Winchester Holidays from £1,183

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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.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Manchester (MAN) to St. Louis (STL)
8.2/10 Very Good! (756 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
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Manchester (MAN) to St. Louis (STL)
9/10 Wonderful! (1,549 reviews)
For the price, this hotel was great. A cheap clean stopover in St. Louis. We were very happy to have cafes and restaurants within walking distance too! And parking was free.

Reviewed on 30 Jul 2025

Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Manchester (MAN) to St. Louis (STL)
8.4/10 Very Good! (1,000 reviews)
The hotel room was comfortable and well-kept - it’s a good spot for a weekend getaway or a night before flying out from the airport. Good mix of slots and tables.

Reviewed on 24 Jul 2025

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Manchester (MAN) to St. Louis (STL)
9.4/10 Exceptional! (337 reviews)
Property was well kept and great location

Reviewed on 29 Jul 2025

Moonrise Hotel

Moonrise Hotel

4 out of 5
Delmar Loop
per person
18 Oct - 24 Oct
found 1 day ago
Return flight included
Manchester (MAN) to St. Louis (STL)
9/10 Wonderful! (1,783 reviews)
Nice visual look and fun encased collectibles to look at.

Reviewed on 29 Jul 2025

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

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 £90 per night from 22 Aug to 23 Aug
£90
22 Aug - 23 Aug
includes taxes & fees
8.4/10 Very Good! (3,908 reviews)
"Parking was confusing but other than that this hotel was great!"

Reviewed on 28 Jul 2025

Hyatt Regency St. Louis at The Arch
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 £123 per night from 4 Aug to 5 Aug
£123
4 Aug - 5 Aug
includes taxes & fees
9.4/10 Exceptional! (2,902 reviews)
";)"

Reviewed on 28 Jul 2025

Drury Plaza Hotel St. Louis at the Arch
The Arch Convention Hotel

The Arch Convention Hotel

3.5 out of 5
811 N 9th Street, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is £95 per night from 10 Aug to 11 Aug
£95
10 Aug - 11 Aug
includes taxes & fees
6.8/10 (1,004 reviews)
Good
"It was overall a good stay. Staff was nice and helpful. Elevators sound like they need renovations. Room could be slightly cleaner but overall pretty solid. Ice machine weren’t working on my floor"

Reviewed on 26 Jul 2025

The Arch Convention Hotel
See all 1,795 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.
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Family Friendly Holidays

Popular places to visit

Gateway Arch showing a city, city views and skyline

Gateway Arch

5/5(16 reviews)

Enjoy 360-degree views and learn about the history of St. Louis at this world-famous landmark.

Gateway Arch

Six Flags St. Louis

5/5(1 review)

Bring the children to Six Flags St. Louis and have a fun-filled day at this theme park in St. Louis. While in this family-friendly area, you can savour the top-notch restaurants.

Six Flags St. Louis

Dome at America’s Center

5/5(4 reviews)

Catch an event at Dome at America’s Center during your trip to St. Louis. Experience the area's acclaimed art galleries and great live music.

Dome at America’s Center

What to do in Winchester

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

£17
per adult
96% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

£18
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
Pappy's Smokehouse

Private Gastronomy Tour (BBQ Joints & Breweries) in St. Louis

£96
per adult
Private Gastronomy Tour (BBQ Joints & Breweries) in St. Louis
See all activities in Winchester

Frequently asked questions

How much does a Winchester travel package cost?
From just £1,183. 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.