Old Town Winchester Vacations

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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 ₩173,828 per night from Aug 31 to Sep 1
₩173,828
₩196,949 total
Aug 31 - Sep 1
includes taxes & fees
9.2/10 Wonderful! (1,009 reviews)
"Great time relaxing in old town Winchester"

Reviewed on Aug 24, 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 ₩142,564 per night from Sep 1 to Sep 2
₩142,564
₩155,111 total
Sep 1 - Sep 2
includes taxes & fees
9.2/10 Wonderful! (2,136 reviews)
"The bedroom was clean. Some area a bit older looking but good. Hall ways a little smelly like needs carpets refreshed. But not all that bad.."

Reviewed on Aug 25, 2025

La Quinta Inn & Suites by Wyndham Winchester
Holiday Inn Winchester Se-Historic Gateway by IHG

Holiday Inn Winchester Se-Historic Gateway by IHG

3 out of 5
333 Front Royal Pike, Winchester, VA
Fully refundable
The price is ₩113,940 per night from Sep 7 to Sep 8
₩113,940
₩128,141 total
Sep 7 - Sep 8
includes taxes & fees
9/10 Wonderful! (1,007 reviews)
"Clean and staff was great."

Reviewed on Aug 23, 2025

Holiday Inn Winchester Se-Historic Gateway by IHG
See all 357 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.

Frequently asked questions

How much does an Old Town Winchester vacation package cost?
Our Old Town Winchester vacation packages, which begin from just , 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 vacation 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 vacation in Old Town Winchester wouldn't be complete without checking out Shenandoah University, Winchester Medical Center 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 favorite with lots of travelers.
How far in advance should I book my Old Town Winchester vacation?
You'll be rewarded with the widest variety at the cheapest prices by booking your Old Town Winchester vacation 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 vacation!
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 favorite 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 vacation package?
With a vacation 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 vacation package?
Whether it's your hotel, flight or rental car, yes, you can cancel or amend it. Booked your Old Town Winchester vacation 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.