Chestertown Vacations

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Find the Best Chestertown Vacation Packages

Chestertown Hotel Deals

The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
9.8/10 Exceptional! (47 reviews)
I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning!

Reviewed on 27 December 2025

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The Fern Lodge
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown NY
The price is AED 1,102 per night from Feb 4 to Feb 5
AED 1,102
AED 2,797 total
4 Feb - 5 Feb
includes taxes & fees
9.8/10 Exceptional! (111 reviews)
the kitchen was good, adequate space for people to work.no lake viewbeds were comfortable

Reviewed on 7 October 2025

Eagles Nest at Loon Lake near Gore Mountain
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
7.8/10 Good! (1,471 reviews)
Room accommodation was good and staff were approachable and helpful.

Reviewed on 9 January 2026

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Six Flags Great Escape Lodge & Indoor Waterpark
See all 1,539 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.

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

Frequently asked questions

How do I find cheap flights to Chestertown that have flexible change policies?
At Expedia, we've been channeling our inner Olympic gymnast to get you the most flexible fares in town. Simply click on "No change fee" under the "Flexible change policies" heading to find the best flights to Chestertown.
Which airlines fly to Chestertown?
Heading to Chestertown is as simple as deciding between two well-known carriers. Book your airfare with one of the following:

  • American Airlines - 394 flights to or near Chestertown each month, including 394 flights to Albany Intl. Airport (ALB) per month.
  • United Airlines - 229 flights to or near Chestertown each month, including 229 flights to Albany Intl. Airport (ALB) per month.

How can I find cheap tickets to Chestertown?
In the last seven days, was the best price for a flight to Chestertown. If you want to save even more, book in advance and be flexible with your dates. Search for your flight to Chestertown, then compare prices for nearby days by clicking on our "flexible dates" link.
How much is a flight to Chestertown?
One-way flights departing from () sold for as little as in the last seven days. During this time, the price of a round-trip fare to Chestertown varied between and . If you find a fantastic deal, book ASAP — these prices don't hang about.
What are the most popular airports to fly into in Chestertown?
Start arranging your Chestertown escape by booking one of the 1,153 flights every month to Albany Intl. Airport (ALB). This is the region's primary gateway.
When is the cheapest time to fly to Chestertown?
Leave for Chestertown early in the week and you'll usually be rewarded with more affordable fares. Tuesday is typically the cheapest day to hop on a plane, followed by Monday. If you'd like to avoid the most expensive flights, keep clear of Saturdays.
How much is a plane ticket to Chestertown?
In the last seven days, plane fares to Chestertown fluctuated between and . The early bird catches the worm, so book a good deal today.
What months are the cheapest to book a flight to Chestertown?
A great month to book low-cost fares to Chestertown is February. It's worth noting that in the United States, an expensive time to purchase a ticket is during the festive month of December.
How long is a flight to Chestertown?
It could take you an hour or more — it really depends on which part of the U.S. You're coming from. The average flight times for these in-demand domestic routes to Chestertown will give you a rough idea of what you can expect:

  • Chicago, IL (ORD-O'Hare Intl.) to Albany Intl. Airport (ALB) - 2 hours and 8 minutes
  • Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) to Albany Intl. Airport (ALB) - 1 hour and 14 minutes
  • Charlotte, NC (CLT-Charlotte-Douglas Intl.) to Albany Intl. Airport (ALB) - 1 hour and 54 minutes