Old Town Winchester Holidays from AU$9,774

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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.
Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was AU$10,851, price is now AU$9,774 per person
AU$9,774
per person
20 June - 27 June
found 1 day ago
Return flight included
Melbourne (MEL) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Unexpected upgrade at check in. Was much appreciated!

Reviewed on 16 May 2026

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

5 out of 5
Northwest
Price was AU$13,464, price is now AU$11,539 per person
AU$11,539
per person
20 June - 27 June
found 1 day ago
Return flight included
Melbourne (MEL) to Baltimore (BWI)
9.4/10 Exceptional! (1,004 reviews)
If you're looking at this hotel, go ahead and book it! Not only is it luxurious and friendly, but you'll find at least 5 taxis by it at any time (a definite plus when certain Metro lines are being repaired). Added bonus: the signature house fragrance is unspeakably delicious. You will love your stay here!

Reviewed on 29 Apr 2026

Hotel Washington

Hotel Washington

5 out of 5
Downtown Washington D.C.
Price was AU$11,690, price is now AU$10,647 per person
AU$10,647
per person
20 June - 27 June
found 1 day ago
Return flight included
Melbourne (MEL) to Baltimore (BWI)
9/10 Wonderful! (2,407 reviews)
Great location, some restaurants nearby.

Reviewed on 10 May 2026

Washington Plaza Hotel

Washington Plaza Hotel

4 out of 5
Downtown Washington D.C.
Price was AU$12,090, price is now AU$11,059 per person
AU$11,059
per person
20 June - 27 June
found 1 day ago
Return flight included
Melbourne (MEL) to Baltimore (BWI)
8.8/10 Excellent! (5,132 reviews)
A great place to stay in downtown DC, easy to find and they have their own underground parking. This is an older property, but it’s in great shape. You can tell they keep on top of maintenance items and don’t let things get scruffy looking. I’ll book here again the next time I need to stay overnight in DC.

Reviewed on 15 May 2026

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was AU$11,481, price is now AU$10,525 per person
AU$10,525
per person
20 June - 27 June
found 1 day ago
Return flight included
Melbourne (MEL) to Baltimore (BWI)
9.4/10 Exceptional! (1,451 reviews)
We were welcomed with a glass of champagne or rose. Our room was comfortable and delightfully decorated, including thoughtful and useful items like an umbrella and tote bag. We ordered a quick dinner in Cafe Riggs. The portions were generous and the food was delicious. Staff was attentive and very friendly.

Reviewed on 10 May 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$207 per night from 9 June to 10 June
AU$207
9 June - 10 June
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
The staff was helpful and kind. The architecture was incredible.

Reviewed on 12 May 2026

The George Washington Hotel, A Wyndham Grand Hotel
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$136 per night from 31 May to 1 June
AU$136
31 May - 1 June
includes taxes & fees
9/10 Wonderful! (1,014 reviews)
Breakfast menu was simple but fresh.

Reviewed on 16 May 2026

Spark by Hilton 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 24 May to 25 May
AU$108
24 May - 25 May
includes taxes & fees
8.6/10 Excellent! (1,072 reviews)
The room was clean, and the staff was very welcoming and friendly. The location is especially convenient for truckers or anyone needing a quick overnight stop. The rooms have been partially updated with new flooring and a more modern look, but the walls still need some attention, which made the updates ...

Reviewed on 16 May 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.
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Frequently asked questions

How much does an Old Town Winchester holiday package cost?
Our Old Town Winchester holiday packages, which begin from just AU$9,774, 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.