Winchester Holidays from £694

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    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Packages with flights are ATOL protected

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was £772, price is now £694 per person
£694
per person
3 Oct - 5 Oct
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
8.2/10 Very Good! (760 reviews)
I booked online and paid via the app. When I arrived on site they explained they had overbooked and had no rooms available. The staff was amazing and went above and beyond and secured a room at another location. Thank you to the staff for taking care of us.

Reviewed on 26 Jul 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was £1,022, price is now £774 per person
£774
per person
3 Oct - 5 Oct
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
9.2/10 Wonderful! (1,561 reviews)
Lots of restaurants in the area within walking distance.

Reviewed on 22 Aug 2025

CentralWestEnd-WashU-STL- Euphoria

CentralWestEnd-WashU-STL- Euphoria

2 out of 5
Central West End
Price was £1,348, price is now £1,175 per person
£1,175
per person
3 Oct - 5 Oct
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
10/10 Exceptional! (1 review)
DoubleTree by Hilton Hotel St. Louis - Chesterfield

DoubleTree by Hilton Hotel St. Louis - Chesterfield

4 out of 5
Price was £1,006, price is now £913 per person
£913
per person
7 Nov - 9 Nov
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
8.6/10 Excellent! (1,001 reviews)
Beautiful property, pleasant and responsive staff, delicious warm cookies! And convenient location near city hall and police department.

Reviewed on 27 Jul 2025

River City Casino & Hotel

River City Casino & Hotel

4 out of 5
Price was £831, price is now £756 per person
£756
per person
3 Oct - 5 Oct
found 1 day ago
Return direct flight included
London (LON) to St. Louis (STL)
9/10 Wonderful! (1,330 reviews)
The room was nice and clean. The bed was comfortable and there was a TV IN the bathroom mirror. That was pretty cool. Didn't use the shower but it was really nice. Check in was easy and the guy was pretty friendly. I would recommend this hotel.

Reviewed on 22 Aug 2025

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 21 Sept to 22 Sept
£66
21 Sept - 22 Sept
includes taxes & fees
9.2/10 Wonderful! (564 reviews)
"Nice place"

Reviewed on 18 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 18 Sept to 19 Sept
£47
18 Sept - 19 Sept
includes taxes & fees
8.2/10 Very Good! (595 reviews)
Nice
"Clean and quiet. Older hotel but very comfortable and accommodating."

Reviewed on 9 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 £63 per night from 18 Sept to 19 Sept
£63
18 Sept - 19 Sept
includes taxes & fees
8.4/10 Very Good! (698 reviews)
"Everything was so clean and staff was very helpful. We have found a new motel to stay in Jacksonville, Il.."

Reviewed on 17 Aug 2025

Best Western Jacksonville Inn
See all 44 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 £694. 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.