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Find kid-friendly hotels & resorts in Old Town Winchester, VA from $98

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Best Old Town Winchester Family Hotels

The George Washington Hotel, A Wyndham Grand Hotel
Great for families
3.5 out of 5
103 E Piccadilly St, Winchester, VA
Free CancellationReserve now, pay when you stay
The price is $98 per night from May 2 to May 3
4.6/5Exceptional! (982 reviews)
Families like: indoor pool, skiing nearby, extra beds/cribs, laundry
Travelers say...

"The renovation of the Hotel was excellent and much of the original hotel was still present."…"

Reviewed on Apr 10, 2021

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.

Family Friendly Hotels with Indoor Pools

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA
The price is $98 per night from May 2 to May 3
4.6/5Exceptional! (982 reviews)
The George Washington Hotel, A Wyndham Grand Hotel

Hotels with Connecting Rooms

The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

103 E Piccadilly St, Winchester, VA
The price is $98 per night from May 2 to May 3
4.6/5Exceptional! (982 reviews)
The George Washington Hotel, A Wyndham Grand Hotel

Where Should We Stay in Old Town Winchester?

If you've been thinking about a trip with your kids, the walkable destination of Old Town Winchester is a good choice. The local tours and cafés are just a few things that make this an attractive family vacation destination. Arrange a flight into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city center. After arriving in Old Town Winchester, you may want to choose a lodging option the whole family will enjoy.

Families on vacation have positive things to say about this accommodation:

The George Washington Hotel, A Wyndham Grand Hotel - Offers an indoor pool, 2 restaurants, and free WiFi. This hotel is rated 3.5 stars.

When Should We Visit Old Town Winchester?

You're likely hoping for good weather for your family trip. Use these tips to plan when to pack up the kids and head to Old Town Winchester.

  • Hottest months: July, June, August, and September, with an average temperature of 84°F
  • Coldest months: January, February, December, and March, with an average temperature of 25°F
  • Driest months: February, January, December, and October, with an average rainfall of 2.63 inches
  • Rainiest months: May, September, June, and July, with an average rainfall of 3.69 inches

What Should We See and Do in Old Town Winchester?

While you are visiting Old Town Winchester, you and the family might want to check out some interesting spots such as Bright Box Theater, Old Court House Civil War Museum, and Shenandoah Valley Discovery Museum. Make sure you have lots of time for activities like Winchester Little Theater and Museum of the Shenandoah Valley.

Old Town Winchester is also well-known for its:
  • Shopping
  • Restaurants
  • Historical sites
  • Cafés
  • Live music
  • Tours

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Frequently asked questions

What's Old Town Winchester like for family-friendly vacations?
The walkable destination of Old Town Winchester is a good choice if you’ve been considering a getaway with your kids. The local tours and cafés are just a few things that make this an attractive spot for a family vacation. Fly into Martinsburg, WV (MRB-Eastern West Virginia Regional), which is located 18 mi (28.9 km) from the city center.
What's the best place to stay for a family trip to Old Town Winchester?
The George Washington Hotel, A Wyndham Grand Hotel is a top 3.5-star hotel on Expedia for families, and features an indoor pool and 2 restaurants.
What's the weather like in Old Town Winchester?
The hottest months are usually July and June with an average temp of 71°F, while the coldest months are January and February with an average of 36°F. Average annual precipitation for Old Town Winchester is 38 inches.
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 Shenandoah Valley Discovery Museum, Bright Box Theater, and Old Court House Civil War Museum. Make sure you have lots of time for activities like Handley Regional Library and Apple Blossom Mall.