Photo by Julie Miller

Find Family Hotels in Chestertown, NY

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Pick from 6 Chestertown Family Hotels and compare 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, (83)
"Great room, very nice staff. Nice weekend getaway."
The price is SAR 571
SAR 634 total
includes taxes & fees
23 Nov - 24 Nov
Friends Lake Inn
Lily Pad South at Loon Lake near Gore Mountain
Sledding, skiing, snowboarding at Dynamite Hill
Lily Pad South at Loon Lake near Gore Mountain
9.8 out of 10, Exceptional, (42)
"Very clean and spacious. Our hosts were very quick to respond to any questions that we had. Use of boats, canoes, and kayaks, all included, and just a few minutes to the sandy town beach. We had a lovely stay"
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 2,204
SAR 2,432 total
includes taxes & fees
29 Nov - 30 Nov
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, 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.