Winchester Holiday Packages

Save when you book Winchester package deals

Choose two or more items and save on your trip:

Book your Winchester holiday

Save a little cash with Wotif.

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
The price is AU$154 per night from 16 Feb to 17 Feb
AU$154
16 Feb - 17 Feb
includes taxes & fees
La Quinta Inn & Suites by Wyndham Winchester: Pet-friendly hotel with free breakfast and free WiFi. Located in a shopping district.
The room was very large and spotless. Clean and filled with plenty towels!

Reviewed on 10 Feb 2026

Opens in a new windowLa Quinta Inn & Suites by Wyndham Winchester
The George Washington Hotel, A Wyndham Grand Hotel

The George Washington Hotel, A Wyndham Grand Hotel

3.5 out of 5
103 E Piccadilly St Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$196 per night from 22 Feb to 23 Feb
AU$196
22 Feb - 23 Feb
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel: Business-friendly hotel with free WiFi and an indoor pool. Located in the business district.
Clean nice room Great location for restaurants

Reviewed on 28 Jan 2026

Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
Microtel Inn & Suites by Wyndham Winchester

Microtel Inn & Suites by Wyndham Winchester

2.5 out of 5
150 Faraday Plaza Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$132 per night from 22 Feb to 23 Feb
AU$132
22 Feb - 23 Feb
includes taxes & fees
Microtel Inn & Suites by Wyndham Winchester: Pet-friendly hotel with free breakfast and free WiFi. Guests love the helpful staff!
The only thing that disappointed me is that the breakfast potatoes and omelets were quite spice. I was unable to eat them. However, the room was excellent.

Reviewed on 10 Feb 2026

Opens in a new windowMicrotel Inn & Suites by Wyndham Winchester
Don't see what you're looking for?
See all available properties in Winchester
View all properties
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.