Photo by Julie Miller

Find Family Hotels in Chestertown, NY

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

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

Pine Tree Motel & Cabins
Exterior

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"
Pine Tree Motel & Cabins
Friends Lake Inn
Property entrance

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (84)
"Great room, very nice staff. Nice weekend getaway."
The price is SAR 837
SAR 929 total
includes taxes & fees
26 Dec - 27 Dec
Friends Lake Inn
Lily Pad South at Loon Lake near Gore Mountain
A restful sleep in the "Wild Flower" is awaiting your arrival.

Lily Pad South at Loon Lake near Gore Mountain

9.8 out of 10, Exceptional, (44)
"Whenever im in the adirondacks I stay at The Lilly Pad. Super comfortable beds. Gracious host who will go out of her way to help you! I plan to stay here for all my future trips to the area. "
Lily Pad South at Loon Lake near Gore Mountain
The Fern Lodge
Room

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 SAR 2,249
SAR 2,496 total
includes taxes & fees
6 Jan - 7 January 2025
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.
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 Hickory Ski Center. Make sure you have lots of time for activities like Blue Line Outdoor Center and Up Yonda Farm Environmental Education Center.