Chestertown

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.

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.
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
The price is CA $163 per night from Nov 9 to Nov 10
CA $163
CA $181 total
Nov 9 - Nov 10
includes taxes & fees
Stay at this hotel in Chestertown. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Friends Lake and Loon Lake Beach are located ...
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 WiFi, free parking, and a 24-hour front desk. Popular attractions Loon Lake Beach and Loon Lake are located ...
Get rates
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 vacation home in Chestertown. Enjoy free WiFi, private pools, and a garden. Popular attractions Loon Lake Beach and Friends Lake are located ...
Get rates
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.
See all 1,624 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.
Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

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

Chestertown NY
Stay at this vacation home in Chestertown. Enjoy free WiFi, 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
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 ...
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 WiFi, free parking, and an outdoor pool. Popular attractions Great Escape and Pirate's Cove Adventure Golf of Lake ...
Lincoln Log Colony
See all 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.

Stay near popular Chestertown attractions

Loon Lake

8.8/10 (8 reviews)
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.
See properties

Cities near Chestertown

An aerial view of a small island with dense forests, a large white mansion, and a dock with boats.

Bolton Landing

A calm lake surrounded by dense forests with autumn foliage, under a cloudy sky.

Diamond Point

A mountainous landscape with dense forests and a visible lake.

Johnsburg

A forest with autumn foliage in shades of orange, yellow, and green.

Pottersville