Deals on vacations and trips to Winchester
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Winchester flight + hotel vacation packages
DoubleTree Hotel Baltimore - BWI Airport
Sagamore Pendry Baltimore
Salamander Washington DC
The Graham Georgetown
Top Winchester hotels deals
La Quinta Inn & Suites by Wyndham Winchester
Microtel Inn & Suites by Wyndham Winchester
Travelodge by Wyndham Winchester
Comfort Inn & Suites
Red Roof Inn Winchester, VA
The George Washington Hotel, A Wyndham Grand Hotel
Popular places to visit
Museum of the Shenandoah Valley
You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.
Handley Regional Library
After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.
Shenandoah University
Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.
Winchester Vacations
Tourists regularly plan Winchester vacations to see the "Apple Capital" of the eastern seaboard. With vast orchards surrounding the city, this part of Virginia retains the robust apple industry of its founding days. When you're booking Winchester packages, look for deals around the spring and summer holidays, as they're the best time to experience local events and catch the peak of apple season.
Major Attractions in Winchester
Old Town Winchester is the tourist center of the city, home to dozens of historical attractions, plus over a hundred hotels, restaurants, and locally owned stores. It's also a great place to look for Winchester hotels, and its proximity to the Winchester Regional Airport makes it convenient to find Winchester rental cars.
Many tourist buffs book flights and Winchester all-inclusive vacations just to see the dozens of notable Civil War sites. You can even sign up for a guided tour of historic Civil War locations -- most reliably during the spring, summer, and fall, although tours exist year-round. Notable sites include the headquarters of Stonewall Jackson when he led campaigns in the area, and even the headquarters of General George Washington during the Revolutionary War.
Festivals and Events in Winchester
By far the biggest annual event in Winchester is the world-famous Shenandoah Apple Blossom Festival. Typically held at the start of May, this festival has grown to encompass more than 30 events, including barn dances, band competitions, multiple parades, a carnival, and a circus, plus it features a celebrity Grand Marshal.
Beyond the Apple Blossom Festival, Old Town Winchester hosts events throughout the year. With scavenger hunts in August and Civil War re-enactments from June through September, these activities take advantage of Old Town's deep historic heritage and its ample opportunities for delicious dining!
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Photos of local treasures
Frequently asked questions
Where to stay in Winchester: Best areas for travelers
- Blue Ridge: You won't need to choose between a nature escape and a city trip here. With popular attractions like Blue Ridge Center for Environmental Stewardship and Aldie Mill Historic Park, this Winchester neighborhood has the best of worlds. Discover these sights from the Goodstone Inn & Restaurant or the Salamander Resort And Spa. The Middleburg Historic District Charm is also a comfortable base.
- Stephens City: You've made an itinerary of all the top attractions in town. Now all you need is a cozy hotel to return to. For an enjoyable vacation, lock in a room at the Quality Inn Stephens City-Winchester South or the Holiday Inn Express Winchester South-Stephens City.