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

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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 ...
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 SAR 1,125 per night from Mar 8 to Mar 9
SAR 1,125
SAR 2,831 total
8 Mar - 9 Mar
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 ...
9.8/10 Exceptional! (111 reviews)
Great house. Great location

Reviewed on 4 January 2026

Eagles Nest at Loon Lake near Gore Mountain
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
Book a stay at this business-friendly hotel in Glens Falls. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the restaurant and the helpful ...
9.2/10 Wonderful! (1,507 reviews)
The room was very clean. Had everything we needed including mini fridge. The walls are very thin. The people in the next room were extremely loud and after 11 pm we finally had to call the front desk to complain. Thank goodness they were only there one night out of three night stay. The food in the ...

Reviewed on 9 February 2026

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The Queensbury Hotel
See all 1,537 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.
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 ...
9.8/10 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 3 January 2026

Unique Adirondack Estate on Hudson River - near Gore Mountain & 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 ...
9.8/10 Exceptional! (111 reviews)
Great house. Great location

Reviewed on 4 January 2026

Eagles Nest at Loon Lake near Gore Mountain
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 ...
8/10 Very Good! (35 reviews)
The house was beautiful and charming and plenty of space. We have no complaints but recommend hand towels in the bathrooms. Probably will look up this place again for a skiing trip this winter.

Reviewed on 10 August 2025

Elizabeth. A Guest House Near Lake George.
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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.

Popular places to visit

Loon 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

Friends Lake

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 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

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