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.
Glover Park - Georgetown

Glover Park - Georgetown

4 out of 5
Northwest
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (2,003 reviews)
Clean, safe and location

Reviewed on May 26, 2024

The Graham Georgetown

The Graham Georgetown

4 out of 5
Georgetown
Save 100% on your flight
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.8/10 Excellent! (1,326 reviews)
Not only is the location outstanding, but the staff were the most capable and welcoming i encountered in the DC area. It is an easy walk to some very good bakeries and restsurants as well. Close to the Potomac and to Georgetown shopping.

Reviewed on May 27, 2024

Hamilton Hotel Washington DC

Hamilton Hotel Washington DC

4 out of 5
Downtown Washington D.C.
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
8.6/10 Excellent! (1,512 reviews)
Staff is friendly and helpful

Reviewed on May 26, 2024

Riggs Washington DC

Riggs Washington DC

5 out of 5
Downtown Washington D.C.
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9.4/10 Exceptional! (1,231 reviews)
The staff was pleasant and professional. The property was walking distance to the National Gallery of Art (our primary destination), excellent restaurants and the Metro. Our room had no view, the bathroom was tiny (hard to exit) and our shower was missing half the sliding door. By design? If so, never seen that before. Excellent in- room coffee and the hotel cafe food was also excellent.

Reviewed on May 25, 2024

Sofitel Washington DC Lafayette Square

Sofitel Washington DC Lafayette Square

5 out of 5
Downtown Washington D.C.
per person
Jul. 15 - Jul. 19
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Washington (DCA)
9/10 Wonderful! (1,008 reviews)
The hotel is located at a prefect area and is close to all the landmarks. However the property is old and the room is dusty and both the telephones are not working and full of dust. Gym is small and the facility is old. Coffee machine is not working. Though there is complimentary coffee and tea in lobby it seems the staff does not really check whether it’s finished or not. No late check out available. Highly recommend elsewhere that is cost effective.

Reviewed on May 20, 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 $159 per night from Jun. 2 to Jun. 3
CA $159
CA $173 total
includes taxes & fees
Jun 2 - Jun 3
8.8/10 Excellent! (1,348 reviews)
"Love this hotel. Very clean and fancy for the price. Bed is very comfortable and the layout of the rooms are nice."

Reviewed on May 26, 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! (780 reviews)
"Friendly staff. Water pressure in shower could be a better. A little more attention to cleaning the bathrooms."

Reviewed on May 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 $96 per night from Jun. 9 to Jun. 10
CA $96
CA $104 total
includes taxes & fees
Jun 9 - Jun 10
7.8/10 Good! (1,068 reviews)
"The room was very good. The breakfast was mediocre."

Reviewed on May 25, 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

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winchester vacation package cost?
Perhaps less than you might think — from only CA $987, 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

Other vacations you might like

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