Old Town Winchester Vacations from ￥239,528

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to ￥45,448 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    Rest easy

    Plan, book, and manage your trip all in one place

The Latest Old Town Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
The Wharf
Price was ￥291,484, price is now ￥239,528 per person
￥239,528
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9.4/10 Exceptional! (1,010 reviews)
Great stay! Large room, comfortable bed and good food options.

Reviewed on Sep 19, 2025

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Price was ￥324,213, price is now ￥248,425 per person
￥248,425
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9.2/10 Wonderful! (1,413 reviews)
Gorgeous bar, walking distance to main attractions

Reviewed on Sep 23, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was ￥337,237, price is now ￥261,897 per person
￥261,897
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
9/10 Wonderful! (1,044 reviews)
We were upgraded for free on arrival. Our room and the view were beautiful. We will absolutely stay here in a heartbeat again!

Reviewed on Sep 23, 2025

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Price was ￥320,914, price is now ￥259,841 per person
￥259,841
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9/10 Wonderful! (1,003 reviews)
Clean Room,nice views

Reviewed on Sep 26, 2025

The Watergate Hotel

The Watergate Hotel

5 out of 5
Northwest
Price was ￥303,377, price is now ￥248,060 per person
￥248,060
per person
Oct 27 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (WAS)
8.8/10 Excellent! (1,011 reviews)
Staff was very accommodating

Reviewed on Sep 23, 2025

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
The price is ￥18,933 per night from Oct 5 to Oct 6
￥18,933
￥21,450 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (1,010 reviews)
"The beauty of the property to begin with. Old world charm but modernized without detracting from the original character. The grand mailbox, each floor having a mailbox which directly connects with and is fed by gravity to the “grand” collection box on the ground floor! Beautiful! The basement pool ..."

Reviewed on Sep 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 ￥16,191 per night from Oct 5 to Oct 6
￥16,191
￥17,616 total
Oct 5 - Oct 6
includes taxes & fees
9.2/10 Wonderful! (2,166 reviews)
"Friendly front desk..needed additional pillow and blanket ..got immediate response"

Reviewed on Sep 23, 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 ￥12,557 per night from Oct 26 to Oct 27
￥12,557
￥13,663 total
Oct 26 - Oct 27
includes taxes & fees
9/10 Wonderful! (1,346 reviews)
"Very nice place to stay. Everything is perfectly placed and the amenities were good."

Reviewed on Sep 21, 2025

Microtel Inn & Suites by Wyndham Winchester
See all 362 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 ￥239,528, 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.