Winchester Holidays

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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 3.551.310 ₫ per night from 1 Sept to 2 Sept
3.551.310 ₫
4.188.024 ₫ total
1 Sept - 2 Sept
includes taxes & fees
8.4/10 Very Good! (3,975 reviews)
"The room was very nice. We used valet parking and it was quick and convenient."

Reviewed on 21 Aug 2025

Hyatt Regency St. Louis at The Arch
Renaissance St. Louis Airport Hotel

Renaissance St. Louis Airport Hotel

4 out of 5
9801 Natural Bridge Road, St. Louis, MO
Fully refundableReserve now, pay when you stay
The price is 3.209.332 ₫ per night from 4 Sept to 5 Sept
3.209.332 ₫
3.754.533 ₫ total
4 Sept - 5 Sept
includes taxes & fees
8.4/10 Very Good! (1,006 reviews)
"Easy checkin"

Reviewed on 23 Aug 2025

Renaissance St. Louis Airport Hotel
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 3.577.353 ₫ per night from 3 Sept to 4 Sept
3.577.353 ₫
4.182.964 ₫ total
3 Sept - 4 Sept
includes taxes & fees
9.4/10 Exceptional! (2,973 reviews)
"The staff was very nice & helpful. Have their own parking area that’s easy to get in. Our room was very clean & the breakfast was good. Walking distance to the arch & the stadium. We will be staying here again."

Reviewed on 23 Aug 2025

Drury Plaza Hotel St. Louis at the Arch
See all 1,772 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.

Popular places to visit

St. Louis Union Station

St. Louis Union Station

You can learn more about the history of St. Louis during your trip to a well-known site such as St. Louis Union Station. Experience the area's fascinating museums or attend a baseball game.

St. Louis Union Station
Gateway Arch showing a city, city views and skyline

Gateway Arch

Find out about the history of Gateway Arch, one of the top monuments in St. Louis. Experience the area's acclaimed art galleries or attend a baseball game.

Gateway Arch
St. Louis Zoo

St. Louis Zoo

Why not visit the animals who live at St. Louis Zoo during your holiday in St. Louis? Amble around the area's lush forest or attend a sporting event.

St. Louis Zoo

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.