Winchester Vacation Packages

If you're eager to package your hotel and flight bookings to save time and money, you've come to the right place! Kick back, relax and let the knowledgeable team at Orbitz help you dream up a truly amazing Winchester trip. How do savings of sound? Simply choose your preferred hotels, rental cars, airfares and experiences and you'll have a little extra spare change clattering around in your pockets! Additionally, our ever-expanding database has no less than 500,000 international hotel options and 500 airlines. Don't worry if you have trouble choosing — we can make it simple! There are endless room types, flight options and fabulous experiences to satisfy your wandering spirit. Which ones will you go for?

Where is Winchester?

The excitement's rising within. You're just about to book your ticket. But hang on a sec — you don't have the foggiest where Winchester is! Allow us to point you in the right direction. This destination is approximately 120 miles north of the capital of Virginia, Richmond. Winchester is also 17 miles northeast of Strasburg. The population of this area of Shenandoah Valley is approximately 26,000.

Places to Visit in Winchester

Sometimes the best way to get a sense of a historic place of learning is by roaming the grounds and soaking up the atmosphere. Spend a few hours at Shenandoah University reflecting on those who once graced its hallways and those who do today. Want some more options? Spend the day shopping at Apple Blossom Mall where you will be able to buy the perfect souvenirs to take back home. But there's more! Does it leave you with an impression? What was the artist attempting to achieve? Ask yourself these questions as you stroll the corridors of Museum of the Shenandoah Valley, a renowned art institution.

Car Rentals in Winchester

Fun and adventure are just around the corner with car rentals in Winchester. Ready to discover the region from the convenience of your own ride? If you're touching down at Eastern West Virginia Regional Airport and want to get a hold of a car fast, head to Enterprise. You'll find it at 901 N Queen St, 18 miles from the terminal. If you have plans to stay in the city, head on over to Enterprise at 2711 Valley Ave. It is located just 3 miles from the heart of town.

Places to Visit in Winchester

Sometimes the best way to get a sense of a historic place of learning is by roaming the grounds and soaking up the atmosphere. Spend a few hours at Shenandoah University reflecting on those who once graced its hallways and those who do today. Want some more options? Spend the day shopping at Apple Blossom Mall where you will be able to buy the perfect souvenirs to take back home. But there's more! Does it leave you with an impression? What was the artist attempting to achieve? Ask yourself these questions as you stroll the corridors of Museum of the Shenandoah Valley, a renowned art institution.

Nearest Airports to Winchester

Is there anything better than jumping on a plane, binging on movies and knowing that the beginning of your adventure is just hours away? Once you hit the tarmac at Washington Dulles International Airport (IAD), the closest airport to Winchester, you'll be just 40 miles from the center of town.

Popular Places to Visit Near Winchester

If you've seen the very best of Winchester already, don't panic. You've actually got renowned tourist attractions close at hand! Arlington National Cemetery lures people from all continents of the globe. Falls Church, about 55 miles from Winchester, is a handy base when stopping by this world-famous attraction.

No Cancellation Fees

Plans can change in an instant, which is why we won't ask for a fee if you need to cancel or revise your booking.^ However, it might be a good idea to see if your hotel and airline share the same policy.