Winchester Holidays

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Your Winchester Holiday

Book a Winchester holiday package and get set to experience the best of this lively city. Consider basing yourself in the neighbourhood of Maplewood, which is good for bars and pubs, gift and craft shops and dining. Searching for some sightseeing inspiration for your trip to Winchester? Castlewood State Park and American Kennel Club Museum of the Dog are two must-visit attractions here. Whoever you're travelling with and whatever the size of your budget, your dream Winchester holiday is just clicks away with Expedia.

Winchester Holiday

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

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 AU$250 per night from 31 July to 1 Aug
AU$250
31 July - 1 Aug
includes taxes & fees
8.4/10 Very Good! (3,815 reviews)
"We had the good fortune to be in a spacious corner room on the river side of the hotel. Looking out our window, we saw the majesty of the Arch, beauty of the park and river. The staff was very friendly and helpful."

Reviewed on 16 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
The price is AU$251 per night from 27 July to 28 July
AU$251
27 July - 28 July
includes taxes & fees
9.4/10 Exceptional! (2,849 reviews)
Great value!
"Such a great place! Great value!"

Reviewed on 16 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 AU$203 per night from 21 July to 22 July
AU$203
21 July - 22 July
includes taxes & fees
6.8/10 (1,016 reviews)
"A"

Reviewed on 18 Jul. 2025

The Arch Convention Hotel
See all 1,797 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

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Discover the most popular places to visit in Winchester

Busch Stadium

Busch Stadium

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's great live music or attend a baseball game.

Busch Stadium
Gateway Arch which includes skyline, a city and modern architecture

Gateway Arch

Visit the Museum of Westward Expansion, then ascend to the top of the tallest man-made monument in the US for breathtaking views of St. Louis.

Gateway Arch
Forest Park showing a pond, flowers and modern architecture

Forest Park

Nature, history and cultural institutions come together in one of the United States’ largest urban parks, which buzzes with St. Louis’ dynamic community spirit.

Forest Park

What to do in Winchester

St Louis: City Museum General Admission Ticket

St Louis: City Museum General Admission Ticket

AU$34
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

AU$49
per adult
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
Best of St. Louis Small Group Tour w/ Arch & River Cruise

Best of St. Louis Small Group Tour w/ Arch & River Cruise

AU$258
per adult
80% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
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.