Winchester Holidays

  • Plan, book, travel with confidence

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    Better together

    Save up to S$134 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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    Rest easy

    Plan, book, and manage your trip all in one place

Top hotels in Winchester

Comfort Inn & Suites Lawrence - University Area
Comfort Inn & Suites Lawrence - University Area
2.5 out of 5
151 Mcdonald Dr, Lawrence, KS
Fully refundableReserve now, pay when you stay
The price is S$131 per night from 21 Jul to 22 Jul
S$131
21 Jul - 22 Jul
includes taxes & fees
8.4/10 Very Good! (1,008 reviews)
"Nice room! Clean. Close to I-70"

Reviewed on 10 Jul, 2025

Comfort Inn & Suites Lawrence - University Area
DoubleTree by Hilton Hotel Lawrence
DoubleTree by Hilton Hotel Lawrence
4 out of 5
200 Mcdonald Dr, Lawrence, KS
Fully refundableReserve now, pay when you stay
The price is S$124 per night from 21 Jul to 22 Jul
S$124
21 Jul - 22 Jul
includes taxes & fees
8.4/10 Very Good! (1,002 reviews)
"Very enjoyable stay. Thanks for providing with toiletries I forgot"

Reviewed on 7 Jul, 2025

DoubleTree by Hilton Hotel Lawrence
Fairfield Inn & Suites Leavenworth
Fairfield Inn & Suites Leavenworth
2.5 out of 5
1101 North 4th Street, Leavenworth, KS
Fully refundableReserve now, pay when you stay
The price is S$191 per night from 13 Jul to 14 Jul
S$191
13 Jul - 14 Jul
includes taxes & fees
9/10 Wonderful! (440 reviews)
"very nice place to stay for a few days. better than some of the other hotels in the area."

Reviewed on 3 Jul, 2025

Fairfield Inn & Suites Leavenworth
See all 93 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 can pick up a holiday package to this top destination on Expedia. But how much your holiday to Winchester costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
If you'd like to book a cheap Winchester holiday package, consider visiting in January, February and November. You'll typically find better prices on accommodation and flights during these months --- perfect for budget-conscious travellers.
How many days is enough for Winchester?
The ideal duration for your Winchester holiday depends on what you'd like to do. Usually, a few days to a week will give you time to go to all the major attractions and explore some hidden spots along the way.
How to find the best Winchester package deals?
Bagging a cheap Winchester package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget, add some filters and see what's available. You can tweak your search by "Amenities," "Property type," "Popular locations" and more. Sort the results by "Price: low to high" to discover the most economical Winchester package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are usually lower.
Is it cheaper to book a Winchester holiday as a package?
You can enjoy significant savings on your next Winchester retreat by booking a personalised holiday package. Check the "Package" heading, then enter your travel dates and destination to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Winchester?
If you've got your Winchester holiday dates finalized, book as early as you can to snap up some terrific deals. With Expedia, you can generally reserve some flights up to one year in advance. Prefer spur-of-the-moment trips? Our last-minute deals are ideal for quick escapes.
How to plan a trip to Winchester?

  1. Choose your dates: The things you plan to do in Winchester and your preferred season will help you decide when to travel.
  2. Figure out your budget: Ensure you have enough money to cover everything from dining out and transportation to activities and airfares. Your accommodation will probably be the biggest expense during your trip to Winchester.
  3. Set the duration of your trip: Start by making a list of all the attractions you want to experience in Winchester. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your airfare and accommodation: Once you've nailed down your travel dates and duration, lock in the ideal Winchester holiday package for you.

* 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.