Chestertown , NY Pet Friendly Hotels

Name: Pine Tree Motel & Cabins
Rating: 9.2

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Top Chestertown Pet Friendly Hotels

Pine Tree Motel & Cabins

5537 State Route 8 Chestertown NY

This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a picnic area, and express check-in are also on offer.

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 Oct 5, 2025

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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.

Pet owners shouldn't miss Chestertown, a city known for its canoeing, and sights like Loon Lake Beach and Pack Demonstration Forest.

How to Wander Wisely in Chestertown with Your Pet

Enjoy top attractions like Natural Stone Bridge and Caves, Tannery Pond Community Center, and North Creek Ski Bowl Town Park.
Other things to see include Gore Mountain Ski Resort, North Creek Depot Museum, and Up Yonda Farm Environmental Education Center.

Top Pet-Friendly Hotels in Chestertown

Pine Tree Motel & Cabins
Pets are allowed for a fee at this 2-star motel, although restrictions apply. Guests appreciate its location.

Pet-Friendly Times to Vacation in Chestertown

Weather can make or break your stay, especially if you want to spend time wandering around the city. Here are the average temperatures to help plan your vacation in Chestertown.

From January to March, average temperatures range from 49°F in the daytime to 6°F at night. Between April and June, the daytime average is 80°F and the nighttime average is 27°F.

From July to September, average temperatures range from 81°F in the daytime to 40°F at night. Between October and December, the daytime average is 64°F and the nighttime average is 10°F.