Find kid-friendly hotels & resorts in Old Town Winchester, Winchester from $125

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Pick from 1 Old Town Winchester Family Hotels and compare room rates, reviews, and availability. Most hotels are fully refundable.

"Wonderful location and very comfortable beds"

$142 total

includes taxes & fees

Jun 16 - Jun 17

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Old Town Winchester Family Hotels information

Family Hotels in Old Town Winchester	1
Highest price	$125
Cheapest price	$125
Number of guest reviews	1,003
Total number of hotels in Old Town Winchester	312

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.

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.

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 Apple Blossom Mall. Make sure you have lots of time for activities like Winchester Little Theater and Appleland Sports Center.