Winchester Vacations from ￥365,183

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The Latest Winchester Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
per person
Jun 16 - Jun 21
Roundtrip flight included
Fukuoka (FUK) to Washington (DCA)
8.6/10 Excellent! (1,497 reviews)
A nice stay, several parks nearby

Reviewed on May 10, 2024

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
Jun 16 - Jun 21
Roundtrip flight included
Fukuoka (FUK) to Washington (DCA)
9/10 Wonderful! (1,006 reviews)
Comfortable and quiet room. Close to the White House and the National Mall. Valet Parking. Delicious breakfast with a French Flair.

Reviewed on May 5, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Jun 16 - Jun 21
Roundtrip flight included
Fukuoka (FUK) to Washington (DCA)
8.8/10 Excellent! (1,994 reviews)
It has the most amazing gym!

Reviewed on May 8, 2024

Hyatt Place National Harbor

Hyatt Place National Harbor

3 out of 5
per person
Jun 16 - Jun 21
Roundtrip flight included
Fukuoka (FUK) to Washington (DCA)
9.2/10 Wonderful! (1,479 reviews)
This is one of the best hotels I have stayed in. Super clean, not noisy, great breakfast. Highly recommend this property. I will definitely go back.

Reviewed on May 8, 2024

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
per person
Jun 16 - Jun 21
Roundtrip flight included
Fukuoka (FUK) to Washington (DCA)
8.4/10 Very Good! (1,445 reviews)
Great experience with checking in and the hotel being clean and comfortable! Would definitely stay in again.

Reviewed on May 9, 2024

Winchester Hotel Deals

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 ￥13,074 per night from Jun 2 to Jun 3
￥13,074
per night
Jun 2 - Jun 3
8.8/10 Excellent! (745 reviews)
Good
"Good place to stay"

Reviewed on May 8, 2024

Microtel Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
La Quinta Inn & Suites by Wyndham Winchester
2.5 out of 5
1055 Millwood Pike, Route 50 East, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is ￥17,711 per night from May 12 to May 13
￥17,711
per night
May 12 - May 13
8.8/10 Excellent! (1,304 reviews)
"Very clean, very Nice and roomy. Plenty to do in the area with restaurants and activities.. I will definitely make this one of my favorite stops."

Reviewed on May 7, 2024

La Quinta Inn & Suites by Wyndham Winchester
Comfort Inn & Suites
Comfort Inn & Suites
2.5 out of 5
195 Kernstown Commons Blvd, Winchester, VA
Fully refundableReserve now, pay when you stay
The price is ￥15,916 per night from May 19 to May 20
￥15,916
per night
May 19 - May 20
9.4/10 Exceptional! (916 reviews)
"Nice breakfast selection"

Reviewed on May 8, 2024

Comfort Inn & Suites
See all 1,893 properties in 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 a Winchester vacation package cost?
Perhaps less than you might think — from only ￥365,183, in fact! By bundling flights, hotels and car rentals into a custom-made travel package, your getaway to Winchester is just a few clicks away.
How do I get a cheap travel package to Winchester?
You’ll save a pile of money if you combine your flights, car rentals and hotels into a Winchester vacation package. Sometimes cheap means fewer options. But that’s not the case with Expedia. We offer more than 550 partner airlines and 1,000,000 hotels all over the world, which means you’ll always have plenty of variety to choose from. Like to save even more? Add some fun activities to your package deal and unlock even more discounts! After all, travel is about more than simply getting to your destination.
Where should I stay in Winchester?
A getaway to Winchester wouldn’t be complete without stopping by Shenandoah University, Winchester Medical Center and Museum of the Shenandoah Valley. Stay near these top sights and make sightseeing simple.
What are the top hotels in Winchester?
Many people opt to stay at La Quinta Inn & Suites by Wyndham Winchester in Old Town Winchester. If it’s your very first time in Winchester, you’ll be given a warm welcome here.
How far in advance should I book my Winchester vacation?
Reserving your seat early with Expedia means one less thing to worry about. Many air carriers display prices up to a year in advance. Usually, this is the cheapest time to book. If circumstances have left you booking late, great deals to Winchester sometimes become available a few weeks before departure.
What does an Expedia Winchester travel package include?
With Expedia, you can choose any combination of car rentals, flights and hotels to build your ideal Winchester travel package. Once you’ve made your booking, you can add on fun stuff like day tours and activities. Don’t forget, the more you bundle, the more you’ll save!
What should I know before booking a Winchester travel package?
Bundling your bookings into a Winchester vacation package is the most convenient way to organize your trip. Not only that, you’ll get great discounts just for combining your flights, hotels and car rentals. Once you’ve booked, why not add on an activity or a tour?
Can I choose my airline with a Winchester Expedia vacation package?
Yes — and it’s easy too. Expedia has access to more than 550 partner airlines around the world. Our packages give you the freedom to take your pick of available flight, hotel or activity options that fit your needs.
If I'm not able to travel, can I cancel my Winchester vacation package?
Yes, it’s possible to cancel your Winchester booking if your travel plans have been upended. Whether you’ll incur a fee or not depends on your hotel, airline or car rental company. It may be possible to change or cancel for free if you booked in the last 24 hours. Visit our Customer Service Portal for more information.

Discover the most popular places to visit in Winchester

Image for Museum of the Shenandoah Valley

Museum of the Shenandoah Valley

5/5(19 reviews)

You can spend time exploring the galleries in Museum of the Shenandoah Valley during your trip to Winchester. Check out the charming coffeehouses or top-notch restaurants in this walkable area.

Museum of the Shenandoah Valley
Image for Handley Regional Library

Handley Regional Library

5/5(2 reviews)

After visiting Handley Regional Library, make a plan to see the other sights and activities in Winchester. Check out the top-notch restaurants or charming coffeehouses in this walkable area.

Handley Regional Library
Image for Shenandoah University

Shenandoah University

4.5/5(69 reviews)

Enjoy the collegiate vibe when you visit Shenandoah University, during your trip to Winchester. While in this walkable area, you can savor the top-notch restaurants.

Shenandoah University

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