Winchester Holidays from £472

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Your Winchester Holiday

When a fun city break is calling, answer it with a Winchester holiday package. The neighbourhood of Maplewood, which is great for bars and pubs, gift and craft shops and dining, makes a terrific base for your adventures. There's plenty to include on your itinerary during your trip to Winchester, starting with top attractions such as Castlewood State Park and American Kennel Club Museum of the Dog. Your Winchester holiday is just clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored just for you.

Top Winchester Flight + Hotel Deals

Price found within the past 48 hours. Click for updated prices.
Crowne Plaza St. Louis Airport by IHG

Crowne Plaza St. Louis Airport by IHG

3.5 out of 5
Price was £568, price is now £472 per person
£472
per person
20 Dec - 25 Dec
found 1 day ago
Return direct flight included
Midland (MAF) to St. Louis (STL)
8/10 Very good! (1,004 reviews)

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Price was £805, price is now £489 per person
£489
per person
20 Dec - 25 Dec
found 1 day ago
Return direct flight included
Midland (MAF) to St. Louis (STL)
9.2/10 Wonderful! (1,677 reviews)

The Cheshire

The Cheshire

4 out of 5
Price was £779, price is now £604 per person
£604
per person
20 Dec - 25 Dec
found 1 day ago
Return direct flight included
Midland (MAF) to St. Louis (STL)
8.8/10 Excellent! (1,010 reviews)

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
Price was £765, price is now £598 per person
£598
per person
20 Dec - 25 Dec
found 1 day ago
Return direct flight included
Midland (MAF) to St. Louis (STL)
9/10 Wonderful! (2,047 reviews)

Marriott St. Louis Airport

Marriott St. Louis Airport

4 out of 5
Edmundson
Price was £696, price is now £577 per person
£577
per person
20 Dec - 25 Dec
found 1 day ago
Return direct flight included
Midland (MAF) to St. Louis (STL)
8/10 Very good! (1,002 reviews)

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
1,550
Max Temp Winter
4ºC
Max Temp Summer
32ºC

Top hotels in Winchester

Pear Tree Inn St. Louis Airport

Pear Tree Inn St. Louis Airport

2.5 out of 5
10810 Pear Tree Ln St. Ann MO
Fully refundableReserve now, pay when you stay
The price is £80 per night from 24 Nov to 25 Nov
£80
24 Nov - 25 Nov
includes taxes & fees
9.4/10 Exceptional! (3,361 reviews)
"There was only chips for evening meal. Didn’t have breakfast. Room was clean and staff were courteous"

Reviewed on 12 Nov 2026

Pear Tree Inn St. Louis Airport
Drury Plaza Hotel St. Louis at the Arch

Drury Plaza Hotel St. Louis at the Arch

3 out of 5
2 South 4th Street St. Louis MO
Fully refundableReserve now, pay when you stay
The price is £126 per night from 25 Nov to 26 Nov
£126
25 Nov - 26 Nov
includes taxes & fees
9.6/10 Exceptional! (3,832 reviews)
"Everything"

Reviewed on 12 Nov 2026

Drury Plaza Hotel St. Louis at the Arch
Hyatt Regency St. Louis at The Arch

Hyatt Regency St. Louis at The Arch

4 out of 5
315 Chestnut St St. Louis MO
Fully refundableReserve now, pay when you stay
The price is £95 per night from 26 Nov to 27 Nov
£95
26 Nov - 27 Nov
includes taxes & fees
8.6/10 Excellent! (4,378 reviews)
"Great experience and good location. View of the arch was awesome"

Reviewed on 12 Nov 2026

Hyatt Regency St. Louis at The Arch
See all 1,986 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

What to do in Winchester

Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

£19
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

£18
per adult
100% of travellers recommend
St. Louis Ghost Tour: Sinister Sins & Shadows
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

£20
per adult
100% of travellers recommend
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
See all activities in Winchester

Frequently asked questions

How much does a Winchester travel package cost?
From just £472. Yes, you read that right. Our Winchester travel packages are the easiest way to make your dollars go much further. Bundle your preferred hotels, flights and car rentals and get out and explore this top destination.
If I'm not able to travel, can I cancel my Winchester travel package?
If your travel plans in Winchester have been upended, it's comforting to know that you can cancel your booking. If you made your booking within the last 24 hours, you may be eligible for a refund. If your booking was made more than 24 hours ago, your airline, hotel or car rental company may charge a cancellation fee. For more details, visit our Customer Service Portal.
How do I get a cheap travel package to Winchester?
Our Winchester travel packages mean plenty of savings for the savvy globetrotter. For the best deal, simply combine your flights, hotels and extras (including activities) into an affordable package. But cheap prices are just the beginning of your next unforgettable adventure. Book with Expedia and and you'll have over 550 air carriers and 1,000,000 hotels globally to pick from. Whatever your style or budget, there's a travel package to suit you.
Does Expedia offer Book Now, Pay Later Winchester holidays?
Yes. Expedia has joined forces with online lender Klarna to help you conveniently pay for your holiday in manageable instalments. Simply choose the payment plan that works for you during the checkout process and take away the stress of budgeting for your next trip. Don't forget to bundle your flights, car hire and hotel with Expedia to get the biggest bang for your travel buck. Check out our flexible payment options below:

  • Pay monthly holidays: Klarna offers easy monthly payment plans that suit all types of budgets, so you can jet away on that well-deserved holiday now.
  • Pay in instalments holidays: Like the idea of paying down your holiday in multiple transactions? Then select this Book Now, Pay Later option from Klarna.
  • Low deposit holidays: If paying a small percentage of your trip (rather than the full total upfront) makes it easier to click that "book now" button, consider a low deposit holiday payment plan from Klarna.

Where should I stay in Winchester?
If you'll be checking out American Kennel Club Museum of the Dog, forget about commuting and find a place to stay close by. It's one of the best attractions in this area.
What are the top hotels in Winchester?
If it's comfort and convenience you want, you won't beat Spacious 4 Bedroom Home. Spend your nights relaxing here and your days checking out Winchester's popular attractions.
How far in advance should I book my Winchester holiday?
While not all air carriers advertise tickets early, customers are usually able to look up international airfares on Expedia up to a year in advance. This is the time when you can score some fantastic bargains. If you're booking at the last minute, you may still be in luck. Sometimes the cheapest prices emerge a few weeks prior to departure.
What does an Expedia Winchester travel package include?
Rental cars, hotels and flights, or any combination of the three — it's totally up to you. Whether you're visiting Winchester with the family or travelling by yourself, there's a package to suit every style and budget. Once you've made your booking, why not add on a couple of activities?
What should I know before booking a Winchester travel package?
An Expedia travel package can be customized for your budget and is a simple way to stretch your dollars further. How little or much you include is up to you. Rental cars, hotels and flights — mix and match whatever combination suits your plans.
Can I choose my airline with a Winchester Expedia travel package?
Yes, you're in charge. We offer more than 550 partner airlines throughout the world, so you can customize your Winchester adventure according to your travel needs.

* 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.