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.
The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $479, price is now $258 per person
$258
per person
Feb 14 - Feb 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.2/10 Wonderful! (1,600 reviews)
Breakfast great! Pool: hot tub being renovated.

Reviewed on Jan 12, 2026

White House at Grand Central

White House at Grand Central

4 out of 5
Grand Center
Save 100% on your flight
Price was $448, price is now $288 per person
$288
per person
Mar 20 - Mar 23
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (123 reviews)
Very clean and very friendly people

Reviewed on Nov 11, 2025

Hilton Garden Inn Chesterfield

Hilton Garden Inn Chesterfield

3 out of 5
Save 100% on your flight
Price was $378, price is now $274 per person
$274
per person
Feb 14 - Feb 16
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.2/10 Very Good! (779 reviews)
Staff was informative during check-in. Room was clean and the TV even had WELCOME with my name on it. Would stay here again.

Reviewed on Dec 22, 2025

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $462, price is now $346 per person
$346
per person
Mar 20 - Mar 23
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
9.4/10 Exceptional! (425 reviews)
The room was spotless, perfectly appointed, and the staff could not have been nicer. A perfect stay!

Reviewed on Jan 12, 2026

Marriott St. Louis West

Marriott St. Louis West

3.5 out of 5
Price was $431, price is now $328 per person
$328
per person
Mar 20 - Mar 23
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to St. Louis (STL)
8.6/10 Excellent! (1,000 reviews)
Wonderful, courteous staff who were genuinely friendly and helpful. Complimentary water, tea, and coffee. Clean, comfortable room. Highly recommend!

Reviewed on Jan 11, 2026

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Discover the most popular places to visit in Winchester

St. Louis Union Station

St. Louis Union Station

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 art scene or attend a baseball game.

St. Louis Union Station
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 showing a city, a skyscraper and skyline

Gateway Arch

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

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

$169
per adult
84% of travellers recommend
Best of St. Louis Small Group Tour w/ Arch & River Cruise
Step into the shadows and discover the haunting tales of our city's past.

St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour

$30
per adult
100% of travellers recommend
St Louis Ghost Tours: Sinister Sins & Shadows Ghost Tour
See all activities in Winchester

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
$125 nightly
The price is $147 total per night from Jan 16 to Jan 17
$147 total
Jan 16 - Jan 17
Total with taxes and fees
8.4/10 Very Good! (4,043 reviews)
Room was clean, excellent view!

Reviewed on Jan 13, 2026

Hyatt Regency St. Louis at The Arch
Hampton Inn St. Louis-Downtown (At the Gateway Arch)

Hampton Inn St. Louis-Downtown (At the Gateway Arch)

2.5 out of 5
333 Washington Ave St. Louis MO
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $114 total per night from Jan 21 to Jan 22
$114 total
Jan 21 - Jan 22
Total with taxes and fees
8.6/10 Excellent! (1,215 reviews)
No, the room wasn't spotless. One of the ottomans underneath the desk has some type of white crumbs or something on it. Other than that, the hospitality was nice.

Reviewed on Jan 11, 2026

Hampton Inn St. Louis-Downtown (At the Gateway Arch)
Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel

4 out of 5
421 N 8th St St. Louis MO
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $115 total per night from Jan 25 to Jan 26
$115 total
Jan 25 - Jan 26
Total with taxes and fees
8.6/10 Excellent! (1,190 reviews)
Wonderful stay

Reviewed on Jan 8, 2026

Magnolia Hotel St. Louis, a Tribute Portfolio Hotel
See all 1,834 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.

Find the Best Winchester Vacation Packages

Winchester Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
1,550

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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.