Photo by Julie Miller

Find kid-friendly hotels & resorts in Chestertown, NY from $205

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Check availability on Chestertown Family Hotels

This weekend
Next weekend

Compare Chestertown Family Hotels room rates, reviews, and availability. Most hotels are fully refundable.

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (126)
"very friendly and helpful owners. rooms were very clean and comfortable. good location as well"
The price is $205
includes taxes & fees
$185 per night
May 18 - May 19
Pine Tree Motel & Cabins

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (89)
"Quiet, comfortable bed, very clean. Decorated nicely, very cozy feeling. Nice continental breakfast in bright cheery sunroom. Great hiking nearby. Staff responsive to questions and had good recommendations for dining and hiking. Very responsive via text prior to stay even had hiking trail directions printed out for us prior to our arrival. Overall very enjoyable stay. Everything was perfect!"
The price is $261
includes taxes & fees
$235 per night
May 2 - May 3
Friends Lake Inn

Lily Pad South at Loon Lake near Gore Mountain

9.8 out of 10, Exceptional, (47)
"The property was very clean and well supplied. We used it as our home base to snow tube nearby. "
Lily Pad South at Loon Lake near Gore Mountain

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (45)
"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 price is $579
includes taxes & fees
$521 per night
May 12 - May 13
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.
Don't see what you're looking for?
See all available properties in Chestertown

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, Seagle Music Colony, and Blue Line Outdoor Center. Make sure you have lots of time for activities like Up Yonda Farm Environmental Education Center and Tannery Pond Community Center.