Winchester Holidays

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Winchester Holiday

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
1,500
Max Temp Winter
2ºC
Max Temp Summer
27ºC

Our pick of the best Winchester Hotel Deals

Sleep Inn & Suites

Sleep Inn & Suites

2.5 out of 5
2401 Holliday Ln, Jacksonville, IL
Fully refundableReserve now, pay when you stay
The price is AU$136 per night from 7 Sept to 8 Sept
AU$136
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (552 reviews)
"Excellent"

Reviewed on 12 Aug. 2025

Sleep Inn & Suites
Super 8 by Wyndham Jacksonville

Super 8 by Wyndham Jacksonville

2 out of 5
1003 W Morton Ave, Jacksonville, IL
Fully refundableReserve now, pay when you stay
The price is AU$96 per night from 21 Aug to 22 Aug
AU$96
21 Aug - 22 Aug
includes taxes & fees
8.2/10 Very Good! (594 reviews)
Nice
"Clean and quiet. Older hotel but very comfortable and accommodating."

Reviewed on 9 Aug. 2025

Super 8 by Wyndham Jacksonville
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 AU$131 per night from 14 Aug to 15 Aug
AU$131
14 Aug - 15 Aug
includes taxes & fees
8.4/10 Very Good! (689 reviews)
"Everything was great except that the rooms did not have lotion. I asked the front desk and they said they didn’t provide that anymore. I’ve never been to a hotel that didn’t have any lotion. Other than that, this was a great stay!"

Reviewed on 8 Aug. 2025

Best Western Jacksonville Inn
See all 44 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 Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Winchester holiday package cost?
You'll find cheap prices on Expedia for your Winchester getaway. However, a range of factors like the length of stay, the season and your choice of hotel will determine how much your holiday to Winchester costs.
What are the cheapest months to go to Winchester?
You can generally find lower rates and greater availability in January, February and November. Browse our cheap Winchester holiday packages and you could get some great off-season discounts.
How many days is enough for Winchester?
The ideal length for your Winchester holiday depends on what you'd like to see. Typically, a few days to a week will give you plenty of time to tick off all the major attractions and discover some hidden spots along the way.
How to find the best Winchester package deals?
Use Expedia's handy filters to find some terrific Winchester package deals. When you start your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Winchester package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your holiday package as soon as possible.
Is it cheaper to book a Winchester holiday as a package?
An Expedia holiday package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalise your Winchester trip to fit your exact needs. Choose your preferred flight time, select the hotel type and add a rental car. Browse our great deals to see how much you can save.
When to book a holiday package to Winchester?
Secure fantastic discounts by reserving your flights in advance with Expedia. If being spontaneous is more your style, grab one of our last-minute deals for a spur-of-the-moment Winchester adventure.
How to plan a trip to Winchester?

  1. Choose when to go: Check your calendar and get your bags packed. Your favourite time of year and the activities available will also help you decide when to visit Winchester.
  2. Budget wisely: On top of the cost of your accommodation, you'll need to factor in other expenses. These include flights, transportation and food. Also, put aside a little extra for unexpected expenses that may arise during your trip to Winchester.
  3. Decide how long to go away for: Now that you're up to speed on Winchester, you can work out the ideal length of your holiday. Create a rough plan and give yourself enough time to get through everything on your must-do list.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a personalised Winchester holiday package.

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