Photo by Julie Miller

Family friendly Hotels in Chestertown, New York

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family friendly Hotels

Top Chestertown Family friendly Hotels

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (128)
"Excellent location and staff was very friendly."
The price is P9,885
P10,972 total
includes taxes & fees
Jul 15 - Jul 16
Pine Tree Motel & Cabins

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
The price is P12,598
P13,983 total
includes taxes & fees
Jul 15 - Jul 16
Friends Lake Inn

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"We had such a great experience the first night so we moved our plans and stayed a second, next time we will definitely stay even longer."
The Fern Lodge
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.

Frequently asked questions

What's Chestertown like for family-friendly vacations?
You might want to consider the remote destination of Chestertown if you've been thinking about a trip for the whole family. The boating, horseback riding, and canoeing are just a few things that make this an attractive vacation spot for families. Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) from the city center.
What's the best place to stay when traveling with kids to Chestertown?
Pine Tree Motel & Cabins is a property with free parking and free WiFi, and it's a top choice on Expedia for families. The Fern Lodge is another good option for your family trip.
How many family-friendly hotels will I be able to find in Chestertown?
Expedia has 18 hotels in Chestertown that are great for families.
When's the best time to book a family-friendly vacation in Chestertown?
The hottest months are usually July and August with an average temp of 65°F, while the coldest months are January and February with an average of 25°F. The snowiest months in Chestertown are January, March, November, and December, with each month seeing an average of 13 inches of snowfall.
What's there to see and do with your family in Chestertown?
While you are visiting Chestertown, you and the family might want to check out some interesting spots such as Gore Mountain Ski Resort, Blue Line Outdoor Center, and Up Yonda Farm Environmental Education Center. Make sure you have lots of time for activities like Tannery Pond Community Center and The Sembrich.