Find Family Hotels in Old Town Winchester, VA

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Old Town Winchester Family Hotels

This weekend
Next weekend

Top Old Town Winchester Family Hotels

The George Washington Hotel, A Wyndham Grand Hotel

3.5 star property
9.4 out of 10, Exceptional, (1006)
"Our stay was wonderful. The rooms were clean, all staff was helpful, pool/hot tub was perfect with the cold weather and the entertainment at the bar was phenomenal. "
Amanda
The price is SAR 475
SAR 538 total
includes taxes & fees
28 Jul - 29 Jul
The George Washington Hotel, A Wyndham Grand Hotel
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.

Top Old Town Winchester Hotel Reviews

Frequently asked questions

What's Old Town Winchester like for family-friendly vacations?
The walkable destination of Old Town Winchester is a great choice if you've been thinking about a vacation with the kids. The local tours and cafes are just a few things that make this an attractive spot for a family vacation. Take to the air and fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the center of Old Town Winchester.
When's the best time to book a family-friendly vacation in Old Town Winchester?
The hottest months are usually July and August with an average temperature of 72°F,
  • Coldest months: January, February, December, and March
  • Driest months: November, January, February, and March
  • Rainiest months: May, September, June, and July
What's there to see and do with your family in Old Town Winchester?
While you and your family are staying in Old Town Winchester, you might want to visit some family-friendly attractions such as Bright Box Theater, Handley Regional Library, and Winchester Little Theater. Make sure you have lots of time for activities like Apple Blossom Mall and Dinosaur Land.