Chestertown Holidays

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Top hotels in Chestertown

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
9.2/10 Wonderful! (146 reviews)
We attended the Warrensburg Largest Garage Sale Weekend. The Motel is only 20 minutes away from the event. Located near Chestertown so you can go out to eat or grab groceries at the local Grocery Store. Motel is Dog Friendly and we did not have any issues with the Wi-Fi.

Reviewed on 5 Oct 2025

Pine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
8.6/10 Excellent! (102 reviews)
Staff was great. The inn is unique. Perfect!

Reviewed on 7 Sept 2025

Friends Lake Inn
The Queensbury Hotel

The Queensbury Hotel

3 out of 5
88 Ridge St Glens Falls NY
Fully refundableReserve now, pay when you stay
9.2/10 Wonderful! (1,423 reviews)
Clean room & friendly staff.

Reviewed on 13 Nov 2025

The Queensbury Hotel
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.