Winchester Vacation Packages

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Your Winchester Vacation

The rich history and small-town feel are just the start of the things Winchester has on offer. Experience the best of this city your way with a tailor-made Winchester vacation package. You'll want to do some exploring during your trip to Winchester. Find time for big-name attractions such as Shenandoah University, Museum of the Shenandoah Valley and Apple Blossom Mall. Whatever your travel plans or the size of your budget, organizing your ultimate tailored Winchester vacation is easy with Expedia.

Top Winchester Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hampton Inn & Suites Baltimore Inner Harbor

Hampton Inn & Suites Baltimore Inner Harbor

2.5 out of 5
Downtown Baltimore
per person
Sep. 12 - Sep. 16
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Baltimore (BWI)
8.6/10 Excellent! (1,000 reviews)
The breakfast was awesome! Lots of choices hot and cold alike: pleasantly surprised with the height of the showerhead and the water pressure. The only reason I did not get five stars is because it’s valet parking. For there’s no parking on site.( again downtown so maybe this is not surprising) There is a parking garage down the street.

Reviewed on Jun. 16, 2024

InterContinental Washington D.C. - The Wharf, an IHG Hotel

InterContinental Washington D.C. - The Wharf, an IHG Hotel

5 out of 5
The Wharf
Save 100% on your flight
per person
Aug. 6 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Washington (DCA)
9.2/10 Wonderful! (1,020 reviews)
Amazing place to stay

Reviewed on Jun. 19, 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. 6 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Washington (DCA)
8.8/10 Excellent! (1,000 reviews)
Nice comfortable room; wonderful bed linens. Good hotel for dog friendliness, nice parks nearby.

Reviewed on Jun. 18, 2024

Kimpton George Hotel, an IHG Hotel

Kimpton George Hotel, an IHG Hotel

4.5 out of 5
Northwest
per person
Aug. 6 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Washington (DCA)
9/10 Wonderful! (1,001 reviews)
Short walk to Capitol Hill and Georgetown Law. Great hotel and rooms. Restaurant in the lobby. Free wine with check in. Very friendly staff!

Reviewed on Jun. 18, 2024

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Aug. 6 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Detroit (DTW) to Washington (DCA)
9.4/10 Exceptional! (1,252 reviews)
Great beds. Nice updated bathroom.

Reviewed on Jun. 15, 2024

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 CA $147 per night from Jun. 23 to Jun. 24
CA $147
CA $160 total
includes taxes & fees
Jun 23 - Jun 24
8.8/10 Excellent! (1,385 reviews)
Comfortable room at a fair price
"Great value stay for an overnight on a road trip. New hotel with comfortable rooms, friendly service, and thoughtful amenities. Would choose again when I am in the area!"

Reviewed on Jun. 15, 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 CA $117 per night from Jun. 23 to Jun. 24
CA $117
CA $127 total
includes taxes & fees
Jun 23 - Jun 24
8.8/10 Excellent! (820 reviews)
"Staff was awesome! The room was very clean and the complimentary breakfast was way better than we expected! Would definitely stay there again!"

Reviewed on Jun. 13, 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 CA $89 per night from Jul. 2 to Jul. 3
CA $89
CA $97 total
includes taxes & fees
Jul 2 - Jul 3
7.8/10 Good! (1,077 reviews)
"It was a well kept hotel. Clean and comfortable"

Reviewed on Jun. 16, 2024

Travelodge by Wyndham Winchester
See all 1,853 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Perhaps less than you might think — from only CA $687, 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(1 review)

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

Museum of the Shenandoah Valley
Image for Handley Regional Library

Handley Regional Library

5/5(1 review)

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

Handley Regional Library
Image for Shenandoah University

Shenandoah University

4/5(1 review)

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.