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

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$199 per night from 12 July to 13 July
AU$199
12 July - 13 July
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel: Business-friendly hotel with an indoor pool and 2 restaurants. Located in the city centre.
"Very charming historic hotel. Close to very nice restaurants and tourist District."

Reviewed on 4 July 2026

Opens in a new windowThe George Washington Hotel, A Wyndham Grand Hotel
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$130 per night from 19 July to 20 July
AU$130
19 July - 20 July
includes taxes & fees
TRU By Hilton Winchester: Pet-friendly hotel with free breakfast and free WiFi. Guests love the helpful staff!
"Good location but floor was sticky in room and no closets, just open hooks."

Reviewed on 4 July 2026

Opens in a new windowTRU By Hilton Winchester
Spark by Hilton Winchester

Spark by Hilton Winchester

3 out of 5
150 Wingate Dr Winchester VA
Fully refundableReserve now, pay when you stay
The price is AU$126 per night from 20 July to 21 July
AU$126
20 July - 21 July
includes taxes & fees
Spark by Hilton Winchester: Pet-friendly hotel with free breakfast and free parking. Guests love the helpful staff!
"This newly renovated, squeaky clean hotel is a favorite of ours as a stop off on our I-81 journeys. It is at an excellent location, quiet, clean, and the rooms are spacious. Hotel gym, breakfast, and pool are excellent additions to our stay here. They are also pet friendly and have a nice spot to ..."

Reviewed on 28 June 2026

Opens in a new windowSpark by Hilton 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.