Winchester Holiday Packages

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Our amazing packages combine your hotels and flights to make travelling a breeze.

With your extra funds, the possibilities are endless in Winchester.

How does an additional sound to you? That's how much you could save if you book right now. And don't forget — you've got the freedom to mix and match from more than 550 partner airlines and 665,000 properties.

Don't waste time trawling the internet when you really should be packing a bag. Wotif has some of the leading prices out there.

Winchester Accommodation

Choosing a place to spend your evenings can be a complex task if you don't know the area. With an impressive 21 accommodations in Winchester to choose from, Wotif's useful filter tool will be your new best friend.

Whether you're planning to spend lots of time in bed or you think you might be cruising around town for most of your holiday, The George Washington Hotel, A Wyndham Grand Hotel and Hilton Garden Inn Winchester are highly recommended options.

Car Hire in Winchester

If you're eager to rent a ride shortly after landing at Eastern West Virginia Regional Airport, make your way to Enterprise (901 N Queen St), a short drive away. They'll get you and your posse on the road in a jiffy. Just remember to bagsy the front seat.

Enterprise (2711 Valley Ave) is just 4 kilometres from the city centre, so you won't have to wait too long to pick up those keys.

Holidays to Winchester

An amazing holiday begins with knowing the facts about where you're headed towards. So make yourself a coffee, stop for a few minutes and brush up on some facts about Winchester.

Want to visualise where you'll be based? Winchester sits 100 kilometres west of the well-known city of Washington.

With so many terrific activities on offer in the area, it's not hard to see why 26 000 people call this part of Shenandoah Valley home.

Top Winchester hotels

La Quinta Inn & Suites by Wyndham Winchester

La Quinta Inn & Suites by Wyndham Winchester

3 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
La Quinta Inn & Suites by Wyndham Winchester: Pet-friendly hotel with free breakfast and free WiFi. Located in the suburbs.
"The staff was very friendly and the room was comfortable and clean."

Reviewed on 8 Jun. 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
Holiday Inn Winchester Se-Historic Gateway by IHG: Business-friendly hotel with free WiFi and free parking. Located in the historical district.
"It was at best average."

Reviewed on 9 Jun. 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
Travelodge by Wyndham Winchester

Travelodge by Wyndham Winchester

2.5 out of 5
160 Front Royal Pike, Winchester, VA
Fully refundableReserve now, pay when you stay
Travelodge by Wyndham Winchester: Pet-friendly motel with free WiFi and free parking. Guests love the helpful staff!
"The property was old but it was clean, quiet and well maintained. Thanks!"

Reviewed on 12 Jun. 2025

Travelodge by Wyndham Winchester
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.