Photo by Julie Miller

Find Family Hotels in Chestertown, NY

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Check availability on Chestertown Family Hotels

Tonight
1 Feb - 2 Feb
Tomorrow
2 Feb - 3 Feb
Next weekend
7 Feb - 9 Feb
In two weeks
14 Feb - 16 Feb

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, (86)
"Quiet lodging and friendly staff"
The price is AED 819
AED 909 total
includes taxes & fees
2 Feb - 3 Feb
Friends Lake Inn
Lily Pad South at Loon Lake near Gore Mountain

Lily Pad South at Loon Lake near Gore Mountain

9.8 out of 10, Exceptional, (44)
"Very clean, comfortable, kitchen is well stocked with cookware & spices, lots of towels & crisp fresh sheets. 2 nice restaurants (Bull house & OP Fredericks) are within a few minutes drive. There is a LOT of outdoor firewood & we enjoyed relaxing by the fire pit."
The price is AED 309
AED 802 total
includes taxes & fees
5 Feb - 6 Feb
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 AED 2,090
AED 2,320 total
includes taxes & fees
6 Feb - 7 Feb
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.
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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, Hickory Ski Center, 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.