Beginning of main content

862 Travelers rated Winchester highly for Historical Buildings and Scenery

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!
Book a package and join the 188 others who’ve received 100% off their flights this year!

Earn Orbucks instantly on every package with Orbitz Rewards!

Save more by booking your flight + hotel together!

Earn up to 10% back with the Orbitz Rewards Visa Card.

Top Rated Hotels for your Winchester Vacation

Estimated price for 1 night/2 adults

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
Free Cancellation
$93
4.4/5 (40 reviews)

Breakfast was great, beautiful hotel, pullout couch and sheets not very clean or comfy.

Reviewed on Jun 28, 2019
Situated in Winchester, this spa hotel is within a 10-minute walk of Handley Regional Library and Shenandoah Valley Discovery Museum. Winchester Little Theater ...
Holiday Inn & Suites Front Royal Blue Ridge Shadows
Holiday Inn & Suites Front Royal Blue Ridge Shadows
3.0 out of 5.0 111 Hospitality Drive, Front Royal, VA
Free Cancellation
$95
4.3/5 (25 reviews)

Tolit is not clear. I found a lot hairs on the hair dry, and they are everywhere in the bath room! Felt not good!

Reviewed on Aug 7, 2018
Situated in Front Royal, this golf hotel is 0.6 mi (1 km) from Blue Ridge Shadows Golf Club and 3.1 mi (4.9 km) from Jackson's Chase Golf Course. Bing Crosby ...
Country Inn & Suites by Radisson, Winchester, VA
Country Inn & Suites by Radisson, Winchester, VA
3.0 out of 5.0 141 Kernstown Commons Blvd, Winchester, VA
Free Cancellation
$81
4.3/5 (64 reviews)

Room was spacious and clean. Front desk staff were very accommodating, we needed a rollaway bed

Reviewed on Jul 6, 2019
Situated in Winchester, this hotel is 2.2 mi (3.5 km) from The Kernstown Battlefield and within 6 mi (10 km) of Shenandoah University and Rock Harbor Golf Course. ...
Motel 6 Winchester, VA
Motel 6 Winchester, VA
2.0 out of 5.0 2951 Valley Avenue, Winchester, VA
Free Cancellation
$61
4.2/5 (24 reviews)

Location was great, room clean, price was right, staff was fine

Reviewed on Jun 27, 2019
Located in the heart of Winchester, this motel is 0.8 mi (1.2 km) from The Kernstown Battlefield and within 3 mi (5 km) of Apple Blossom Mall and Abram's Delight. ...
Holiday Inn Winchester Se-Historic Gateway
Holiday Inn Winchester Se-Historic Gateway
3.0 out of 5.0 333 Front Royal Pike, Winchester, VA
Free Cancellation
$83
4.1/5 (34 reviews)

I forgot a pair of earrings on the night stand & when I went back they were gone. The staff said they did not find any earrings.

Reviewed on Jun 17, 2019
Situated near the airport, this hotel is within 3 mi (5 km) of Shenandoah University, Winchester-Frederick County Convention & Visitors Bureau, and Apple Blossom ...

Winchester Vacation Package Deals

Get cracking on your upcoming Winchester adventure! Let the team here at Orbitz bundle up irrestistible flight and hotel deals.

Choose your preferred hotels, airfares, experiences and rental cars for savings of up to $857*! Packaging your bookings is one of the best ways to save money.

Hold on, there's more to come! With 500,000 worldwide hotels on our system and 500 airlines, you'll have heaps of flexibility to tailor your trip to suit your needs.

Our packages will help you come up with the getaway you've been daydreaming about. With limitless options to combine your flights, hotels and more, all that's left to do is pack your bags and grab your passport!

Join Orbitz Rewards

Like the sound of really, really fast rewards? All you have to do is start booking with us and you'll gain Orbucks! It's an easy program we've created to reward you, lightning fast!

For perks and added extras at Orbitz Rewards VIP Hotels, just become a gold or platinum member. How? Stay four nights for gold status and 12 nights for platinum status. Also, don't forget — you can make use of your Orbitz Rewards points the next time you book.

Winchester Travel Guide

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

Although this institution is known for its reputation as a prestigious center for knowledge and learning, Shenandoah University also boasts some detailed design features. Like some more options? Spend an afternoon shopping at Apple Blossom Mall and pick up the perfect souvenirs to take back home. But wait, there's more! If you're a fine art enthusiast, your vacation can't end without a stop at Museum of the Shenandoah Valley.

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.

Where to stay in Winchester – Hotel Accommodation

Eager to start your vacation? Organize your room now! Orbitz has 21 hotels in Winchester.

Unsure where to book? Let us make it a little easier! Our favorite options are The George Washington Hotel, A Wyndham Grand Hotel and Hampton Inn - Winchester N/Convention Center.

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.

^Savings based on all package bookings with Flight + Hotel made on Orbitz.com from January 1, 2018 to December 31, 2018 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.