Winchester Holidays from £883

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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.
La Quinta Inn & Suites by Wyndham Festus - St. Louis South

La Quinta Inn & Suites by Wyndham Festus - St. Louis South

3 out of 5
Price was £1,000, price is now £883 per person
£883
per person
8 Sept - 15 Sept
found 13 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
7.8/10 Good! (1,004 reviews)
Staff was great. Room was clean and quiet. Highly recommend

Reviewed on 8 Jul 2026

Tiny Houses of French Village

Tiny Houses of French Village

2.5 out of 5
Price was £1,467, price is now £1,231 per person
£1,231
per person
8 Sept - 15 Sept
found 13 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
10/10 Exceptional! (5 reviews)
Very nice place very clean well kept inside an out it's a nice little romantic getaway they have it set up so great its a must see sunset very relaxing

Reviewed on 22 Mar 2026

Best Western Plus Fenton

Best Western Plus Fenton

2.5 out of 5
Price was £1,079, price is now £943 per person
£943
per person
8 Sept - 15 Sept
found 13 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
9.2/10 Wonderful! (353 reviews)
Our room flooded and was told I could come downstairs and get a mop. Wow! They didn't offer to move us, change sheets discount off or anything just a oh well and here is a mop and bucket. Great job Best Western.

Reviewed on 6 Jul 2026

Extended Stay America Suites - St Louis - Fenton

Extended Stay America Suites - St Louis - Fenton

2.5 out of 5
Price was £992, price is now £886 per person
£886
per person
8 Sept - 15 Sept
found 13 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
5.8/10 (287 reviews)

River City Casino & Hotel

River City Casino & Hotel

4 out of 5
Price was £1,101, price is now £987 per person
£987
per person
8 Sept - 15 Sept
found 13 hours ago
Return direct flight included
London (LON) to St. Louis (STL)
9.2/10 Wonderful! (1,629 reviews)
Easy check in. Gorgeous rooms.

Reviewed on 7 Jul 2026

Winchester Essential Information

Language
English
Currency
U.S dollars
Population
1,500
Max Temp Winter
2ºC
Max Temp Summer
27ºC

Top hotels in Winchester

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 £51 per night from 14 Jul to 15 Jul
£51
14 Jul - 15 Jul
includes taxes & fees
8.4/10 Very good! (815 reviews)
"Great location, clean, pool and exercise room well maintained, staff was friendly and professional"

Reviewed on 7 Jul 2026

Best Western Jacksonville Inn
Jacksonville Inn & Suites

Jacksonville Inn & Suites

2 out of 5
1914 Southbrooke Rd Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is £54 per night from 9 Jul to 10 Jul
£54
9 Jul - 10 Jul
includes taxes & fees
7.8/10 Good! (31 reviews)
"Newly renovated rooms are nice. Nothing special but still nice."

Reviewed on 7 Jul 2026

Jacksonville 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 £49 per night from 16 Jul to 17 Jul
£49
16 Jul - 17 Jul
includes taxes & fees
8.2/10 Very good! (652 reviews)
"We did some volunteer work in Jacksonville that required 3 different times of staying several night each time. One several day stay we had 3 rooms. Each time we were all impressed! This hotel was amazing! The employees were so helpful and so kind. We saw them going above and beyond in the cleaning ..."

Reviewed on 4 Jul 2026

Super 8 by Wyndham Jacksonville
See all 72 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 £883. 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.

Explore a world of travel with Expedia

* 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.