Winchester Holidays

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    Save up to S$134 when you book a flight and hotel together*
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Top hotels in Winchester

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 S$134 per night from 6 Apr to 7 Apr
S$134
includes taxes & fees
6 Apr - 7 Apr
9.2/10 Wonderful! (493 reviews)
"Great staff. Clean room."

Reviewed on 25 Mar,2025

Sleep Inn & Suites
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 S$114 per night from 27 Mar to 28 Mar
S$114
includes taxes & fees
27 Mar - 28 Mar
8.4/10 Very Good! (640 reviews)
"I liked everything about my stay except there was no body wash and being rushed out of the dining area"

Reviewed on 23 Mar,2025

Best Western Jacksonville Inn
Holiday Inn Express Hotel & Suites Jacksonville by IHG
Holiday Inn Express Hotel & Suites Jacksonville by IHG
2.5 out of 5
2501 Holliday Lane, Jacksonville, IL
Fully refundable
The price is S$102 per night from 6 Apr to 7 Apr
S$102
includes taxes & fees
6 Apr - 7 Apr
7.8/10 Good! (383 reviews)
"Great"

Reviewed on 22 Feb,2025

Holiday Inn Express Hotel & Suites Jacksonville by IHG
See all 40 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 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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.