Winfield Vacations from $376
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The Latest Winfield Vacation Packages
- Residence Inn by Marriott St Louis Downtown
Sep 24 - Sep 28Residence Inn by Marriott St Louis Downtown + Flight
Midtown4 nights3.0 star property7.8/10 - Good (1,002 reviews)"Check in tooks hours and went beyond 4pm making ua late for tickets we had, room smelled of old cigarettes, getting help with parking tickets was impossible and overall just a disappointment for a Marriott location."Reviewed July 31, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop - The Wildwood Hotel
Sep 6 - Sep 12The Wildwood Hotel + Flight
Wildwood6 nights3.5 star property9.2/10 - Wonderful (1,678 reviews)"The breakfast was really good."Reviewed August 5, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop$875$455found 1 day agoper traveler - Remodeled and Inviting Free EV
Sep 6 - Sep 12Remodeled and Inviting Free EV + Flight
Fenton6 nights2.0 star property10/10 - Exceptional (1 review)"The property was excellent, and the home was very warm and welcoming."Reviewed June 25, 2026Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop - Lodge Of Four Seasons Golf Resort, Marina & Spa
Sep 10 - Sep 16Lodge Of Four Seasons Golf Resort, Marina & Spa + Flight
Lake Ozark6 nights4.0 star property7.4/10 - Good (1,276 reviews)Roundtrip • Dallas (DFW) - St. Louis (STL)DAL - STL • Nonstop STL - DFW • 1 stop - The Cheshire
Sep 6 - Sep 12The Cheshire + Flight
Richmond Heights6 nights4.0 star property8.8/10 - Excellent (1,007 reviews)Roundtrip • Atlanta (ATL) - St. Louis (STL)ATL - STL • Nonstop STL - ATL • Nonstop
Winfield Hotel Deals
Holiday Inn Express & Suites St Peters by IHG
Holiday Inn Express & Suites St Peters by IHG"A great, easy place to stay!"
Drury Inn & Suites St. Louis St. Peters
Drury Inn & Suites St. Louis St. Peters"All staff were friendly and helpful. Providing dinner, drinks and breakfast were an excellent convenience."
Super 8 by Wyndham O'Fallon MO/St. Louis Area
Super 8 by Wyndham O'Fallon MO/St. Louis Area"Perfect"
Comfort Inn & Suites St. Louis - O'Fallon
Comfort Inn & Suites St. Louis - O'Fallon"Above and beyond service guest laundry available hotel front desk went extra mile by assisting with some paperwork I needed printing"
Fairfield Inn & Suites Wentzville
Fairfield Inn & Suites Wentzville"Helpful staff, nice room, nice breakfast selection. Right off the highway."
"Updated bathroom including safety measures,incredible mattress and much better breakfast than you expected for the money"
Hampton Inn St. Louis Wentzville
Hampton Inn St. Louis Wentzville
Hampton Inn St. Charles St. Peters
Hampton Inn St. Charles St. Peters"Property was under construction."
Frequently Asked Questions
How much does a Winfield vacation package cost?
You can grab a vacation package to this top destination from $376 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.