Winchester Vacations

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Find the Best Winchester Vacation Packages

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 ₩190,048 per night from Jul 31 to Aug 1
₩190,048
₩224,122 total
Jul 31 - Aug 1
includes taxes & fees
8.4/10 Very Good! (3,845 reviews)
"Close to the Gateway Arch for the July 4th fireworks"

Reviewed on Jul 13, 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 ₩192,789 per night from Jul 20 to Jul 21
₩192,789
₩225,427 total
Jul 20 - Jul 21
includes taxes & fees
9.4/10 Exceptional! (2,849 reviews)
"Excellent all around"

Reviewed on Jul 12, 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 ₩155,688 per night from Jul 14 to Jul 15
₩155,688
₩182,044 total
Jul 14 - Jul 15
includes taxes & fees
6.8/10 (1,012 reviews)
"Сам отель и комната были довольно комфортные. Обслуживающий персоонал работал отлично. Сначала мне дали комнату на 5 этаже, но там было жарко. Тогда мне поменяли комнату на 4 этаж, где было прохладнее. Единственное, что мне не понравилось - старые слабые кодиционеры."

Reviewed on Jul 11, 2025

The Arch Convention Hotel
See all 1,805 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 showing a city, a skyscraper and skyline

Gateway Arch

4.5/5(2,511 reviews)

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

Gateway Arch
St. Louis Zoo

St. Louis Zoo

4.5/5(1,212 reviews)

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
Seeing one of the largest hotels decked out in Rainbow lights in St. Louis is pretty awesome! Lots of food and drink options at this hotel & casino! #LifeAtExpedia

Horseshoe St. Louis Casino

4/5(14 reviews)

Why not roll the dice with a visit to Horseshoe St. Louis Casino during your time in St. Louis? Experience the area's fascinating museums or attend a baseball game.

Horseshoe St. Louis Casino

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.