What's Chestertown like for family-friendly holidays?

You may want to consider the remote destination of Chestertown if you've been thinking about a trip for the whole family. The boating, horse riding and canoeing are just some of the things that make this the perfect spot for family trips. Take to the air and fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), which is located 23.6 mi (38 km) from the city centre.

What's the best place to stay for a family holiday 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 choice for your child-friendly holiday.

How many family-friendly hotels should I expect to find in Chestertown?

Expedia has 18 hotels in Chestertown that are great for families.

What's the seasonal weather like in Chestertown?

The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chestertown are February, January, March and December, with each month seeing an average of 23 cm of snowfall.

What's there to see and do with your family in Chestertown?

While you are visiting Chestertown, you and the family may want to explore some interesting spots such as Gore Mountain Ski Resort, Revolution Rail Co. and The Sembrich. Make sure that you have lots of time for activities such as Sagamore Glades and Pack Demonstration Forest.

Photo by Julie Miller

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Top Chestertown Family-Friendly Hotels

The Fern Lodge

46 Fiddlehead Bay Rd., Chestertown, NY, 12817

4.9/5 Exceptional! (26 reviews)

Families like: Games room, skiing nearby, free breakfast for the whole family, laundry

Travellers say...

"I would highly recommend The Fern Lodge. The is amazing. My husband describes it as a peaceful place. And it’s extremely clean. Sharon is great! She gave us a tour. We will definitely be back!!"

Reviewed on 14 Aug 2020

Pine Tree Motel & Cabins

5537 State Route 8, Chestertown, NY, 12817

4.5/5 Wonderful! (91 reviews)

Families like: Playground, near the beach, extra beds/cots, games and toys

Cozy and Cute lodgings.

"Cozy, cute and clean lodgings. Owner was super friendly and beds were comfy. My daughter and I stayed here for a quick overnight. It’s conveniently located and set back off of Rt 8 in Chestertown. We had a quiet and restful stay."

Reviewed on 12 Oct 2021

Friends Lake Inn

963 Friends Lake Rd, Chestertown, NY, 12817

4.4/5 Wonderful! (59 reviews)

"We enjoyed everything about the property, especially the sauna. Staff is amazing especially Nicole, very vibrant and lively. Will definitely be back again."

Reviewed on 10 Apr 2022

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Chestertown Hotel Reviews
expedia verified reviews

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
5/5 Excellent
"My go to stay when in the area. "
A verified traveller stayed at Country Inn & Suites by Radisson, Lake George (Queensbury), NY
Posted 2 days ago
Country Inn & Suites by Radisson, Lake George (Queensbury), NY
The Queensbury Hotel
5/5 Excellent
"Staff is very welcoming. Veey clean place."
A verified traveller stayed at The Queensbury Hotel
Posted 2 days ago
The Queensbury Hotel
Six Flags Lodge & Indoor Waterpark
5/5 Excellent
"Everyone was nice and accommodating. What a wonderful experience. We will be back!!"
A verified traveller stayed at Six Flags Lodge & Indoor Waterpark
Posted 5 days ago
Six Flags Lodge & Indoor Waterpark
The Georgian Lakeside Resort
5/5 Excellent
"Nice Property good for family. "
A verified traveller stayed at The Georgian Lakeside Resort
Posted 5 days ago
The Georgian Lakeside Resort
Lakefront Terrace Resort
5/5 Excellent
"Great hotel, clean and well kept"
A verified traveller stayed at Lakefront Terrace Resort
Posted 5 days ago
Lakefront Terrace Resort
Americas Best Value Inn & Suites Lake George
5/5 Excellent
"We had a great stay at the hotel. We will definitely return."
A verified traveller stayed at Americas Best Value Inn & Suites Lake George
Posted 6 days ago
Americas Best Value Inn & Suites Lake George
Fort William Henry Hotel and Conference Center
5/5 Excellent
"Just loved to view "
A verified traveller stayed at Fort William Henry Hotel and Conference Center
Posted 7 days ago
Fort William Henry Hotel and Conference Center
Hampton Inn & Suites Lake George
5/5 Excellent
"Great hotel nice location the pool was little cold other than that I had a great time"
A verified traveller stayed at Hampton Inn & Suites Lake George
Posted 7 days ago
Hampton Inn & Suites Lake George
Howard Johnson by Wyndham Lake George
5/5 Excellent
"Very nice"
A verified traveller stayed at Howard Johnson by Wyndham Lake George
Posted 8 days ago
Howard Johnson by Wyndham Lake George