn by Wyndham Queensbury/Lake George

2 out of 5
Price was $720, price is now $604 per person
$604
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
5.8/10 (1,009 reviews)
Hotel was fine. Room price per night was very reasonable. Everything in our room working properly. Other guests were making petty complaints to the front desk. Holding up the check in line. If they wanted a 5 star room then they should have booked a 5 star hotel. It was a nice stay.

Reviewed on Aug 18, 2025

Llama House ADK

Llama House ADK

2.5 out of 5
Price was $1,089, price is now $846 per person
$846
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
9/10 Wonderful! (29 reviews)
Very welcoming lodge vib- an opportunity to connect with other hikers. The bed was very comfortable and the nice hot shower really made my day. Wilson, the dog, is a gem.

Reviewed on Aug 10, 2025

The Alpine Lodge

The Alpine Lodge

3 out of 5
Price was $1,171, price is now $912 per person
$912
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
9/10 Wonderful! (634 reviews)
Wonderful stay in North Creek. Great access to local shops and easy to get to great hiking. Clean quiet and, safe.

Reviewed on Aug 25, 2025

The Fern Lodge

The Fern Lodge

3.5 out of 5
Price was $1,128, price is now $996 per person
$996
per person
Oct 7 - Oct 9
found 9 hours ago
Roundtrip flight included
New York (NYC) to Glens Falls (GFL)
9.8/10 Exceptional! (47 reviews)
Paradise just simply heavenly. And so well appointed. Feel so at home

Reviewed on Oct 15, 2023

Holiday Inn Express Queensbury - Lake George Area by IHG

Holiday Inn Express Queensbury - Lake George Area by IHG

2.5 out of 5
Price was $1,111, price is now $981 per person
$981
per person
Oct 1 - Oct 8
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Glens Falls (GFL)
9/10 Wonderful! (1,002 reviews)
Very nice hotel all around.

Reviewed on Aug 11, 2025

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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

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8, Chestertown, NY
$175 nightly
The price is $194 total per night from Aug 27 to Aug 28
$194 total
Aug 27 - Aug 28
Total with taxes and fees
9.2/10 Wonderful! (135 reviews)
"Bed was comfortable, and plenty big for 2."

Reviewed on Aug 13, 2025

Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd, Chestertown, NY
$223 nightly
The price is $248 total per night from Aug 27 to Aug 28
$248 total
Aug 27 - Aug 28
Total with taxes and fees
8.6/10 Excellent! (98 reviews)
"Beautiful setting. Very clean. Charming building. Friendly staff. Breakfast included."

Reviewed on Aug 17, 2025

Friends Lake Inn
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St, Glens Falls, NY
$134 nightly
The price is $149 total per night from Sep 8 to Sep 9
$149 total
Sep 8 - Sep 9
Total with taxes and fees
9.2/10 Wonderful! (1,329 reviews)
"Historic property in the middle of downtown glens falls and 20-25 min from the track great place to go to after take a little swim then 20 min in the hot tub and after there's food and drinks at two places on site or room service you may get a 20 $ room credit depending on how you book it like if ..."

Reviewed on Aug 24, 2025

The Queensbury Hotel
See all 1,552 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.

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.

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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 $604 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.