Find Family Hotels in Chestertown, NY from CA $94

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Family Hotels

This weekend
Next weekend

Our top choices for Chestertown family-friendly hotels

Lily Pad South at Loon Lake near Gore Mountain

Lily Pad South at Loon Lake near Gore Mountain
Chestertown
9.8 out of 10, Exceptional, (49 reviews)
"We had a great time at the Lily Pad. Spent a day at Lake Placid and another day at Lake George...plus took in some of the sights and enjoyed the nearby beach and kayaksThe place was very nice...we would stay there again"
United States
Ray V.
The price is CA $158
CA $373 total
includes taxes & fees
Mar 8 - Mar 9
Lily Pad South at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain
Chestertown
10.0 out of 10, Exceptional, (115 reviews)
"Cozy home in the Adirondacks. It had everything we needed for 19 relatives for a family reunion. "
United States
Kathy B.
The price is CA $341
CA $953 total
includes taxes & fees
Mar 8 - Mar 9
Eagles Nest at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (40 reviews)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
The price is CA $251
CA $662 total
includes taxes & fees
Mar 8 - Mar 9
The Lily Pad at Loon Lake near Gore Mountain

Family Friendly 3BR 3.5BA Lodge w/ Lake & Beach, Screened Patio, Grill, Sunroom

Family Friendly 3BR 3.5BA Lodge w/ Lake & Beach, Screened Patio, Grill, Sunroom
Chestertown
10.0 out of 10, Exceptional, (3 reviews)
"Rooms were very clean. Location was great, next to many hiking spots. However, far from many common stores. Was beautiful "
United States
MiaMaria C.
The price is CA $279
CA $757 total
includes taxes & fees
Mar 9 - Mar 10
Family Friendly 3BR 3.5BA Lodge w/ Lake & Beach, Screened Patio, Grill, Sunroom

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

Country Inn & Suites by Radisson, Lake George (Queensbury), NY
3.0 star property
Queensbury
9.0 out of 10, Wonderful, (1,364 reviews)
"Very friendly and helpful staff, clean rooms. Front desk staff very friendly and accommodating. Will certainly consider staying here again when we visit the area. "
United States
Daniel
The price is CA $120
CA $134 total
includes taxes & fees
Mar 8 - Mar 9
Country Inn & Suites by Radisson, Lake George (Queensbury), NY

The Queensbury Hotel

The Queensbury Hotel
3.0 star property
Glens Falls
9.4 out of 10, Exceptional, (1,535 reviews)
"great place "
United States
Scott
The price is CA $134
CA $149 total
includes taxes & fees
Mar 8 - Mar 9
The Queensbury Hotel

Silver Bay YMCA Inn and Conference Center

Silver Bay YMCA Inn and Conference Center
2.0 star property
Silver Bay
8.8 out of 10, Excellent, (139 reviews)
"Yes but wished they had tv’s"
United States
Gina
The price is CA $146
CA $163 total
includes taxes & fees
Apr 1 - Apr 2
Silver Bay YMCA Inn and Conference Center

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (22 reviews)
"Great updated cabin. "
United States
Diane
The price is CA $278
CA $343 total
includes taxes & fees
Mar 9 - Mar 10
Trout House Village Resort

La Quinta Inn & Suites by Wyndham Lake George

La Quinta Inn & Suites by Wyndham Lake George
3.0 star property
Lake George
8.8 out of 10, Excellent, (1,685 reviews)
"Great staff and fun place for the kids. "
United States
Robert
The price is CA $137
CA $152 total
includes taxes & fees
Mar 9 - Mar 10
La Quinta Inn & Suites by Wyndham Lake George

Red Roof Inn Queensbury

Red Roof Inn Queensbury
2.5 star property
Queensbury
7.0 out of 10, Good, (1,001 reviews)
"Floor was dirty, noticed as I was packing to leave a tampon wrapper on the floor. Marijuana smell throughout. NO soap at all, was dispensers for shampoo, conditioner and hand soap and all were empty. Would not stay here again even if it was only $50"
United States
Jennifer
The price is CA $97
CA $107 total
includes taxes & fees
Mar 9 - Mar 10
Red Roof Inn Queensbury
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.

Choose what matters most at family-friendly hotels in Chestertown

The Annual Vacation Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.

Top Chestertown Hotel Reviews

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.
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 The Sembrich. Make sure you have lots of time for activities like Seagle Music Colony and Up Yonda Farm Environmental Education Center.

Explore a world of travel with Expedia