Winchester Vacations from $423

Book a Hotel + Flight or Car together to unlock savings

Your Winchester Vacation

Known for its small-town feel and rich history, Winchester is the perfect getaway destination. Book one of our Winchester vacation packages and enjoy all that this interesting city has to offer. If sightseeing is on the agenda during your trip to Winchester, visit leading attractions like Shenandoah University, Rock Harbor Golf Course and Museum of the Shenandoah Valley. Stop daydreaming and start adventuring. Browse the wide range of options on Expedia today and put your Winchester vacation plans in motion!

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
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
8.6/10 Excellent! (1,549 reviews)
Great place and close to everything, clean and tidy, but no drinking water available even a coffee machine inside the room.

Reviewed on Jun 3, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (2,025 reviews)
All good. Easy bus links into DC

Reviewed on Jun 4, 2024

YOTEL Washington DC

YOTEL Washington DC

4 out of 5
Northwest
Save 100% on your flight
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
8.4/10 Very Good! (1,468 reviews)
Nice property, clean, and comfortable. Small rooms but perfect for a short stay. Geared more toward younger people.

Reviewed on May 29, 2024

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
8.8/10 Excellent! (1,000 reviews)
Most staff members were nice and helpful. Smooth and easy check-in and out. Rooms are quiet. 'Do not disturb' signs respected.

Reviewed on Jun 2, 2024

Hyatt Place National Harbor

Hyatt Place National Harbor

3 out of 5
Save 100% on your flight
per person
Aug 23 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to Washington (DCA)
9.2/10 Wonderful! (1,491 reviews)
This was my second time staying at this hotel and I loved it. The staff was very nice and accommodating

Reviewed on Jun 3, 2024

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
27,300
Max Temp Winter
40ºF
Max Temp Summer
85ºF
Top Sights
Museum of the Shenandoah Valley, Shenandoah Valley Discovery Museum and Bright Box Theater

Winchester Hotel Deals

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 $98 per night from Jun 24 to Jun 25
$98
$107 total
includes taxes & fees
Jun 24 - Jun 25
8.8/10 Excellent! (1,357 reviews)
"Excellent stay"

Reviewed on May 29, 2024

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 $88 per night from Jun 9 to Jun 10
$88
$96 total
includes taxes & fees
Jun 9 - Jun 10
8.8/10 Excellent! (802 reviews)
"modern, clean, no coffee pot in room"

Reviewed on Jun 3, 2024

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 $68 per night from Jun 17 to Jun 18
$68
$74 total
includes taxes & fees
Jun 17 - Jun 18
7.8/10 Good! (1,068 reviews)
"Nice clean room, bathroom and comfortable bed. Would be great to have scrambled eggs at breakfast instead of hard boiled."

Reviewed on Jun 1, 2024

Travelodge by Wyndham Winchester
See all 1,851 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Perhaps less than you might think — from only $423, 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.