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

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 £66 per night from 7 Sept to 8 Sept
£66
7 Sept - 8 Sept
includes taxes & fees
9.2/10 Wonderful! (547 reviews)
Budget friendly, clean room
"Very nice stay. Walls a little thin but everything you could want/expect in a hotel room is provided. Clean and nicely arranged. They make it easy to get in and out quickly but don’t skip any amenities."

Reviewed on 1 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 £47 per night from 17 Aug to 18 Aug
£47
17 Aug - 18 Aug
includes taxes & fees
8.2/10 Very Good! (593 reviews)
"Quiet clean convenient"

Reviewed on 8 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 £64 per night from 10 Aug to 11 Aug
£64
10 Aug - 11 Aug
includes taxes & fees
8.4/10 Very Good! (683 reviews)
"Very nice room. Was able to park right outside our room. Very close to lots of food options."

Reviewed on 22 Jul 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.
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.