Chestertown, NY

Travel Guide

A waterfront town with a pier, dock, and several buildings.
A red bridge over a river with houses and greenery on both sides.
A snowy lodge with cabins and tall pine trees.

Where to stay in Chestertown

Find the best Chestertown areas and neighborhoods for the activities you enjoy most. Learn more about Chestertown
Learn more about Chestertown

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.

Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

Chestertown NY
Stay at this condo in Chestertown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
9.4/10 Exceptional! (26 reviews)
"Place was really nice and clean. Not far from anywhere so easy to get to and travel around the area. We really enjoyed our stay and would definitely recommend this to my friends and family."

Reviewed on Jul 26, 2026

Peaceful Lakeside Retreat with Private Beach
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
$134 nightly
The price is $149 total per night from Sep 7 to Sep 8
$149 total
Sep 7 - Sep 8
Total with taxes and fees
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 ...
9.4/10 Exceptional! (1,646 reviews)
"Great location and extremely comfortable bed!"

Reviewed on Aug 8, 2026

The Queensbury Hotel
La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George

3 out of 5
1533 US-9 Lake George NY
$101 nightly
The price is $112 total per night from Aug 31 to Sep 1
$112 total
Aug 31 - Sep 1
Total with taxes and fees
Book a stay at this family-friendly hotel in Lake George. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in ...
La Quinta Inn & Suites by Wyndham 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.
Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

Chestertown NY
Stay at this condo in Chestertown. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
9.4/10 Exceptional! (26 reviews)
"Place was really nice and clean. Not far from anywhere so easy to get to and travel around the area. We really enjoyed our stay and would definitely recommend this to my friends and family."

Reviewed on Jul 26, 2026

Peaceful Lakeside Retreat with Private Beach
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! (121 reviews)
"We are a family of 17 and we spent our annual vacation at Eagles Nest. It's centrally located, a reasonable distance from several attractions. The home was perfect for us with plenty of room for everyone and we had a memorable week. Upon arrival, the home was very clean. Cheri (the owner) is excellent ..."

Reviewed on Jul 18, 2026

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 ...
9.6/10 Exceptional! (8 reviews)
"The property was just as described. Clean, comfortable and relaxing. The kitchen had everything I needed and the beds were so comfortable. The grounds were well kept and the lake is beautiful. Several times I was visited by a Doe and her twin fawns! The Loons calling and the crazy Red Squirrels made ..."

Reviewed on Aug 1, 2026

Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.
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.

Stay near popular Chestertown attractions

Cities near Chestertown

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