Chestertown Travel Guide

Tourist 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.

Our guide on where to stay in Chestertown

Find the best Chestertown areas for the activities you enjoy most.

Chester Shores

While Chester Shores isn't home to many top sights, Loon Lake Beach and Loon Lake are some notable places to visit nearby.

Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

Chestertown NY
Stay at this condo in Chestertown. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
9.4/10 Exceptional! (25 reviews)
"This was a great place to stay with our family of 4 in the Adirondacks. The lake was beautiful, and we spent most of our days fishing and swimming there. It is a very quiet community, and the condo was comfortable and well stocked. There is no central air conditioning, but there are 2 mobile units, ..."

Reviewed on 18 July 2026

Peaceful Lakeside Retreat with Private Beach
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
The price is AU$199 per night from 23 Aug to 24 Aug
AU$199
23 Aug - 24 Aug
includes taxes & fees
Stay at this family-friendly hotel in Lake George. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
8.8/10 Excellent! (1,665 reviews)
"The ‘free’ continental breakfast was pitiful! Kept running out of stuff and few tables for seating. The rooms were great!!!"

Reviewed on 23 July 2026

La Quinta Inn & Suites by Wyndham Lake George
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 AU$342 per night from 20 Aug to 21 Aug
AU$342
20 Aug - 21 Aug
includes taxes & fees
Stay at this family-friendly resort in Queensbury. Enjoy free Wi-Fi, free parking and 3 restaurants. Our guests praise the breakfast and the helpful staff in ...
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.
Peaceful Lakeside Retreat with Private Beach

Peaceful Lakeside Retreat with Private Beach

Chestertown NY
Stay at this condo in Chestertown. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
9.4/10 Exceptional! (25 reviews)
"This was a great place to stay with our family of 4 in the Adirondacks. The lake was beautiful, and we spent most of our days fishing and swimming there. It is a very quiet community, and the condo was comfortable and well stocked. There is no central air conditioning, but there are 2 mobile units, ..."

Reviewed on 18 July 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
Stay at this family-friendly holiday home in Chestertown. Enjoy a garden, laundry facilities and a pool table. Popular attractions Loon Lake and Loon Lake Beach ...
10/10 Exceptional! (119 reviews)
"Very lovely property with beautiful views"

Reviewed on 5 July 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 holiday home in Chestertown. Enjoy free Wi-Fi, tennis courts and patios. Popular attractions Tripp Pond and Pack Demonstration Forest are located ...
9.4/10 Exceptional! (6 reviews)
"Great location close enough to all the activities we wanted to do near Lake George, but just far enough out of the hustle and bustle to be relaxing. Great amenities with the beach and ball courts. Plenty of room for our family."

Reviewed on 23 July 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