Winchester, VA: All You Must Know Before You Go (2024) - Tripadvisor

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Plan Your Trip to Winchester: Best of Winchester Tourism

About Winchester
Sitting at the northernmost corner of Virginia in the Shenandoah Valley, Winchester offers visitors the chance to explore historical sites, museums, vineyards, farmers' markets, and tree-lined Old Town streets once wandered by the likes of George Washington and Stonewall Jackson. The fruitful fields of the surrounding Frederick County have earned the area the title "apple capital of the world," with the city hosting the Shenandoah Apple Blossom Festival annually for almost a century.

Essential Winchester

Winchester Is Great For

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Frequently Asked Questions about Winchester




If you're a more budget-conscious traveler, then you may want to consider traveling to Winchester between December and February, when hotel prices are generally the lowest. Peak hotel prices generally start between September and November.

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