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.

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 2,247
SAR 2,478 total
includes taxes & fees
8 Oct - 9 Oct
The Fern Lodge
Pine Tree Motel & Cabins
Exterior
Pine Tree Motel & Cabins
2.0 star property
9.2 out of 10, Wonderful, (121)
"The host was very warm and welcoming. I felt accommodated and all my questions were answered. The cabin was just right for traveling solo. Was a little put off by the fact of having the fridge and microwave in the bathroom and noticed that the front door didn't seal on one side so the cold air came right through making the room a bit chilly. Over all I did enjoy the stay."
The price is SAR 694
SAR 770 total
includes taxes & fees
29 Sep - 30 Sep
Pine Tree Motel & Cabins
Friends Lake Inn
Property entrance
Friends Lake Inn
4.0 star property
8.8 out of 10, Excellent, (81)
"This hotel is beautiful, old style Adirondacks with cute rooms and great dining. While it is charming, the bed at least in the room I had was a springboard type of mattress you’d find at a koa camp. For the price to stay there I was shocked with it being one of the most uncomfortable sleeps I’ve gotten at any hotel and I travel a lot. Beds are an important piece to me. Aside from the super uncomfortable bed, the place was really nice. They didn’t skip on any Adirondack decor, the food for dinner...
The price is SAR 837
SAR 929 total
includes taxes & fees
29 Sep - 30 Sep
Friends Lake Inn
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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.
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, Revolution Rail Co., and Strand Theater. Make sure you have lots of time for activities like Blue Line Outdoor Center and Up Yonda Farm Environmental Education Center.