Winchester, Virginia Bed and Breakfasts
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Winchester Virginia, the oldest English settlement west of the Blue Ridge Mountains, and Frederick County invite you to Get a Better View of History. Come explore her rich history. Young George Washington surveyed Winchester which was part of the original Lord Fairfax grant and then returned to Winchester as a Colonel in the militia, established his office which stands at the corner of Cork and Braddock Streets and is open as a museum, built Fort Loudoun and developed his military skills in the French and Indian War. George Washington was elected to his first political office representing Frederick County in the Virginia House of Burgesses. Winchester's geographic location made it a significant factor in the Civil War. Winchester was the site of several battles—Kernstown, Winchester, Cedar Creek—and changed hands over 70 times during the war. Stonewall Jackson's headquarters is now a popular museum. The Old Court House Civil War Museum is an amazing collection of weapons, medical tools, and everyday items. An outstanding feature of the museum is the preserved graffiti which was written on the interior walls by soldiers who were being held as prisoners.
The Museum of the Shenandoah Valley, located on the grounds of Glen Burnie, home of Winchester's founder, James Wood. Along with the historic sites in Old Town you may choose to experience a close-up guided walking GHOST TOUR—Historic Haunts—to learn the stories of the Winchester ghosts. Springtime means that the annual Shenandoah Apple Blossom Festival is just around the corner. Every Friday night during the summer the Bluemont Concert Series presents live performances on the lawn of the old Frederick County Courthouse. Enjoy a driving tour following the Apple Trail signs and listening to an entertaining and informative tape or CD available at the Winchester-Frederick County Convention and Visitor Center. An easy self-guided walking tour leads you by, and in, the remarkable architecture of historic downtown Winchester.
And So Many More Things To See and Do!!!
Come, we'll look forward to welcoming you to Winchester-Frederick County where you will
Get a Better View of History!
![]() Old Waterstreet InnDistance from city center: less than 1 milePhone: 540-665-6777 Toll Free: 866-665-6770 Located in the historic Old Town, just 2 blocks from the charming pedestrian street, where you'll find interesting shops, restaurants, galleries, and nightlife. It's the perfect place for a romantic getaway, a relaxing break, or a base for exploring the Valley. Winchester, Virginia View Listing Website Availability |
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![]() Long Hill Bed & BreakfastDistance from city center: 2 mile(s)Phone: 540-450-0341 Toll Free: 866-450-0341 A custom built 10,000 sq.ft. house on 20 acres. Savor an award winning family style gourmet breakfast. View birds & wildlife. Great getaway, stopover, or vacation anchor. Shoot pool; work puzzles; Outdoor pool in season; Large private baths. Good food, good rest; feel like family when you leave. Winchester, Virginia View Listing Website |
Other Area Inns
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![]() L'Auberge ProvencaleDistance from city center: 10 mile(s)Phone: 540-837-1375 Toll Free: 800-638-1702 Discover the South of France in rural Virginia and take advantage of our many travel specials. Just one hour from the D.C. beltway and two hours from Baltimore, the Inn is located in the heart of Virginia hunt country. White Post (Winchester), Virginia View Listing Website Availability |
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![]() Smithfield Farm Bed & BreakfastDistance from city center: 12 mile(s)Phone: 540-955-4389 Toll Free: 877-955-4389 Our accommodations include 4 spacious guest rooms with private baths and a separate guest cottage with private bath and whirlpool tub. We offer a full, candlelit breakfast. You can also enjoy the animals on our 400 acre working farm and perhaps take home some of our meat, eggs, or pasta. Berryville (Winchester), Virginia View Listing Website Availability |
![]() Killahevlin B&B InnDistance from city center: 20 mile(s)Phone: 540-636-7335 Toll Free: 800-847-6132 Historic Edwardian Mansion on Civil War encampment hilltop site. Romantic setting for honeymoons/anniversaries. Spectacular views. Virginia Landmarks & National Register. Whirlpools, fireplaces, Irish Pub. Gourmet breakfast. Near Skyline Drive. Front Royal (Winchester), Virginia View Listing Website Availability |
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![]() Pembroke Springs RetreatDistance from city center: 29 mile(s)Phone: 540-877-2600 Toll Free: 888-348-1688 The flavor of Japan below Great North Mountain in the Shenandoah Valley. 175 acres of field, forest & trail with a stream, pond, and big springs. Star Tannery (Winchester), Virginia View Listing Website |
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Inn at Vaucluse SpringDistance from city center: 50 mile(s)Phone: 540-869-0200 Toll Free: 800-869-0525 The Inn at Vaucluse Spring is a fifteen room bed and breakfast inn spread throughout a small village of six guest houses surrounding a large limestone spring in Virginia's fabled Shenandoah Valley. Stephens City (Winchester), Virginia View Listing Website Availability |
![]() Lost Dog Bed & BreakfastDistance from city center: 50 mile(s)Phone: 540-955-1181 This casual, fun, romantic getaway B&B invites you to return to the gracious hospitality of yesteryear without leaving today's conveniences and comforts! Guest rooms offer private baths, cable TV, & Wi-Fi for your laptop. Guests enjoy walking to our fine restaurants only a few blocks away. Berryville (Winchester), Virginia View Listing Website Availability |








