Chestertown, NY

Travel Guide

Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA
Aerial view of Hudson River in upstate New York, Chestertown, Riparius Bridge. July 12, 2022
Chestertown

Where to stay in Chestertown

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Chester Shores

When in Chester Shores, you can plan a visit to Loon Lake Beach and Loon Lake, some noteworthy sights in the nearby area.

Chester Shores
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown NY
Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ...
Eagles Nest at Loon Lake near Gore Mountain
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
Stay at this vacation home in Chestertown. Enjoy free WiFi, tennis courts, and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
10/10 Exceptional! (3 reviews)
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 Mar 25, 2026

Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.
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
$169 nightly
The price is $188 total per night from Apr 19 to Apr 20
$188 total
Apr 19 - Apr 20
Total with taxes and fees
Book a stay at this family-friendly resort in Queensbury. Enjoy free WiFi, free parking, and 3 restaurants. Our guests praise the breakfast and the helpful staff ...
8/10 Very Good! (1,610 reviews)
Pool area is fun, but other amenities and activities are lack luster

Reviewed on Apr 11, 2026

Six Flags Great Escape Lodge & Indoor Waterpark
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.
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
Stay at this vacation home in Chestertown. Enjoy free WiFi, tennis courts, and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
10/10 Exceptional! (3 reviews)
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 Mar 25, 2026

Lakefront 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
Book a stay at this family-friendly vacation home in Chestertown. Enjoy a garden, laundry facilities, and a pool table. Popular attractions Loon Lake and Loon ...
Eagles Nest at Loon Lake near Gore Mountain
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Chestertown NY
Stay at this apartment in Chestertown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Friends Lake and Tripp Pond are located ...
10/10 Exceptional! (76 reviews)
Hosts on location are very friendly and go above and beyond to make the stay enjoyable . The girls love playing with the dogs pearl and ruby. Been coming for several years and plan to return.

Reviewed on Feb 18, 2026

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
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.

Popular places to visit

Cities near Chestertown

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