Old Town Winchester Holidays from AU$1,875

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$703 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Old Town Winchester Holiday

Book a customised holiday package to Old Town Winchester and experience the wonders of this neighbourhood from sunup to sundown. From its cafes and history to its distinct personality and vibe, there are loads of good reasons to visit Old Town Winchester. Hoping to sightsee during your trip to Old Town Winchester? Don't miss nearby attractions like Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Stop daydreaming and start doing. When it's time to book your ideal holiday to Old Town Winchester, Expedia will help get you there.

Top Holiday Package Deals in Old Town Winchester

Price found within the past 48 hours. Click for updated prices.
Best Western Battlefield Inn

Best Western Battlefield Inn

2.5 out of 5
Price was AU$1,969, price is now AU$1,875 per person
AU$1,875
per person
20 Apr - 24 Apr
found 1 day ago
Return flight included
Sydney (SYD) to Washington (IAD)
7.2/10 Good! (1,001 reviews)
Nice and clean rooms and prompt front desk check in and check out 👍

Reviewed on 8 Feb 2026

Courtyard by Marriott Tysons McLean

Courtyard by Marriott Tysons McLean

3 out of 5
Price was AU$2,767, price is now AU$2,561 per person
AU$2,561
per person
20 Apr - 24 Apr
found 1 day ago
Return flight included
Sydney (SYD) to Washington (DCA)
8.6/10 Excellent! (1,000 reviews)
We had a great time at this hotel. Metro just a block away, 2 minutes drive to Tysons Corner shopping mall. The bar on the 2nd floor was great. Flemings steak house restaurant on the 1st floor was also great. Room was clean and with good space. Now, the walls must be made out of cardboard, We stayed 3 nights Fri-Sun and every single night we heard the heavy loud snoring from the guy next to our room, it was really bad to the point we had to sleep blasting white noise from our phones and we never sleep with white noise

Reviewed on 25 Jan 2026

La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

La Quinta Inn & Suites by Wyndham Manassas Va-Dulles Airport

3 out of 5
Price was AU$2,109, price is now AU$1,969 per person
AU$1,969
per person
20 Apr - 24 Apr
found 1 day ago
Return flight included
Sydney (SYD) to Washington (IAD)
8.6/10 Excellent! (940 reviews)
Friendly staff, nice breakfast (a lot choices), comfort bed and an updated bathroom.

Reviewed on 28 Jan 2026

Hyatt Regency Dulles

Hyatt Regency Dulles

4 out of 5
Price was AU$2,340, price is now AU$2,219 per person
AU$2,219
per person
20 Apr - 24 Apr
found 1 day ago
Return flight included
Sydney (SYD) to Washington (IAD)
8.8/10 Excellent! (1,496 reviews)
Nice amenities. Enjoyed

Reviewed on 14 Feb 2026

Aloft Dulles Airport North

Aloft Dulles Airport North

3 out of 5
Price was AU$2,160, price is now AU$2,071 per person
AU$2,071
per person
21 Apr - 24 Apr
found 1 day ago
Return flight included
Sydney (SYD) to Washington (IAD)
8.2/10 Very Good! (1,002 reviews)
Room was very clean. Reception was extremely helpful. One improvement note: let occupants know room service needs to be requested. I was expecting to return to a freshened room.

Reviewed on 8 Feb 2026

Our pick of the best Old Town Winchester Hotel Deals

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
9.2/10 Wonderful! (1,001 reviews)
Clean nice room Great location for restaurants

Reviewed on 28 Jan 2026

The George Washington Hotel, A Wyndham Grand Hotel
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
9.2/10 Wonderful! (2,264 reviews)
Staff was very courteous and friendly throught our entire stay! Everything was updated and very clean. Kids LOVED the pool and breakfast.

Reviewed on 10 Feb 2026

La Quinta Inn & Suites by Wyndham Winchester
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
The price is AU$108 per night from 16 Feb to 17 Feb
AU$108
16 Feb - 17 Feb
includes taxes & fees
8.4/10 Very Good! (1,082 reviews)
Room was good for the price, staff was friendly and helpful

Reviewed on 4 Feb 2026

Travelodge by Wyndham Winchester
See all 370 properties in Old Town 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

Frequently asked questions

How much does an Old Town Winchester holiday package cost?
Our Old Town Winchester holiday packages, which begin from just AU$1,875, are the best way to save. All you have to do is choose your preferred hotels, flights and rental car to create your perfect getaway.
How do I get a cheap travel package to Old Town Winchester?
Our Old Town Winchester holiday packages offer plenty of savings for the savvy wanderer. For the best deal, simply bundle your hotel, flights and extras (including activities) into a handy package. But low prices are only the start of your next epic adventure. Book with Expedia and you'll have more than 550 air carriers and 1 000 000 hotels around the world to pick from. Whatever your budget or style, there's a package that's perfect for you.
Where should I stay in Old Town Winchester?
A holiday in Old Town Winchester wouldn't be complete without checking out Shenandoah University, Winchester Medical Centre and Museum of the Shenandoah Valley. Spend your evenings near these tourist attractions and make sightseeing a breeze.
What are the top hotels in Old Town Winchester?
Whether you plan to stay for a night or a week in Old Town Winchester, you'll get a wonderful night's rest at The George Washington Hotel, A Wyndham Grand Hotel. This option is a favourite with lots of travellers.
How far in advance should I book my Old Town Winchester holiday?
You'll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester holiday nice and early. Airlines typically advertise tickets anywhere up to 12 months in advance, so start your planning as soon as possible. Having said that, Expedia is constantly working to give you the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Old Town Winchester travel package include?
Flights, hotels and car rentals — we connect you to all the best deals. All you'll have to do is decide on your favourite combination. Once you've made your booking, you can add on the exciting stuff like activities and tours. Our travel packages make it simple to craft an amazing Old Town Winchester getaway.
What should I know before booking an Old Town Winchester travel package?
We already have low prices. However, you'll enjoy even more bargains when you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and a terrific range of choice.
Can I choose my airline with an Old Town Winchester Expedia holiday package?
With a holiday package, you're in charge. Whether you're looking to fly to Old Town Winchester in economy or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines around the world.
If I'm not able to travel, can I cancel my Old Town Winchester holiday package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester holiday package in the last 24 hours? You may be able to make changes or cancellations for free. For older bookings, you may incur a fee from your hotel, airline or car rental company. For further information, browse our Customer Service Portal. We're here to help you every step of the way.

Discover the most popular places to visit in Old Town Winchester

George Washington's Office

You can find out about the history of Winchester with a visit to George Washington's Office. While in this walkable area, you can savour the top-notch restaurants.

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