Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

Choose two or more items and save on your trip:
    Plan, book, travel with confidence
  • payments icon
    Better together
    Save up to NZ$545 when you book a flight and hotel together*
  • lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
  • lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

Our pick of the best Winchester Hotel Deals

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 NZ$122 per night from 2 Jun to 3 Jun
NZ$122
per night
2 Jun - 3 Jun
7.8/10 Good! (1,066 reviews)
"great"

Reviewed on 13 May 2024

Travelodge by Wyndham Winchester
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 NZ$194 per night from 26 May to 27 May
NZ$194
per night
26 May - 27 May
8.8/10 Excellent! (1,338 reviews)
Great stay!
"Check in was fast and easy. Fresh coffee and lemon water greeted us in the entrence. Our room was super cozy and modern. Lots of plugs for devices. Desk area with chair for business use. Both beds were super comfy. Room was quiet and just what we needed after a long day of travel. Work out facilities ..."

Reviewed on 20 May 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 NZ$150 per night from 2 Jun to 3 Jun
NZ$150
per night
2 Jun - 3 Jun
8.8/10 Excellent! (768 reviews)
Great place
"Pool is cold, staff is super nice. Place is clean and very nice lots near it for food mall is only 8 min away. Breakfast was ok. Have stayed here several times and will continue to stay here as needed."

Reviewed on 19 May 2024

Microtel Inn & Suites by Wyndham 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.

Frequently asked questions

How much does a Winchester holiday package cost?
Perhaps less than you might think — from only , 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 holiday 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 Centre 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 holiday?
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 holiday package is the most convenient way to organise 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 holiday 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 holiday 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

What to do in Winchester

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