Old Town Winchester Holidays from AU$2,412

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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.
La Quinta Inn & Suites by Wyndham Baltimore Downtown

La Quinta Inn & Suites by Wyndham Baltimore Downtown

3 out of 5
Downtown Baltimore
Price was AU$2,617, price is now AU$2,412 per person
AU$2,412
per person
5 Feb - 12 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
5.2/10 (1,000 reviews)
Room was clean staff was Helpful and courteous.

Reviewed on 29 Dec 2025

Pendry Baltimore

Pendry Baltimore

5 out of 5
Fells Point
Price was AU$4,973, price is now AU$4,123 per person
AU$4,123
per person
5 Feb - 12 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
I didn't use these amenities.

Reviewed on 27 Dec 2025

Graduate by Hilton Annapolis

Graduate by Hilton Annapolis

4 out of 5
Price was AU$3,146, price is now AU$2,748 per person
AU$2,748
per person
5 Feb - 12 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
9.4/10 Exceptional! (1,000 reviews)
Pleasant staff. Good location to walk to restaurants, shops.

Reviewed on 30 Dec 2025

Lord Baltimore Hotel

Lord Baltimore Hotel

3.5 out of 5
Downtown Baltimore
Price was AU$3,059, price is now AU$2,799 per person
AU$2,799
per person
5 Feb - 12 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
8.2/10 Very Good! (2,362 reviews)
Elevator situation was frustrating.

Reviewed on 27 Dec 2025

Hyatt Place Baltimore Inner Harbor

Hyatt Place Baltimore Inner Harbor

3.5 out of 5
Harbor East
Price was AU$2,949, price is now AU$2,717 per person
AU$2,717
per person
5 Feb - 12 Feb
found 1 day ago
Return flight included
Sydney (SYD) to Baltimore (BWI)
8.2/10 Very Good! (2,405 reviews)
Very family friendly. My girls enjoyed going to breakfast in the morning and the pool. Staff were very nice.

Reviewed on 29 Dec 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$214 per night from 6 Jan to 7 Jan
AU$214
6 Jan - 7 Jan 2026
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
I love this hotel. I have stayed here once or twice a year over the past few years for the affordability, cleanliness, pool, hot tub, and location on my way up north. This past stay I noticed they are doing their best to keep up with increasing maintenance demands and decreasing profits.

Reviewed on 29 Dec 2025

The George Washington Hotel, A Wyndham Grand Hotel
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$129 per night from 4 Jan to 5 Jan
AU$129
4 Jan - 5 Jan 2026
includes taxes & fees
9/10 Wonderful! (1,402 reviews)
Great staff. Clean room. Excellent location

Reviewed on 26 Dec 2025

Microtel 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$110 per night from 1 Jan to 2 Jan
AU$110
1 Jan - 2 Jan 2026
includes taxes & fees
8.4/10 Very Good! (1,080 reviews)
All of the above mentioned and a great, nutritious and varied breakfast. Also, both regular and decaf coffee were available in the breakfast area whenever I wanted it. Lastly, plentiful parking.

Reviewed on 27 Dec 2025

Travelodge by Wyndham Winchester
See all 361 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$2,412, 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.