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.

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.

Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
The price is £75 per night from 16 Nov to 17 Nov
£75
16 Nov - 17 Nov
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located ...
8.6/10 Excellent! (138 reviews)
"Amazing Room"

Reviewed on 8 Nov 2026

Friends Lake Inn
Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
Stay at this motel in Chestertown. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located ...
Pine Tree Motel & Cabins
Elizabeth. 15 minutes to Lake George.
Seasonal Heated Pool.

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Chestertown NY
Stay at this holiday home in Chestertown. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Loon Lake Beach and Friends Lake are located ...
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.
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.
Elizabeth. 15 minutes to Lake George.
Seasonal Heated Pool.

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Chestertown NY
Stay at this holiday home in Chestertown. Enjoy free Wi-Fi, private pools and a garden. Popular attractions Loon Lake Beach and Friends Lake are located ...
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.
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 ...
Eagles Nest at Loon Lake near Gore Mountain
Lincoln Log Colony

Lincoln Log Colony

2 out of 5
2180 U.S. 9 Lake George NY
Stay at this cabin in Lake George. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Great Escape and Pirate's Cove Adventure Golf of Lake ...
Lincoln Log Colony
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