Winchester Holidays from AU$2,214

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Your Winchester Holiday

Lock in a Winchester holiday package and focus on what matters — enjoying yourself. This means no more planning stresses, just more free time to experience the best of this captivating city, such as its rich history and small-town feel. Want to explore? Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall are a few of the best places to visit during your trip to Winchester. No matter your travel plans or the size of your budget, organising a tailored Winchester holiday is a cinch with Expedia.

The Latest Winchester Holiday Deals

Price found within the past 48 hours. Click for updated prices.
The Bethesdan Hotel, Tapestry Collection by Hilton

The Bethesdan Hotel, Tapestry Collection by Hilton

4 out of 5
Bethesda Downtown
Price was AU$2,429, price is now AU$2,214 per person
AU$2,214
per person
22 Sept - 26 Sept
found 17 hours ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
8.6/10 Excellent! (1,909 reviews)
Everything perfect

Reviewed on 18 July 2026

Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
Tysons
Price was AU$3,061, price is now AU$2,581 per person
AU$2,581
per person
22 Sept - 26 Sept
found 17 hours ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
8.8/10 Excellent! (1,001 reviews)

Holiday Inn National Airport/Crystal City by IHG

Holiday Inn National Airport/Crystal City by IHG

3.5 out of 5
Crystal City
Price was AU$2,415, price is now AU$2,236 per person
AU$2,236
per person
22 Sept - 26 Sept
found 17 hours ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
8.2/10 Very good! (1,956 reviews)

The Westin Tysons Corner

The Westin Tysons Corner

4 out of 5
Idylwood
Price was AU$2,567, price is now AU$2,390 per person
AU$2,390
per person
22 Sept - 26 Sept
found 17 hours ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
8.8/10 Excellent! (1,015 reviews)
Clean room, staff, breakfast, great service

Reviewed on 18 July 2026

citizenM Washington DC Georgetown

citizenM Washington DC Georgetown

4 out of 5
Northwest
Price was AU$2,649, price is now AU$2,472 per person
AU$2,472
per person
22 Sept - 26 Sept
found 17 hours ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
8.8/10 Excellent! (40 reviews)
I loved my stay very much I would definitely stay there next time I come to Washington DC

Reviewed on 17 July 2026

Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
27,300
Max Temp Winter
4ºC
Max Temp Summer
29ºC
Top Sights
Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theatre

Our pick of the best Winchester Hotel Deals

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
The price is AU$137 per night from 2 Aug to 3 Aug
AU$137
2 Aug - 3 Aug
includes taxes & fees
Holiday Inn Winchester Se-Historic Gateway by IHG
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$145 per night from 26 July to 27 July
AU$145
26 July - 27 July
includes taxes & fees
TRU By Hilton 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$198 per night from 6 Aug to 7 Aug
AU$198
6 Aug - 7 Aug
includes taxes & fees
The George Washington Hotel, A Wyndham Grand Hotel
See all 2,113 properties in Winchester
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Stay near popular Winchester attractions

Museum of the Shenandoah Valley

8.8/10 (129 reviews)
Discover the Shenandoah Valley's rich heritage at this cultural cornerstone. Wander through the historic Glen Burnie House and meticulously designed gardens for a refined afternoon of regional exploration.
See properties

Frequently asked questions

How much does a Winchester holiday package cost?
Offering excellent value package deals from AU$2,214 on Expedia, you'll be surprised at how little a holiday to Winchester costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winchester?
If you'd like to score a cheap Winchester holiday package, consider travelling in December, January and February. You're likely to find better prices on flights and accommodation during these months — perfect for travellers wishing to save money.
How many days is enough for Winchester?
Allow around 2 days for your Winchester holiday in order to enjoy everything that makes this place unique. Wander around key areas, including Old Town Winchester and College Park. Then check out major sights like Abram's Delight and Museum of the Shenandoah Valley. With a clever itinerary, you can keep busy with room for some rest time too. Want to go beyond Winchester? Consider fitting in an excursion or two.
Is it worth booking a holiday package to Winchester?
It's easy to see why a Winchester holiday is on the to-do list of many travellers. Top attractions like Shenandoah Valley Discovery Museum are just the start of what you can explore here.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your travel dates and destination under our "Packages" tab. Then add some filters, like "Popular locations" and "Amenities," to fine-tune the results to your exact needs. You can also sort by "Package discount" and discover offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Remember that deals are only available for a limited time, so book early and get your Winchester escape underway.
Is it cheaper to book a Winchester holiday as a package?
You can enjoy significant savings on your next Winchester retreat by booking a tailored holiday package. Check the "Package" heading, then enter your travel dates and destination to browse some great hotel and flight prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may land a better deal.
When to book a holiday package to Winchester?
Enjoy incredible discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winchester trip.
How to plan a trip to Winchester?

  1. Choose when to travel: Check your schedule and get your bags packed. Your favourite time of year and the activities available will also help you decide when to holiday in Winchester.
  2. Set a budget: Consider expenses such as flights, food and transportation when calculating how much to set aside for your trip to Winchester. Then, pick a property that fits your budget, whether that's a wallet-friendly option or a more luxurious retreat.
  3. Decide how long to go for: Now that you know more about Winchester, you can figure out the perfect length of your break. Put together a rough plan and give yourself enough time for all the things you want to do.
  4. Combine your hotel and flights: Epic destination, check. Length of stay, check. Now all that's left is to find a Winchester holiday package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.