Old Town Winchester Holidays from AU$411

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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.
Beacon Hotel & Corporate Quarters

Beacon Hotel & Corporate Quarters

3.5 out of 5
Downtown Washington D.C.
per person
28 Sept - 30 Sept
found 1 day ago
Return flight included
Orlando (MCO) to Washington (WAS)
7.6/10 Good! (1,027 reviews)
Nice facility. Expected a slightly nicer bathroom for the price

Reviewed on 26 Jul. 2025

The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
28 Sept - 30 Sept
found 1 day ago
Return flight included
Orlando (MCO) to Washington (DCA)
8.6/10 Excellent! (1,007 reviews)
My stay was very pleasant

Reviewed on 27 Jul. 2025

SIXTY DC

SIXTY DC

2 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
28 Sept - 30 Sept
found 1 day ago
Return flight included
Orlando (MCO) to Washington (DCA)
10/10 Exceptional! (12 reviews)
Very nice and clean hotel, very friendly team, neat and impressive technology equipped rooms, I would highly recommend it to friends and family

Reviewed on 25 Jul. 2025

Hotel Washington

Hotel Washington

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
28 Sept - 30 Sept
found 1 day ago
Return flight included
Orlando (MCO) to Washington (DCA)
9/10 Wonderful! (2,272 reviews)
It is a very swanky place. If you’re traveling as a family it is a great location. Please note that the shower in some rooms (like ours) does not have a solid door. It does have a cloudy glass door on the shower, but that is in direct view of on of the beds.. we had to stay on one side of the room each time one of us took a shower. Other than that it was great!!

Reviewed on 29 Jul. 2025

Hotel Madera

Hotel Madera

4 out of 5
Downtown Washington D.C.
per person
28 Sept - 30 Sept
found 1 day ago
Return flight included
Orlando (MCO) to Washington (DCA)
9.2/10 Wonderful! (1,006 reviews)
Very comfortable bed and pillows, clean bath and huuuge space! Just one uncomfortable thing was slowly elevator.

Reviewed on 30 Jul. 2025

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$222 per night from 25 Aug to 26 Aug
AU$222
25 Aug - 26 Aug
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
"We stayed 3 nights at this hotel. It was really nice. Clean, convenient to shopping and restaurants in the Old City. Staff was very friendly and helpful. The bar was a great place to visit and service was great. My husband used the pool and hot tub and thought it was clean and well maintained. Parking ..."

Reviewed on 30 Jul. 2025

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$163 per night from 1 Sept to 2 Sept
AU$163
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (2,091 reviews)
"Stay at a lot of places. For the price, this was well worth it. Clean, nice rooms, very good coffee. Breakfast was a little lame but to be expected. Still worth it"

Reviewed on 29 Jul. 2025

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$133 per night from 1 Sept to 2 Sept
AU$133
1 Sept - 2 Sept
includes taxes & fees
9/10 Wonderful! (1,322 reviews)
"Easy access to hotel, stores, restaurants/food."

Reviewed on 30 Jul. 2025

Microtel Inn & Suites by Wyndham Winchester
See all 352 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$411, 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.