Family Hotels & Resorts in Sterling

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Best Sterling Family Hotels

Beautiful view of the beach with palm trees

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Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

What's Sterling like for family-friendly holidays?
You may want to consider the relaxing destination of Sterling if you’ve been thinking about a trip for the whole family. The entertainment, festivals and golf are just a few things that make this an attractive holiday destination for families. Fly into Worcester, MA (ORH-Worcester Regional), which is located 12.9 mi (20.7 km) from the city centre.
What's the best family accommodation in Sterling?
Chocksett Inn and Restaurant is a hotel with a restaurant and free parking, and it’s a top choice on Expedia for families.
When's the best time to book a family-friendly holiday in Sterling?
The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Sterling are January, November, February and March, with each month seeing an average of 23 cm of snowfall.
What's there to see and do with your family in Sterling?
While you and your family are staying in Sterling, you may want to visit some family-friendly attractions such as Davis’ Farmland & Mega Maze, Wachusett Mountain Ski Area and Wachusett Mountain State Reservation. Make sure that you have lots of time for activities such as Great Wolf Lodge Waterpark and Solomon Pond Mall.