Chestertown Vacations

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Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

Eagles Nest at Loon Lake near Gore Mountain
Eagles Nest at Loon Lake near Gore Mountain
Chestertown
9.8/10 Exceptional! (104 reviews)
Gore ski vacation with friends
"Well-appointed house, very clean, well-equipped kitchen, host was easy to contact and attentive, steep driveway but was cleared very well, enough parking, game room was nice surprise, downstairs beds were on the small size, grounds were snow covered but appeared to be nicely landscaped and cared ..."

Reviewed on 16 March 2025

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Eagles Nest at Loon Lake near Gore Mountain
The Queensbury Hotel
The Queensbury Hotel
3 out of 5
88 Ridge St, Glens Falls, NY
Fully refundableReserve now, pay when you stay
The price is AED 410 per night from Apr 3 to Apr 4
AED 410
AED 455 total
includes taxes & fees
3 Apr - 4 Apr
9.2/10 Wonderful! (1,249 reviews)
One of the best hotels
"Always an amazing stay at this historic hotel in the quaint town of Glen Falls. Everything in walking distance."

Reviewed on 27 March 2025

The Queensbury Hotel
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
The price is AED 569 per night from Apr 27 to Apr 28
AED 569
AED 794 total
includes taxes & fees
27 Apr - 28 Apr
7.6/10 Good! (1,100 reviews)
"Amazing stay and staff"

Reviewed on 22 March 2025

Six Flags Great Escape Lodge & Indoor Waterpark
See all 1,468 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 vacation package cost?
You can snap up a vacation package to this destination 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?
To score cheap Chestertown vacation packages, organize 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 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.
How to plan a trip to Chestertown?

  1. Pick your dates: What you’d like to do in Chestertown and your favorite 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 accommodations and airfare: After you’ve nailed down your trip dates and duration, lock in the ideal Chestertown vacation package for you.

Discover the most popular places to visit in Chestertown

Friends Lake

5/5(3 reviews)

Commune with nature and explore the great outdoors at Friends Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

Friends Lake

Loon Lake

Commune with nature and explore the great outdoors at Loon Lake during your travels in Chestertown. While you're in the area, stroll along the lakeside.

Loon Lake

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