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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!

Book your vacation on Travelocity today, and enjoy the Travelocity Price Guarantee. If you find a better price, we'll refund the difference!

Top Winchester Hotels Deals

$89
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5.0 118 Mercedes Court, Winchester, VA
4.6/5
(7 Reviews)
This hotel features an indoor pool and a health club. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A safe deposit box is also provided.
$67
Quality Inn

Quality Inn

2.5 out of 5.0 1601 Martinsburg Pike, Winchester, VA
4.5/5
(13 Reviews)
A restaurant and a fitness center are featured at this hotel. Traveling on business? Take advantage of the free WiFi in public areas and free Internet in public areas. Enjoy the seasonal outdoor pool and free perks like buffet breakfast and free self parking.
$93
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5.0 103 E Piccadilly St, Winchester, VA
4.1/5
(14 Reviews)
A full-service spa, 2 restaurants, and an indoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the 5 conference rooms, as well as the business center and free WiFi in public areas. You'll appreciate the 24-hour fitness center, bar/lounge, and laundry facilities.

Things to do in Winchester

See all 198 things to do in Washington

Top Flight Deals to Winchester

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

^Savings based on all package bookings made with Flight + Hotel on Travelocity.com from January 1, 2019 to December 31, 2019, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages.

*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.