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.
The Madison Hotel

The Madison Hotel

4.5 out of 5
Downtown Washington D.C.
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,003 reviews)
Friendly check in and door service-very welcoming.

Reviewed on May 14, 2024

Kimpton Hotel Monaco Washington DC, an IHG Hotel

Kimpton Hotel Monaco Washington DC, an IHG Hotel

4.5 out of 5
Downtown Washington D.C.
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.6/10 Excellent! (1,000 reviews)
Excellent location for visiting the Mall and all of the museums. Room was clean and large, but suffered from being close to the bar/entertainment area. Staff was always friendly and very accommodating but I wish there was a smaller & quicker food option, like a nice, simple coffee bar. My only complaint/suggestion...install some towel bars in the bathroom to hang used towels.

Reviewed on May 22, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
per person
Aug. 4 - Aug. 9
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (1,326 reviews)
The staff was very friendly.

Reviewed on May 20, 2024

Tysons Corner Marriott

Tysons Corner Marriott

4 out of 5
per person
Jun. 27 - Jul. 3
Roundtrip flight included
Toronto (YYZ) to Washington (DCA)
8.8/10 Excellent! (1,000 reviews)
I stayed at the property for a business event. It was very nice but I probably wouldn’t stay again for that same price. I feel it was a little overpriced

Reviewed on May 20, 2024

Hyatt House Washington DC/The Wharf

Hyatt House Washington DC/The Wharf

3.5 out of 5
The Wharf
per person
Jun. 21 - Jun. 24
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,246 reviews)
Overall, this was a good stay. I was a little disappointed when we first got to our room; there were crumbs from the previous person that was there on the floor. It was also not very clear, but this property does not offer room service either. And the roof was closed, which was a little disappointing; was. not planning on swimming, but did want to go out there and hang out and read a book. I did, however, enjoy how close it was to everything. If you are on vacation, this is a great place to stay; close to great sites and food options.

Reviewed on May 22, 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 $157 per night from May 26 to May 27
CA $157
CA $170 total
includes taxes & fees
May 26 - May 27
8.8/10 Excellent! (1,333 reviews)
"The only complaint is there is no curtain to hide the frosted window panel into the sleeping area. Therefore no complete privacy when showering while children are awake and light from that comes directly to head of the bed if you wait till they are asleep."

Reviewed on May 20, 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 $115 per night from Jun. 2 to Jun. 3
CA $115
CA $125 total
includes taxes & fees
Jun 2 - Jun 3
8.8/10 Excellent! (771 reviews)
"Its was a really nice hotel the people were friendly 🙂 very clean and a reasonable price i would stay there again without a doubt thank you"

Reviewed on May 21, 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 $93 per night from Jun. 2 to Jun. 3
CA $93
CA $102 total
includes taxes & fees
Jun 2 - Jun 3
7.8/10 Good! (1,063 reviews)
"nice place, clean but in desperate need of update."

Reviewed on May 18, 2024

Travelodge by Wyndham Winchester
See all 1,857 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 $690, 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.