Old Town Winchester Vacations from ￥283,729

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The Latest Old Town Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Kellogg Conference Hotel at Gallaudet University

Kellogg Conference Hotel at Gallaudet University

3 out of 5
Northeast
Price was ￥345,980, price is now ￥283,729 per person
￥283,729
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
8.2/10 Very Good! (1,001 reviews)
Parking detached from the actual hotel. Location setting is excellent and close to many shops and local

Reviewed on May 12, 2026

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Price was ￥405,506, price is now ￥313,570 per person
￥313,570
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9/10 Wonderful! (1,184 reviews)
The staff was so helpful and great but the beds and pillows were so uncomfortable. The pillows especially were awful and we changed them too. Still bad. Won’t stay there again because we both slept so badly.

Reviewed on May 15, 2026

Eurostars Saint Gregory Dupont Circle Georgetown

Eurostars Saint Gregory Dupont Circle Georgetown

4 out of 5
Downtown Washington D.C.
Price was ￥382,020, price is now ￥303,385 per person
￥303,385
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
8.8/10 Excellent! (1,000 reviews)
Unexpected upgrade at check in. Was much appreciated!

Reviewed on May 16, 2026

InterContinental Washington D.C. - The Wharf by IHG

InterContinental Washington D.C. - The Wharf by IHG

5 out of 5
Southwest
Price was ￥432,296, price is now ￥351,490 per person
￥351,490
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9.4/10 Exceptional! (1,152 reviews)
Excellent location and hotel

Reviewed on May 16, 2026

The River Inn

The River Inn

4 out of 5
Northwest
Price was ￥361,344, price is now ￥302,372 per person
￥302,372
per person
Jul 11 - Jul 17
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Baltimore (BWI)
9.4/10 Exceptional! (1,938 reviews)
Everything and Everyone was great! The restaurant served delicious meals! Close to the Metro and within walking distance to universities, retail and shops!

Reviewed on May 15, 2026

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 ￥19,395 per night from May 25 to May 26
￥19,395
￥21,975 total
May 25 - May 26
includes taxes & fees
9.4/10 Exceptional! (1,005 reviews)
You can’t go wrong staying here. The staff were very friendly. The beds were very comfortable and the room was very clean. This hotel is centrally located so you can park your car and walk around the old town area. This was our second time staying here and it didn’t disappoint. We will definitely ...

Reviewed on May 17, 2026

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 ￥12,168 per night from May 31 to Jun 1
￥12,168
￥13,787 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (1,020 reviews)
Would like to see a bigger breakfast with hot items. The property is very clean and staff are super friendly. This is my third time here and we will be staying again next year.

Reviewed on May 17, 2026

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 ￥16,792 per night from May 24 to May 25
￥16,792
￥18,269 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (860 reviews)
The room was spotless! Bed was so very comfortable. Breakfast was just right!

Reviewed on May 17, 2026

TRU By Hilton Winchester
See all 370 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 ￥283,729, 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.