Chestertown, NY

Travel Guide

Aerial view of Hudson River in upstate New York, Chestertown, Riparius Bridge. July 12, 2022
Aerial view of Hudson River in upstate New York, Chestertown, Riparius Bridge. July 12, 2022
A winter scene

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
The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
Book a stay at this beach B&B in Chestertown. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Friends Lake and Loon Lake Beach are located ...
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
Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Chestertown NY
The price is ¥46,353 per night from Mar 8 to Mar 9
¥46,353
¥116,624 total
Mar 8 - Mar 9
includes taxes & fees
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 ...
10/10 Exceptional! (115 reviews)
Great house. Great location

Reviewed on Jan 4, 2026

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
The price is ¥22,195 per night from Mar 8 to Mar 9
¥22,195
¥24,635 total
Mar 8 - Mar 9
includes taxes & 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! (1,521 reviews)
Front desk staff upon arrival were great. The staff member I worked with helped us get a room upgrade for a small upcharge. Totally worth it.

Reviewed on Feb 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.
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! (73 reviews)
Excellent stocked kitchen, warm fireplace. Spotlessly cleaned. We loved it! Had everything we could have possibly needed. Warm, comfortable, and beautiful scenery.

Reviewed on Jan 3, 2026

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George
Elizabeth. A Guest House Near Lake George.

Elizabeth. A Guest House Near Lake George.

Chestertown NY
Stay at this vacation home in Chestertown. Enjoy free WiFi, private pools, and a water park. Popular attractions Loon Lake Beach and Friends Lake are located ...
Elizabeth. A Guest House Near Lake George.
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 ...
10/10 Exceptional! (115 reviews)
Great house. Great location

Reviewed on Jan 4, 2026

Eagles Nest at Loon Lake near Gore Mountain
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

Reviews of Chestertown

4.3
Top Destination
5 - Excellent
4
5 - Excellent 44%
4 - Good
4
4 - Good 44%
3 - Okay
1
3 - Okay 11%
2 - Disappointing
0
2 - Disappointing 0%
1 - Terrible
0
1 - Terrible 0%

5/5 - Excellent

Verified traveler

Very quiet and relaxing.

4/5 - Good

Verified traveler

Love the hiking.

5/5 - Excellent

JoeGould

We will definitely be coming back in the spring!

5/5 - Excellent

Batt

Adorable village

Cities near Chestertown