Chestertown Vacations from $1,025

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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.
North Creek Lodge at Gore Mountain

North Creek Lodge at Gore Mountain

3 out of 5
Price was $1,058, price is now $1,025 per person
$1,025
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip flight included
Hartford (BDL) to Glens Falls (GFL)
7.8/10 Good! (437 reviews)
Our overnight stay was lovely & fast since we got up pretty early to get to Gore Mtn. early- The breakfast was very nice too, with some fresh fruit, yoghurt, cereal, toast/eggs and other goodies! The staff were very nice too!! 5/5

Reviewed on Mar 3, 2026

Twister 68a-i 4 Bedroom Townhouse

Twister 68a-i 4 Bedroom Townhouse

3 out of 5
Price was $2,767, price is now $2,656 per person
$2,656
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip flight included
Hartford (BDL) to Glens Falls (GFL)
No reviews
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
Price was $1,096, price is now $1,056 per person
$1,056
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip flight included
Hartford (BDL) to Glens Falls (GFL)
9.4/10 Exceptional! (1,526 reviews)
Staff good Room really small Bathroom toliet extremely low to the floor Only 2 plugs in whole room Mattress not comfortable

Reviewed on Mar 2, 2026

The Alpine Lodge

The Alpine Lodge

3 out of 5
Price was $1,086, price is now $1,051 per person
$1,051
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip flight included
Hartford (BDL) to Glens Falls (GFL)
9/10 Wonderful! (670 reviews)
Very comfortable and accessible to Gore Mt. Have stayed here many times- after a long, hard winter I think in need of a deep clean though. Very sad the fantastic food venues in North Creek are gone! Hoping next year brings new restaurant venues. It’s a great little town and Alpine Lodge is very convenient, safe and affordable.

Reviewed on Mar 5, 2026

Rumor 39O - Upgraded Townhome With Woodsy Views 3 Bedroom Townhouse by The Summit at Gore Mountain

Rumor 39O - Upgraded Townhome With Woodsy Views 3 Bedroom Townhouse by The Summit at Gore Mountain

3 out of 5
Price was $1,819, price is now $1,785 per person
$1,785
per person
Apr 23 - Apr 26
found 19 hours ago
Roundtrip flight included
Hartford (BDL) to Glens Falls (GFL)
No reviews
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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

The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
$431 nightly
The price is $479 total per night from Mar 19 to Mar 20
$479 total
Mar 19 - Mar 20
Total with taxes and fees
10/10 Exceptional! (52 reviews)
I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning!

Reviewed on Dec 27, 2025

The Fern Lodge
Secluded and Cozy Lakeside Townhome on Tripp Lake!

Secluded and Cozy Lakeside Townhome on Tripp Lake!

2 out of 5
Chestertown NY
10/10 Exceptional! (2 reviews)
The host, Bryce, responded in a quick manner whenever we reached out to him. The accommodations were homey, spacious, and it was a quick and easy walk from the parking space to the place. Would definitely stay there again.

Reviewed on Feb 8, 2026

Get rates
Secluded and Cozy Lakeside Townhome on Tripp Lake!
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown NY
$629 nightly
The price is $698 total per night from Mar 8 to Mar 9
$698 total
Mar 8 - Mar 9
Total with taxes and fees
10/10 Exceptional! (115 reviews)
Great house. Great location

Reviewed on Jan 4, 2026

Eagles Nest at Loon Lake near Gore Mountain
See all 1,523 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 $1,025 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.