Winchester Holidays from £900

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to £750 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Packages with flights are ATOL protected

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was £1,042, price is now £900 per person
£900
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
London (LON) to St. Louis (STL)
8.8/10 Excellent! (1,061 reviews)
Location was great. Right in the arts district (everything in walking distance) and within 10 mins of downtown St. Louis. Staff were great and the roof top lounge was excellent.

Reviewed on 11 Jul 2026

The Cheshire

The Cheshire

4 out of 5
Price was £1,219, price is now £993 per person
£993
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
London (LON) to St. Louis (STL)
8.8/10 Excellent! (1,001 reviews)
Disappointed. Stayed on a road trip from Texas to Illinois. Pool played a big part in choosing the property but was unavailable during our one night stay because they were working on the roof. Would have been nice if they offered a discounted rate because of that. Breakfast was not “English style”, just a buffet. Bathroom in room was smelly. The adjacent bar/restaurant and tavern in the hotel were enjoyable.

Reviewed on 5 Jul 2026

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
Price was £1,220, price is now £1,040 per person
£1,040
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
London (LON) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
We had a great time at the hotel/casino. There is a lot of places to eat and drink on site. We will definitely be back to swim in the pool.

Reviewed on 10 Jul 2026

The Royal Sonesta Chase Park Plaza St. Louis

The Royal Sonesta Chase Park Plaza St. Louis

4.5 out of 5
Central West End
Price was £1,366, price is now £1,174 per person
£1,174
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
London (LON) to St. Louis (STL)
9/10 Wonderful! (1,011 reviews)
We enjoyed our stay!

Reviewed on 10 Jul 2026

Landing Furnished Apartments - Central West End

Landing Furnished Apartments - Central West End

3.5 out of 5
Central West End
Price was £1,138, price is now £990 per person
£990
per person
1 Oct - 6 Oct
found 1 day ago
Return flight included
London (LON) to St. Louis (STL)
7/10 Good! (4 reviews)
Parking was behind a large mechanical gate which did not always work. Could sometimes be noisy outside in the evening due to college clientele. Had to park on the street most of the time because of gate issues.

Reviewed on 6 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 22 Jul to 23 Jul
£51
22 Jul - 23 Jul
includes taxes & fees
8.4/10 Very good! (816 reviews)
"Great, helpful staff. Was clean but had large stain on carpet in our room."

Reviewed on 8 Jul 2026

Best Western Jacksonville Inn
Sleep Inn & Suites South Jacksonville

Sleep Inn & Suites South Jacksonville

3 out of 5
2401 Holliday Ln Jacksonville IL
Fully refundableReserve now, pay when you stay
The price is £74 per night from 26 Jul to 27 Jul
£74
26 Jul - 27 Jul
includes taxes & fees
9.4/10 Exceptional! (710 reviews)
"Very nice welcoming front desk staff. Pool and pool table, plus some casino style gaming (I think. We didn't do this). Typical chain hotel but nothing broken or worn out! Hot breakfast."

Reviewed on 6 Jul 2026

Sleep Inn & Suites South Jacksonville
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 18 Jul to 19 Jul
£54
18 Jul - 19 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
See all 73 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 £900. 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.