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Best of Winchester Guide

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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.

All things to do » Things to do

Rocking S Ranch
Rocking S Ranch
Attraction type: Ranchs
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Museum of the Shenandoah Valley
Museum of the Shenandoah Valley
Owner description: The Museum of the Shenandoah Valley (MSV) is dedicated to preserving and enriching the cultural life and heritage of the Valley. This regional history complex includes a house... more Owner description: The Museum of the Shenandoah Valley (MSV) is dedicated to preserving and enriching the cultural life and heritage of the Valley. This regional history complex includes a house dating to the eighteenth century, six acres of spectacular gardens, and a 50,000-square-foot museum featuring changing exhibitions, a permanent display of miniature houses, and an expansive gallery exploring the history and decorative arts of the Shenandoah Valley. The MSV also includes a Museum Store and café (admission not required). The galleries are open year-round; the house and gardens April through October. The MSV sits on land originally claimed by Winchester founder James Wood in 1735. The property was passed through generations of Wood and Glass families until being acquired by Wood descendant and MSV benefactor Julian Wood Glass Jr. (1910–1992) between 1952 and 1955. Glass and his partner at the time, R. Lee Taylor (1924–2000), worked together to transform the site and its Glen Burnie House—built in 1794 by James Wood’s son Robert—into a country retreat where the couple entertained in high style.  less
Attraction type: Historic Sites; History Museums
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Stonewall Jackson's Headquarters
Stonewall Jackson's Headquarters
Attraction type: Historic Sites
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Handley Regional Library
Handley Regional Library
Attraction type: Libraries; Landmarks/ Points of Interest
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Old Court House Civil War Museum
Old Court House Civil War Museum
Attraction type: Museums
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All places to eat » Places to eat

Thai Win II
Thai Win II
Ranked #1 of 233 Restaurants in Winchester
Price: $10 - $20
Cuisines: Asian, Thai
Dining options: Delivery
Neighborhood Italian Kitchen
Neighborhood Italian Kitchen
Ranked #2 of 233 Restaurants in Winchester
Cuisines: Italian
Dining options: Delivery
Coach & Horses Tea Room
Coach & Horses Tea Room
Ranked #3 of 233 Restaurants in Winchester
Cuisines: British
Dining options: Reservations
Throx Market Station
Throx Market Station
Ranked #4 of 233 Restaurants in Winchester
Price: $5 - $13
Cuisines: American, Coffee Shop, Hamburgers, Sandwiches
Dining options: Breakfast/Brunch, Lunch
Violino Ristorante Italiano
Violino Ristorante Italiano
Ranked #5 of 233 Restaurants in Winchester
Price: $15 - $30
Cuisines: Italian
Good for: Romance, Outdoor seating, Special occasions, Entertaining clients
Dining options: Lunch, Dinner, Reservations

All accommodations » Where to stay - Budget

Nearby recommended accommodations:

Holiday Inn Express Winchester South
2.5 of 5
Holiday Inn Express Winchester South
$76 - $108
Ranked #1 of 2 Hotels in Stephens City
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Comfort Inn
2.0 of 5
Comfort Inn
$84 - $102
Ranked #2 of 2 Hotels in Stephens City
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Hampton Inn Martinsburg South - Inwood
2.5 of 5
Hampton Inn Martinsburg South - Inwood
$93 - $113
Ranked #1 of 1 Hotels in Inwood
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All accommodations » Where to stay - Midrange

Country Inn & Suites Winchester
2.5 of 5
Country Inn & Suites Winchester
$77 - $120
Ranked #1 of 27 Hotels in Winchester
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Nancy Shepherd House Inn - Bed & Breakfast
Nancy Shepherd House Inn - Bed & Breakfast
$99 - $129
Ranked #2 of 4 Winchester B&B and Inns
Holiday Inn Winchester Southeast-Historic Gateway
3.0 of 5
Holiday Inn Winchester Southeast-Historic Gateway
$90 - $134
Ranked #3 of 27 Hotels in Winchester
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Note: This information was accurate when it was published, but can change without notice. Please be sure to confirm all rates and details directly with the companies in question before planning your trip.