Chestertown Holiday Packages

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Chestertown Accommodation

If you're after accommodations in Chestertown, make sure you get a move on to book a place to stay. There are only 3 for you to pick from.

Silky smooth sheets, fluffy bathrobes and quality service — if this sounds like your idea of perfection, why not reserve a room at the Friends Lake Inn (963 Friends Lake Rd)? Alternatively, take a look at the Pine Tree Motel & Cabins (5537 State Route 8). It's an excellent option if you're searching for a place that's comfortable and affordable.

Car Hire in Chestertown

While it's not possible to rent a car directly at Floyd Bennett Memorial Airport, Hertz is only a short cab journey away. Located at 674 Quaker Road, you can get a hold of those keys and drive off into the distance soon after you hit the tarmac.

Holidays to Chestertown

Stuck at work fantasising about Chestertown and all the exciting things it has to offer? Take the first step to actually getting there by finding out a few basic facts about it.

Chestertown is 40 kilometres north of Glens Falls. From the nation's capital, Washington, the town is 590 kilometres to the northeast.

Around about 700 people call this part of New York home. So, if you're hoping to meet some new pals, you shouldn't have too many problems.

Top Chestertown hotels

The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
The Fern Lodge: Beach bed & breakfast with free breakfast and free WiFi. Located in the mountains.
I cannot say enough good things about the Fern Lodge. Beautiful atmosphere, wonderful host. Will be returning!

Reviewed on 27 Dec 2025

Opens in a new windowThe Fern Lodge
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
Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.: Pet-friendly ...
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 25 Mar 2026

Opens in a new windowLakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown NY
Eagles Nest at Loon Lake near Gore Mountain: Family-friendly holiday home with WiFi and parking. Located on a lake.
Opens in a new windowEagles Nest at Loon Lake near Gore Mountain
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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.