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

Prices and availability subject to change. Additional terms may apply.
The St. Gregory Hotel

The St. Gregory Hotel

4 out of 5
Downtown Washington D.C.
per person
Jul. 11 - Jul. 18
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
8.6/10 Excellent! (1,012 reviews)
The Desk Staff was welcoming and knowledgable. Valet Service was courteous responsive.

Reviewed on Apr. 17, 2024

Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
Save 100% on your flight
per person
Jul. 11 - Jul. 18
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
8.8/10 Excellent! (1,952 reviews)
I stayed for 3 days, never had housekeeping come. I asked for towel, the man had an attitude with me. Otherwise the place was great. I always tip housekeeping, not this time

Reviewed on Apr. 24, 2024

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
per person
Jul. 11 - Jul. 18
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
8.6/10 Excellent! (1,449 reviews)
We were disappointed that there was no valet parking. It was difficult to find parking.

Reviewed on Apr. 25, 2024

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
Save 100% on your flight
per person
Jul. 11 - Jul. 18
Roundtrip flight included
Ottawa (YOW) to Washington (DCA)
9.4/10 Exceptional! (1,226 reviews)
Great location. Comfortable. Pricy.

Reviewed on Apr. 23, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
per person
Jun. 16 - Jun. 19
Roundtrip non-stop flight included
Ottawa (YOW) to Washington (DCA)
8.8/10 Excellent! (1,300 reviews)
Just perfect for dc

Reviewed on Apr. 23, 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 $148 per night from Apr. 28 to Apr. 29
CA $148
CA $162 total
includes taxes & fees
Apr 28 - Apr 29
8.8/10 Excellent! (1,279 reviews)
"Nicer hotel. Felt safe and was clean. The check in clerk was okay but quick and brusk with instructions. Not overly friendly. She was more interested in another employee who was trying to talk with her at the same time."

Reviewed on Apr. 23, 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 $99 per night from May 12 to May 13
CA $99
CA $107 total
includes taxes & fees
May 12 - May 13
8.8/10 Excellent! (726 reviews)
"Great hotel! Staff is excellent and rooms are clean."

Reviewed on Apr. 24, 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 $101 per night from Apr. 28 to Apr. 29
CA $101
CA $110 total
includes taxes & fees
Apr 28 - Apr 29
7.8/10 Good! (1,054 reviews)
"Very clean and convenient. Building a bit run down and coffee was weak with limited food but that’s about what was expected for the price. I’d stay again"

Reviewed on Apr. 23, 2024

Travelodge by Wyndham Winchester
See all 1,878 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.

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Frequently asked questions

How much does a Winchester vacation package cost?
Perhaps less than you might think — from only CA $1,257, 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 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(1 review)

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(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

What to do in Winchester

Image for Shenandoah Tour: Self-Guided Drive

Shenandoah Tour: Self-Guided Drive

CA $21
Per adult
96% of travellers recommend
Shenandoah Tour: Self-Guided Drive
See all activities in Winchester

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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.