Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

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    Better together
    Save up to £335 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
    Packages with flights are ATOL protected

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
Stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful staff ...
9.2/10 Wonderful! (529 reviews)
"Very clean and friendly staff"

Reviewed on 21 Jun 2025

Sleep Inn & Suites
Best Western Jacksonville Inn
Best Western Jacksonville Inn
2.5 out of 5
1709 W Morton Ave, Jacksonville, IL
Stay at this hotel in Jacksonville. Enjoy free breakfast, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the clean rooms ...
8.4/10 Very Good! (668 reviews)
Home away from home
"The hotel is a little older, but very well maintained and clean. The staff was friendly and helpful. The breakfast was great and the beds were very comfy. We had the room with the jacuzzi tub and balcony overlooking the pool... very clean and spacious. We had a really nice time there!"

Reviewed on 24 Jun 2025

Best Western Jacksonville Inn
Baymont by Wyndham Jacksonville
Baymont by Wyndham Jacksonville
2.5 out of 5
1914 Southbrooke Road, Jacksonville, IL
Stay at this business-friendly hotel in Jacksonville. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Prairie Land Heritage Museam and ...
7/10 Good! (802 reviews)
"New."

Reviewed on 15 Jun 2025

Baymont by Wyndham Jacksonville
See all 42 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

Beach Holidays

Beach Holidays

Family Friendly Holidays

Family Friendly Holidays

Frequently asked questions

How much does a Winchester travel package cost?
From just . Yes, you read that correctly. Our Winchester travel packages are a simple way to make your budget last longer. Combine your favourite flights, hotels and rental car and get out and see this vibrant destination.
If I'm not able to travel, can I cancel my Winchester travel package?
It's hard to predict what tomorrow might bring, so it's good to know that you can change or cancel your Winchester travel package. If you made your booking in the last 24 hours, you may be entitled to a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal for more information.
How do I get a cheap travel package to Winchester?
Booking a Winchester travel package with Expedia is one of the best ways to save. We have over 550 air carriers and 1,000,000 hotels all over the world. With such a wonderful range to choose from, you'll have no difficulty putting together your ideal getaway.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Your bank balance shouldn't stop you from going on holiday, so Expedia has worked out a solution to help. Thanks to our partnership with online lender Klarna, it's easier than ever to book a fabulous getaway without hurting your hip pocket. Klarna offers flexible payment options during the checkout process that take the stress out of budgeting for your escape. Check out these flexible payment options:

  • Pay monthly holidays: Escape on that dream holiday sooner with Klarna's manageable monthly instalment plans. If paying bite-sized amounts each month sounds right for you, choose this option at checkout.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Consider this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: If paying a small percentage of your getaway (rather than all of it upfront) makes it easier to hit that "book now" button, opt for a low deposit holiday payment plan with Klarna.

What are the top hotels in Winchester?
Completely Renonvated Country Home With Llamas Just Outside The Windows is one of Winchester's leading properties. Check in to a room here and you'll be able to rest easy knowing you're in capable hands.
How far in advance should I book my Winchester holiday?
Travellers are normally able to compare international fares on Expedia within 12 months of departure. Booking at the last minute? With a little bit of luck, it's still possible to purchase an affordable ticket only weeks before your flight.
What does an Expedia Winchester travel package include?
Travel packages include flights, rental cars and hotels, but you can mix and match them to create your dream Winchester holiday. You can also add on fun stuff like tours and activities once you've made your booking. You're in control! When you combine your bookings with Expedia, you'll get access to discounts you won't find anywhere else.
What should I know before booking a Winchester travel package?
Tailor deals that match your budget with an Expedia package. Flights, hotels, rental cars --- we've got all of them. You'll save big dollars just by combining your bookings. Whether you're taking off on an adventure in the snow or sipping cocktails on a beach, your ideal getaway is only clicks away.
Can I choose my airline with a Winchester Expedia travel package?
Yes --- that's the beauty of an Expedia package. You can pick and choose your flights, hotels and more. We have access to more than 550 partner airlines globally, so you have loads of choice when creating your Winchester getaway.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.