Winfield Vacations from $294

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The Latest Winfield 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 $382, price is now $294 per person
$294
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.2/10 Very Good! (767 reviews)
Just a really nice hotel tucked away from everything, but still close to get whereevre you need to go!

Reviewed on Oct 26, 2025

The Wildwood Hotel

The Wildwood Hotel

3.5 out of 5
Save 100% on your flight
Price was $594, price is now $338 per person
$338
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.2/10 Wonderful! (1,591 reviews)
Fresh and seasonal waffles!

Reviewed on Oct 31, 2025

The Cheshire

The Cheshire

4 out of 5
Price was $526, price is now $395 per person
$395
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
8.6/10 Excellent! (1,008 reviews)
Everything was wonderful. The breakfast was awesome

Reviewed on Nov 1, 2025

The Knight Center at Washington University

The Knight Center at Washington University

2.5 out of 5
Price was $503, price is now $380 per person
$380
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.4/10 Exceptional! (416 reviews)
Great location and the room was perfect

Reviewed on Nov 2, 2025

WorldMark Lake of the Ozarks

WorldMark Lake of the Ozarks

3 out of 5
Price was $416, price is now $324 per person
$324
per person
Dec 12 - Dec 15
found 1 day ago
Roundtrip flight included
Dallas (DFW) to St. Louis (STL)
9.4/10 Exceptional! (402 reviews)
Great property! Your balcony view is directly on the water. This property offers a dock unused just for guests. I would bring your own raft or float to enjoy the water. The pools and hot tube area are nice, and offer grills for cooking in the pool area and another location. Check in was great except our room wasn’t ready until 5, the check in time was 4, however they made accommodations to us to offset the delay. It’s close to many fun things to do at the Lake of the Ozarks!! We will be back and will stay here again.

Reviewed on Aug 10, 2025

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Winfield Hotel Deals

Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
777 Casino Center Drive, Maryland Heights, MO
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $143 total per night from Nov 16 to Nov 17
$143 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (2,192 reviews)
Room had bad smell

Reviewed on Oct 23, 2025

Hollywood Casino & Hotel St. Louis
Hampton Inn St. Charles St. Peters

Hampton Inn St. Charles St. Peters

2.5 out of 5
3720 W Clay St, St. Charles, MO
Fully refundableReserve now, pay when you stay
$98 nightly
The price is $112 total per night from Nov 16 to Nov 17
$112 total
Nov 16 - Nov 17
Total with taxes and fees
7.8/10 Good! (1,010 reviews)
The breakfast menu was good but they need a bigger dining room because the hotel was full and they didn’t have enough tables to sit at. They also didn’t keep the food items full and they were constantly of different items. The front staff were very friendly and helpful especially Jennie. They also ...

Reviewed on Oct 27, 2025

Hampton Inn St. Charles St. Peters
Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
1 Ameristar Blvd, St. Charles, MO
$183 nightly
The price is $214 total per night from Nov 20 to Nov 21
$214 total
Nov 20 - Nov 21
Total with taxes and fees
8.4/10 Very Good! (1,011 reviews)
everyone was very friendly and helpful. Very enjoyable experience!

Reviewed on Oct 27, 2025

Ameristar Casino Resort and Spa
See all 501 properties in Winfield
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 Winfield Vacation Packages

Winfield Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Lambert-St. Louis Intl. Airport (STL)
Population
1,450

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Frequently asked questions

How much does a Winfield vacation package cost?
You can grab a vacation package to this top destination from $294 on Expedia. However, how much your vacation to Winfield costs will depend on factors like the season, hotel choice and length of stay.
What are the cheapest months to go to Winfield?
You can typically find reduced prices and greater availability in April, July and October. Check out our cheap Winfield vacation packages and you could get some great off-season discounts.
How many days is enough for Winfield?
The ideal length of your Winfield vacation depends on what you'd like to see. Typically, a handful of days to a week will give you time to hit all the main sights and explore some hidden spots along the way.
How to find the best Winfield package deals?
Use Expedia's filter tool to find some terrific Winfield package deals. When you begin your search, simply set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your trip for midweek, or look for Winfield package deals in the low season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as soon as possible.
Is it cheaper to book a Winfield vacation as a package?
You can enjoy significant savings on your Winfield break by booking a tailored vacation package. Click on the "Package" heading, then enter your destination and travel dates to view the best hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Winfield?
If you're considering a spur-of-the-moment Winfield getaway, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can land terrific deals on your flights and hotels by booking well in advance.
Does Expedia offer Book Now, Pay Later Winfield vacation packages?
Your Winfield break should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've partnered with online lender Affirm to offer you our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and split up the total cost over 3, 6 or 12 months. Plus, there aren't any hidden or late payment fees to worry about.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.