Old Town Winchester Vacations from ￥166,964

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The Latest Old Town Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hotel Arboretum

Hotel Arboretum

2 out of 5
Northeast
Price was ￥199,798, price is now ￥166,964 per person
￥166,964
per person
Jan 30 - Feb 4
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
8/10 Very Good! (1,178 reviews)
Although the facility was undergoing renovations, the room itself was clean and comfortable. There were no rugs or carpets on the floor. I preferred them bare, much more hygienic so I was very happy. The pillows were exceptionally comfortable and the beds just as much! Also included were a decent size refrigerator and microwave. It was everything I expected and the price was beyond incredible. Will definitely be returning!

Reviewed on Dec 29, 2025

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was ￥275,864, price is now ￥213,940 per person
￥213,940
per person
Jan 30 - Feb 4
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9/10 Wonderful! (1,084 reviews)
Did not eat breakfast at the hotel.

Reviewed on Dec 25, 2025

Embassy Suites by Hilton Washington D.C. – Convention Center

Embassy Suites by Hilton Washington D.C. – Convention Center

3.5 out of 5
Downtown Washington D.C.
Price was ￥249,108, price is now ￥198,890 per person
￥198,890
per person
Jan 30 - Feb 4
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9.2/10 Wonderful! (2,031 reviews)
Very nice clean spacious room for my husband and I.

Reviewed on Dec 30, 2025

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was ￥228,629, price is now ￥185,965 per person
￥185,965
per person
Jan 30 - Feb 4
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
8.6/10 Excellent! (1,008 reviews)
Clean room and prompt response to room provision request. Great customer service. Location close to many good dining options.

Reviewed on Dec 27, 2025

Hampton Inn & Suites Washington DC-Navy Yard

Hampton Inn & Suites Washington DC-Navy Yard

3 out of 5
Navy Yard
Price was ￥224,185, price is now ￥186,378 per person
￥186,378
per person
Jan 30 - Feb 4
just found
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9/10 Wonderful! (1,004 reviews)
This is a wonderful hotel. The staff (especially Christian) were friendly and helpful. The room was clean and comfortable. The breakfast each morning was hot and plentiful. I would absolutely stay here again. It is a great location with the metro station a few steps away.

Reviewed on Dec 30, 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 ￥19,754 per night from Jan 6 to Jan 7
￥19,754
￥22,382 total
Jan 6 - Jan 7, 2026
includes taxes & fees
9.2/10 Wonderful! (1,008 reviews)
No wait

Reviewed on Dec 28, 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 ￥12,353 per night from Jan 4 to Jan 5
￥12,353
￥13,440 total
Jan 4 - Jan 5, 2026
includes taxes & fees
9/10 Wonderful! (1,405 reviews)
Great price clean and friendly

Reviewed on Dec 28, 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 ￥10,606 per night from Jan 1 to Jan 2
￥10,606
￥11,539 total
Jan 1 - Jan 2, 2026
includes taxes & fees
8.4/10 Very Good! (1,081 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 Dec 27, 2025

Travelodge 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 ￥166,964, 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.