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 NT$4,096 per night from Jun 15 to Jun 16
NT$4,096
NT$4,641 total
Jun 15 - Jun 16
includes taxes & fees
9.4/10 Exceptional! (1,002 reviews)
"Great old hotel located in the downtown neighborhood. Room was large with a great bathroom. This is always our first choice when visiting Winchester"

Reviewed on 2026/5/28

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 NT$2,797 per night from Jun 22 to Jun 23
NT$2,797
NT$3,169 total
Jun 22 - Jun 23
includes taxes & fees
9/10 Wonderful! (1,016 reviews)
"Clean room, friendly staff. A light breakfast that wasn't anything really special. Traffic in the area around the hotel can be intense, especially if you need to make a left turn on S. Pleasant Valley Road on the way out."

Reviewed on 2026/5/29

Spark by Hilton Winchester
TRU By Hilton Winchester

TRU By Hilton Winchester

2.5 out of 5
118 Mercedes Court Winchester VA
Fully refundableReserve now, pay when you stay
The price is NT$3,712 per night from Jun 14 to Jun 15
NT$3,712
NT$4,038 total
Jun 14 - Jun 15
includes taxes & fees
9/10 Wonderful! (896 reviews)
"This was a great place to stay with our family as we were headed to Boston. Exceptionally clean! Staff was very friendly. Breakfast had several options."

Reviewed on 2026/5/29

TRU By Hilton Winchester
See all 369 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.

Discover the most popular places to visit in Old Town Winchester

Jim Barnett Park

Jim Barnett Park

4/5(1 review)

Explore the great outdoors at Jim Barnett Park, a lovely green space in Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Jim Barnett Park

Patsy Cline Historic House

4/5(19 reviews)

You can find out about the history of Winchester with a stop at Patsy Cline Historic House. While in this walkable area, you can savor the top-notch restaurants.

Patsy Cline Historic House

Rock Harbor Golf Course

3.5/5(3 reviews)

Enjoy a round of golf in Winchester at Rock Harbor Golf Course. While in this walkable area, you can savor the top-notch restaurants.

Rock Harbor Golf Course
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.