Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together
    Save up to NZ$545 when you book a flight and hotel together*
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    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Plan, book, and manage your trip all in one place

Our pick of the best Winchester Hotel Deals

Best Western Jacksonville Inn
Best Western Jacksonville Inn
2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
The price is NZ$133 per night from 13 May to 14 May
NZ$133
per night
13 May - 14 May
8.4/10 Very Good! (535 reviews)
One night stay
"Our stay was okay. Breakfast was awful. We were there for one night for a baseball tournament. The pool was so crowded we didn't get a chance to use it. The room itself was comfortable but small."

Reviewed on 7 Apr. 2024

Best Western Jacksonville Inn
Sleep Inn & Suites
Sleep Inn & Suites
2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
The price is NZ$164 per night from 19 May to 20 May
NZ$164
per night
19 May - 20 May
9.2/10 Wonderful! (380 reviews)
"Clean and organized"

Reviewed on 7 May 2024

Sleep Inn & Suites
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
2.5 out of 5
2501 Holliday Lane, Jacksonville, IL
Fully refundable
The price is NZ$157 per night from 19 May to 20 May
NZ$157
per night
19 May - 20 May
7.8/10 Good! (336 reviews)
"We had a major issue with my mother's room and the manager took action and took care of it. We appreciate it!"

Reviewed on 11 Apr. 2024

Holiday Inn Express Hotel & Suites Jacksonville, an IHG Hotel
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?
Live it up in Winchester from just . We offer a wonderful selection of flights, rental cars and hotels to suit your travel style. Land even more discounts when you add a few sightseeing tours to your package.
How do I get a cheap travel package to Winchester?
Secure flights that fit your schedule, add a hotel room to your booking and watch the savings grow with a Winchester holiday package. It’s as simple as that! From hotels and flights to rental cars and tours, Expedia is where your cheap getaway begins. And with over 550 air carriers and 1 000 000 hotels all over the world to pick from, you’ll never be short of choice.
How far in advance should I book my Winchester holiday?
You’ll be rewarded with the biggest variety at the cheapest prices by booking your Winchester holiday nice and early. Air carriers usually advertise tickets around 12 months before departure, so reserve your spot ASAP. That being said, Expedia is committed to giving you the best bargains around, so it’s never a bad time to book your dream holiday!
What does an Expedia Winchester travel package include?
Rental cars, flights and hotels — you’ll discover them all here. With Expedia, you can create your Winchester travel package just how you like it. All you have to do is work out just what you need. Once you’ve made your booking, you can add extras like activities and tours. The more you bundle, the bigger the savings!
What should I know before booking a Winchester travel package?
Our prices are always low. However, you’ll grab an even better deal when you book your flights, hotels and car rentals together. With an Expedia package, you’ll get transparent pricing and a huge range of choice.
Can I choose my airline with a Winchester Expedia holiday package?
Expedia has access to more than 550 partner airlines worldwide, so you sure can! Just select your favourite carrier and create the perfect Winchester holiday.
If I'm not able to travel, can I cancel my Winchester holiday package?
We get that life can throw you the odd curveball. If you’ve booked a Winchester holiday package and have to change or cancel it, we can help. We suggest browsing our Customer Service Portal first for information. But generally, if you’ve taken out your package within 24 hours, you may be able to cancel or amend your itinerary at no cost. If it’s been more than 24 hours, your hotel, airline or car rental company may impose a charge.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.