Winchester Trips (flight + hotel)

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    Better together
    Save up to P 3,118 when you book a flight and hotel together*
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    Find the right fit
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    Plan, book, and manage your trip all in one place

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 P7,763 per night from Jul 31 to Aug 1
P7,763
P9,155 total
Jul 31 - Aug 1
includes taxes & fees
8.4/10 Very Good! (3,814 reviews)
At the Arch
"The Hyatt Regency is a beautiful hotel with a beautiful view. Depending on what room you're in, you'll be able to see the Arch right out of your window. The rooms were clean, the staff was friendly, and the location downtown was great. My only real complaint is the price, but I guess you get what ..."

Reviewed on Jul 2, 2025

Hyatt Regency 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 P7,038 per night from Jul 15 to Jul 16
P7,038
P8,229 total
Jul 15 - Jul 16
includes taxes & fees
7/10 Good! (1,002 reviews)
"Very comfy and quiet"

Reviewed on Jun 25, 2025

The Arch Convention 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
Fully refundableReserve now, pay when you stay
The price is P7,875 per night from Jul 15 to Jul 16
P7,875
P9,208 total
Jul 15 - Jul 16
includes taxes & fees
9.4/10 Exceptional! (2,809 reviews)
"Friendly and attentive staff. Great amenities! Perfect location."

Reviewed on Jul 1, 2025

Drury Plaza Hotel St. Louis at the Arch
See all 1,779 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 Zoo featuring a park, a bridge and a lake or waterhole

St. Louis Zoo

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
Gateway Arch featuring central business district, modern architecture and skyline

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

America's Center Convention Complex

Learn about the events happening at America's Center Convention Complex during your trip to St. Louis. Experience the area's acclaimed theater scene and great live music.

America's Center Convention Complex

What to do in Winchester

St. Louis Arch Walking Tour and Entrance Ticket

St. Louis Arch Walking Tour and Entrance Ticket

P2,808
per adult
St. Louis Arch Walking Tour and Entrance Ticket
St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis: Gateway Ghouls and Hauntings Walking Tour

P1,348
per adult
St. Louis: Gateway Ghouls and Hauntings Walking Tour
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

P1,517
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
See all activities in Winchester

Frequently asked questions

How much does a Winchester vacation package cost?
You can snap up a vacation package to this top destination on Expedia. However, how much your vacation 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 vacation packages. Remember that school vacation 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 vacation. 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 vacation as a package?
Expedia vacation 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 personalized Winchester vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Winchester?
If you're planning a spur-of-the-moment Winchester vacation, 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 vacation 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.