Winchester Vacations from $258

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Your Winchester Vacation

When a fun city break is calling, answer it with a Winchester vacation package. The neighborhood of Maplewood, which is great for bars and pubs, gift and craft shops and dining, makes a terrific base for your adventures. There's plenty to include on your itinerary during your trip to Winchester, starting with top attractions such as Castlewood State Park and American Kennel Club Museum of the Dog. Your Winchester vacation is just clicks away. Explore hotels, flights and more on Expedia for a getaway that's tailored just for you.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Price was $370, price is now $258 per person
$258
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (763 reviews)
Great location! Super friendly staff!

Reviewed on Sep 27, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $473, price is now $271 per person
$271
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,581 reviews)
Nothing around within walking distance to eat except Mexican. The city of Wildwood needs to allow for commercial growth in the area. It's called urban sprawl. If not all the rich people in the area win. I won't be coming back

Reviewed on Sep 29, 2025

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

Angad Arts Hotel St. Louis, Tapestry Collection by Hilton

4 out of 5
Grand Center
Price was $427, price is now $302 per person
$302
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (1,005 reviews)
Great hotel will be returning

Reviewed on Sep 30, 2025

DoubleTree by Hilton St. Louis Forest Park

DoubleTree by Hilton St. Louis Forest Park

4 out of 5
Central West End
Price was $397, price is now $284 per person
$284
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (1,006 reviews)
We had requested a King room and received two Queen. That was a disappointment, but we made it work. Staff was great!

Reviewed on Sep 30, 2025

Hampton Inn By Hilton St Louis Airport

Hampton Inn By Hilton St Louis Airport

2.5 out of 5
Woodson Terrace
Price was $424, price is now $311 per person
$311
per person
Dec 15 - Dec 18
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.8/10 Excellent! (62 reviews)
The staff was very friendly and helpful. The rooms are amazing!

Reviewed on Sep 27, 2025

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Discover the most popular places to visit in Winchester

Busch Stadium

Busch Stadium

4.5/5(1,469 reviews)

Catch an event at Busch Stadium during your trip to St. Louis. Experience the area's acclaimed art scene or attend a baseball game.

Busch Stadium
St. Louis Union Station

St. Louis Union Station

4/5(615 reviews)

You can learn about the local history of St. Louis when you make a stop at a well-known site like St. Louis Union Station. Experience the area's acclaimed theater scene or attend a baseball game.

St. Louis Union Station
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

What to do in Winchester

St. Louis: Gateway Ghouls and Hauntings Walking Tour

St. Louis Ghost Tour: Sinister Sins & Shadows

$24
per adult
St. Louis Ghost Tour: Sinister Sins & Shadows
Lemp Haunted Neighborhood Walking Tour

Lemp Haunted Neighborhood Walking Tour

$27
per adult
84% of travellers recommend
Lemp Haunted Neighborhood Walking Tour
Step into the shadows and discover the haunting tales of our city's past.

St. Louis Ghosts: Gateway Ghouls and Hauntings

$32
per adult
100% of travellers recommend
St. Louis Ghosts: Gateway Ghouls and Hauntings
See all activities in Winchester

Winchester Hotel Deals

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
$134 nightly
The price is $157 total per night from Oct 15 to Oct 16
$157 total
Oct 15 - Oct 16
Total with taxes and fees
9.4/10 Exceptional! (3,099 reviews)
"It was a dream. East to get to the arch, beautiful property. Clean room."

Reviewed on Sep 27, 2025

Drury Plaza Hotel St. Louis at the Arch
Clayton Plaza Hotel & Extended Stay

Clayton Plaza Hotel & Extended Stay

3.5 out of 5
7750 Carondelet Avenue, St. Louis, MO
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $120 total per night from Oct 12 to Oct 13
$120 total
Oct 12 - Oct 13
Total with taxes and fees
8.8/10 Excellent! (2,970 reviews)
"Great staff and hotel!"

Reviewed on Sep 25, 2025

Clayton Plaza Hotel & Extended Stay
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
$125 nightly
The price is $147 total per night from Oct 2 to Oct 3
$147 total
Oct 2 - Oct 3
Total with taxes and fees
8.4/10 Very Good! (4,034 reviews)
"Great location and friendly staff!"

Reviewed on Sep 29, 2025

Hyatt Regency St. Louis at The Arch
See all 1,763 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.

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Frequently asked questions

How much does a Winchester vacation package cost?
You can snap up a vacation package to this top destination from $258 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?
You can usually find reduced prices and greater availability in January, October and December. Take a look at our cheap Winchester vacation packages and you could score some great off-season deals.
How many days is enough for Winchester?
Usually, a handful of days is enough to see the major attractions during your Winchester vacation. But if you prefer to have more time to unwind 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.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
If you're anything like us, you love discovering new places but don't love the big price tag that can come with it. That's why we've created Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Winchester vacation over 3, 6 or 12 months. There are also no hidden or late payment fees, so you can snap up great vacation packages with payment plans as soon as you see them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.