Winchester Vacations

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to ￥45,448 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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Find the Best Winchester Vacation Packages

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 ￥11,804 per night from Sep 7 to Sep 8
￥11,804
￥13,100 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (550 reviews)
"Tyler at the front desk was great, very friendly. Good breakfast"

Reviewed on Aug 10, 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 ￥8,163 per night from Aug 17 to Aug 18
￥8,163
￥9,304 total
Aug 17 - Aug 18
includes taxes & fees
8.2/10 Very Good! (593 reviews)
"Quiet clean convenient"

Reviewed on Aug 8, 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 ￥11,079 per night from Aug 11 to Aug 12
￥11,079
￥12,627 total
Aug 11 - Aug 12
includes taxes & fees
8.4/10 Very Good! (685 reviews)
"Very nice room. Was able to park right outside our room. Very close to lots of food options."

Reviewed on Jul 22, 2025

Best Western Jacksonville Inn
See all 43 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.

Frequently asked questions

How much does a Winchester vacation 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 vacation 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 vacation packages and you could get some great off-season discounts.
How many days is enough for Winchester?
The ideal length for your Winchester vacation 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 vacation package as soon as possible.
Is it cheaper to book a Winchester vacation as a package?
An Expedia vacation package could land you great savings when compared to booking hotels and flights individually. Better still, you can personalize 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 vacation 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 favorite 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 accommodations, 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 vacation. 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 personalized Winchester vacation package.

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