Old Town Winchester Holidays from AU$2,686

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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.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
8.2/10 Very Good! (455 reviews)
We enjoyed our stay at the hotel:) people were very polite:)

Reviewed on 21 Dec. 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Northwest
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
8.8/10 Excellent! (1,524 reviews)
I loved the property and its proximity to M St & Wisconsin Ave, the main streets in Georgetown. Their checkin is not until 4pm which hindered our ability to get to our function, but the property, room with a balcony, rooftop & speakeasy bars were great!

Reviewed on 19 Dec. 2024

Arlo Washington DC

Arlo Washington DC

4 out of 5
Northwest
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
8.6/10 Excellent! (10 reviews)
Quick, easy check-in, nicely appointed room. Really enjoyed our stay.

Reviewed on 26 Dec. 2024

The Melrose Georgetown Hotel

The Melrose Georgetown Hotel

4 out of 5
Northwest
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
8.8/10 Excellent! (2,042 reviews)
Great location, spacious room, bathroom functional but slightly dated. Great stay overall!

Reviewed on 24 Dec. 2024

AC Hotel by Marriott Washington DC Downtown

AC Hotel by Marriott Washington DC Downtown

4 out of 5
Downtown Washington D.C.
per person
3 Mar - 10 Mar
found 1 day ago
Return direct flight included
Sydney (SYD) to Washington (DCA)
9.2/10 Wonderful! (845 reviews)
Great stay great staff great location

Reviewed on 5 Dec. 2024

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$230 per night from 2 Jan to 3 Jan
AU$230
includes taxes & fees
2 Jan - 3 Jan 2025
9.2/10 Wonderful! (1,000 reviews)
"Lovely stay, staff were kind and helpful, parking was easy and plenty of cool places to dine within walking distance. We love coming here."

Reviewed on 16 Dec. 2024

The George Washington Hotel, A Wyndham Grand Hotel
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is AU$186 per night from 7 Jan to 8 Jan
AU$186
includes taxes & fees
7 Jan - 8 Jan 2025
9/10 Wonderful! (1,754 reviews)
"We have stayed here several times. It is convenient and quiet and safe."

Reviewed on 24 Dec. 2024

La Quinta Inn & Suites by Wyndham Winchester
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 1 Jan to 2 Jan
AU$132
includes taxes & fees
1 Jan - 2 Jan 2025
9/10 Wonderful! (1,079 reviews)
"Very friendly staff."

Reviewed on 24 Dec. 2024

Microtel Inn & Suites by Wyndham Winchester
See all 342 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$2,686, 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.