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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

Stonewall Jackson's Headquarters
Stonewall Jackson's Headquarters
Attraction type: Historic Sites
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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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Handley Regional Library
Handley Regional Library
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Shenandoah Valley Discovery Museum
Shenandoah Valley Discovery Museum
Owner description: Our mission at the Shenandoah Valley Discovery Museum is to ignite creativity, spark curiosity and inspire learning in visitors of all ages by providing a rich variety of... more Owner description: Our mission at the Shenandoah Valley Discovery Museum is to ignite creativity, spark curiosity and inspire learning in visitors of all ages by providing a rich variety of interactive, hands-on exhibits and programs that focus on the sciences and mathematics, the humanities, and the arts.All exhibits, activities and experiences provided by the Discovery Museum adhere to the following philosophical guidelines:Exhibits, activities and programs are interactive, participatory and informal, and give visitors opportunities to experiment, have fun playing, use their imaginations and share ideas.Visitors are engaged at their own level of expertise and experience.Activities and programs are multi-sensory, authentic, honest, and factual.The Museum works in a spirit of cooperation and partnership with educational, cultural, governmental and community organizations. less
Attraction type: Science Museums
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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 230 Restaurants in Winchester
Price: $10 - $20
Cuisines: Asian, Thai
Dining options: Delivery
Coach & Horses Tea Room
Coach & Horses Tea Room
Ranked #2 of 230 Restaurants in Winchester
Cuisines: British
Dining options: Reservations
Throx Market Station
Throx Market Station
Ranked #3 of 230 Restaurants in Winchester
Price: $5 - $13
Cuisines: American, Coffee Shop, Hamburgers, Sandwiches
Dining options: Breakfast/Brunch, Lunch
One Block West
One Block West
Ranked #4 of 230 Restaurants in Winchester
Price:
Cuisines: American, Eclectic, Wine Bar
Good for: Romance, Doing business, Local cuisine, Outdoor seating, Special occasions, Entertaining clients
Dining options: Breakfast/Brunch, Lunch, Dinner, Reservations, Late Night
Violino Ristorante Italiano
Violino Ristorante Italiano
Ranked #5 of 230 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
$95 - $110
Ranked #1 of 2 Hotels in Stephens City
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Comfort Inn
2.0 of 5
Comfort Inn
$88 - $105
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 - $111
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 - $119
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 - $111
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.