Winchester Holidays

Book a Hotel + Flight or Car together to unlock savings

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    Better together

    Save up to NZ$616 when you book a flight and hotel together*
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    Find the right fit

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

Our pick of the best Winchester Hotel Deals

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 NZ$271 per night from 31 July to 1 Aug
NZ$271
31 July - 1 Aug
includes taxes & fees
8.4/10 Very Good! (3,828 reviews)
Location perfect!
"Location! Location! Location! Right across from the arch with restaurants in the hotel. Great stay & would visit again!"

Reviewed on 10 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 NZ$272 per night from 20 July to 21 July
NZ$272
20 July - 21 July
includes taxes & fees
9.4/10 Exceptional! (2,845 reviews)
"I loved how close this was to the St Louis arch National Park! My kids loved the pool and food. Love that there is a free breakfast but also a decent supper to be had. Wonderful stay. Hope to stay in a Drury the next trip we take."

Reviewed on 10 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 refundable
The price is NZ$220 per night from 14 July to 15 July
NZ$220
14 July - 15 July
includes taxes & fees
6.8/10 (1,008 reviews)
"The water was not working and turned off mid shower, was told be on in 10-15 minutes, still not on 45 minutes later"

Reviewed on 9 Jul. 2025

The Arch Convention Hotel
See all 1,802 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.

Discover the most popular places to visit in Winchester

Gateway Arch which includes skyline, a city and modern architecture

Gateway Arch

4.5/5(9 reviews)

Climb to the very top of America’s tallest man-made structure for sweeping views across the city of St. Louis and the surrounding countryside.

Gateway Arch
St. Louis Zoo

St. Louis Zoo

4/5(1 review)

In the middle of St. Louis, meet the exotic and endangered animals that live in meticulously recreated ecosystems from all over the world.

St. Louis Zoo
City Museum which includes a city as well as children

City Museum

3/5(1 review)

Leave all expectations at the door and let yourself be swept along by the weird, wacky and wildly exciting at this singular museum experience.

City Museum

What to do in Winchester

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

NZ$37
per adult
94% of travellers recommend
St Louis: City Museum General Admission Ticket
St. Louis Arch Walking Tour and Entrance Ticket

St. Louis Arch Walking Tour and Entrance Ticket

NZ$83
per adult
St. Louis Arch Walking Tour and Entrance Ticket
St Louis art museum

St. Louis Narrated Trolley Tour

NZ$50
per adult
92% of travellers recommend
St. Louis Narrated Trolley Tour
See all activities in Winchester

Frequently asked questions

How much does a Winchester holiday package cost?
You can snap up a holiday package to this top destination on Expedia. However, how much your holiday to Winchester costs will depend on your hotel choice, season and length of stay.
What are the cheapest months to go to Winchester?
Travel in the shoulder or low season and you're likely to find cheap Winchester holiday packages. Remember that school holiday periods and local events and festivals can impact prices, so do your research before booking.
How many days is enough for Winchester?
Generally, a handful of days is enough to check out the major attractions during your Winchester holiday. But if you want to have some time to kick back or go on day trips, think about extending your itinerary.
How to find the best Winchester package deals?
Begin your search for a Winchester package deal by entering your preferred travel dates and destination under our "Packages" tab. Then add a few filters, like "Property type" and "Popular locations," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with irresistible savings. If you don't find the perfect Winchester package deal straight away, just tweak your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winchester escape off to a flying start.
Is it cheaper to book a Winchester holiday as a package?
Expedia holiday packages are designed to help you keep more money in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component separately. And you'll still enjoy the flexibility to create a personalised Winchester holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Winchester?
If you're planning a spur-of-the-moment Winchester holiday, check out our last-minute deals that can be booked up to a week before you take off. Prefer not to wait until the last minute? You can find incredible deals on your hotels and flights by booking ahead.
How to plan a trip to Winchester?

  1. Pick the right time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to go to Winchester.
  2. Set your budget: Factor in expenses such as transportation, flights and meals when working out how much to save for your trip to Winchester. Then, pick a property that suits your budget, whether that's an affordable option or a more upscale getaway.
  3. Decide how long to go away for: Now that you're more familiar with Winchester, you can figure out the ideal length of your break. Put together a rough plan and allocate enough time to get through everything on your must-do list.
  4. Bundle your hotel and flights: Epic destination, check. Length of stay, check. All that's left now is to pick a Winchester holiday package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.