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Find Family Hotels in Chestertown, NY

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Check availability on Chestertown Family Hotels

Top Chestertown Family Hotels

Pine Tree Motel & Cabins
Exterior

Pine Tree Motel & Cabins

2.0 star property
9.2 out of 10, Wonderful, (129)
"Excellent location and staff was very friendly."
The price is ₩242,909
₩269,629 total
includes taxes & fees
Jul 20 - Jul 21
Pine Tree Motel & Cabins
Friends Lake Inn
Premier Room | 1 bedroom, premium bedding, individually decorated

Friends Lake Inn

4.0 star property
8.8 out of 10, Excellent, (90)
"Quiet lodging and friendly staff"
The price is ₩325,942
₩361,781 total
includes taxes & fees
Jul 21 - Jul 22
Friends Lake Inn
The Fern Lodge
Lake view

The Fern Lodge

3.5 star property
9.8 out of 10, Exceptional, (46)
"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 ₩748,228
₩830,525 total
includes taxes & fees
Aug 3 - Aug 4
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.

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, 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.