Old Town Winchester Vacations from ￥69,536

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

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The Latest Old Town Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Canopy by Hilton Washington DC The Wharf

Canopy by Hilton Washington DC The Wharf

4 out of 5
The Wharf
Price was ￥89,142, price is now ￥69,536 per person
￥69,536
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Baltimore (BWI)
8.8/10 Excellent! (1,007 reviews)
Clean room Nice staff

Reviewed on Nov 14, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was ￥265,364, price is now ￥200,427 per person
￥200,427
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
18/10 Exceptional! (1,084 reviews)
Room was spotless and comfortable and quiet. All staff were very friendly and helpful. Great location to walk to the Metro and restaurants and the White House!

Reviewed on Oct 28, 2025

Hilton Washington DC Capitol Hill

Hilton Washington DC Capitol Hill

4 out of 5
Northwest
Price was ￥271,642, price is now ￥215,941 per person
￥215,941
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9/10 Wonderful! (1,011 reviews)
Rooms very clean, staff very friendly and professional.

Reviewed on Nov 7, 2025

Fairmont Washington, D.C., Georgetown

Fairmont Washington, D.C., Georgetown

4 out of 5
Northwest
Price was ￥294,948, price is now ￥235,366 per person
￥235,366
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Washington (DCA)
9.4/10 Exceptional! (1,003 reviews)
confortable and Clean room, very well ubicated

Reviewed on Nov 10, 2025

Eaton DC

Eaton DC

4.5 out of 5
Downtown Washington D.C.
Price was ￥94,394, price is now ￥75,352 per person
￥75,352
per person
Jan 5 - Jan 8
found 1 day ago
Roundtrip non-stop flight included
Omaha (OMA) to Washington (DCA)
18.4/10 Exceptional! (1,419 reviews)
Beautiful property and rooms

Reviewed on Nov 1, 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
Fully refundableReserve now, pay when you stay
The price is ￥19,574 per night from Nov 23 to Nov 24
￥19,574
￥22,176 total
Nov 23 - Nov 24
includes taxes & fees
9.2/10 Wonderful! (1,002 reviews)
Nice room, helpful and courteous staff

Reviewed on Nov 12, 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 ￥16,236 per night from Nov 17 to Nov 18
￥16,236
￥17,666 total
Nov 17 - Nov 18
includes taxes & fees
9.2/10 Wonderful! (2,205 reviews)
The room was very clean, well stocked with towels and the bedding was fresh. Staff was very kind and check in/out went quickly. I also enjoy the breakfasts.

Reviewed on Nov 12, 2025

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites Winchester

Comfort Inn & Suites Winchester

2.5 out of 5
195 Kernstown Commons Blvd Winchester VA
Fully refundableReserve now, pay when you stay
The price is ￥15,633 per night from Nov 22 to Nov 23
￥15,633
￥17,011 total
Nov 22 - Nov 23
includes taxes & fees
9.4/10 Exceptional! (1,046 reviews)
The absolute best Comfort Inn in history.

Reviewed on Nov 9, 2025

Comfort Inn & Suites Winchester
See all 371 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 ￥69,536, 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.