Book Holiday Homes in Winfield

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Featured Holiday Homes in Winfield

1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard!

1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard!

St Charles
With a stay at this vacation home, you'll be centrally located in St. Charles, a 2-minute drive from Ameristar Casino St. Charles and 6 minutes from Hollywood ...
1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard!
1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.

1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.

St. Charles
With a stay at this vacation home, you'll be centrally located in St. Charles, a 3-minute drive from Ameristar Casino St. Charles and 7 minutes from Hollywood ...
1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.
The  Cardinal Nest A Cozy Cottage on Historic Main Street; Pet Friendly

The Cardinal Nest A Cozy Cottage on Historic Main Street; Pet Friendly

St Charles mo
With a stay at this vacation home in St. Charles (St. Charles Historic District), you'll be a 1-minute drive from Ameristar Casino St. Charles and 6 minutes ...
The Cardinal Nest A Cozy Cottage on Historic Main Street; Pet Friendly
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Blair's House in St. Charles - Long Stays Welcome

Blair's House in St. Charles - Long Stays Welcome

Saint Charles
With a stay at this vacation home in St. Charles, you'll be within a 10-minute drive of Ameristar Casino St. Charles and Hollywood Casino Amphitheatre.
Blair's House in St. Charles - Long Stays Welcome
Blair's House - Game Room - Long Stays Welcome

Blair's House - Game Room - Long Stays Welcome

St. Peters
With a stay at this vacation home in St. Peters, you'll be within a 15-minute drive of Ameristar Casino St. Charles and Mid Rivers Mall.
Blair's House - Game Room - Long Stays Welcome
The St. Charles Guest House, lovely historic home, fun for families and groups

The St. Charles Guest House, lovely historic home, fun for families and groups

St Charles
With a stay at this vacation home, you'll be centrally located in St. Charles, a 3-minute drive from Ameristar Casino St. Charles and 7 minutes from Hollywood ...
The St. Charles Guest House, lovely historic home, fun for families and groups
Walk to St Charles Main St. Shops, Eateries & Bars! Bubble Tent!

Walk to St Charles Main St. Shops, Eateries & Bars! Bubble Tent!

Saint Charles
With a stay at this vacation home, you'll be centrally located in St. Charles, within a 5-minute drive of Ameristar Casino St. Charles and Historic Main ...
Walk to St Charles Main St. Shops, Eateries & Bars! Bubble Tent!
The Lewis & Clark Hangout

The Lewis & Clark Hangout

Saint Charles
The price is AU$625 per night from 16 Jan to 17 Jan
AU$625
includes taxes & fees
16 Jan - 17 Jan 2025
With a stay at this vacation home in St. Charles (St. Charles Historic District), you'll be a 3-minute drive from Ameristar Casino St. Charles and 6 minutes ...
The Lewis & Clark Hangout
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.

Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.

Saint Charles
With a stay at this vacation home in St. Charles, you'll be within a 10-minute drive of Ameristar Casino St. Charles and Katy Trail.
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.
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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.

Winfield Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Winfield vacation homes are the perfect way for you to wing it.

Holiday houses in Winfield let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Winfield in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Winfield adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Winfield with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Winfield vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Winfield Holiday Homes essential information

Accommodation
168 Holiday Homes
Lowest Price
AU$223
Highest Price
AU$625
Popular accommodation
1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard! , 1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo., The Cardinal Nest A Cozy Cottage on Historic Main Street; Pet Friendly, Blair's House in St. Charles - Long Stays Welcome, Blair's House - Game Room - Long Stays Welcome, The St. Charles Guest House, lovely historic home, fun for families and groups, Walk to St Charles Main St. Shops, Eateries & Bars! Bubble Tent!, The Lewis & Clark Hangout, Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.

Top trending hotels in Winfield

Spacious Riverfront Perch/Easy Access to St.Charles less than 1 Hr to St. Louis

Spacious Riverfront Perch/Easy Access to St.Charles less than 1 Hr to St. Louis

Winfield
When you stay at this cabin in Winfield, you'll be on the waterfront and steps from Mississippi River.
Spacious Riverfront Perch/Easy Access to St.Charles less than 1 Hr to St. Louis
Hollywood Casino & Hotel St. Louis

Hollywood Casino & Hotel St. Louis

3.5 out of 5
777 Casino Center Drive, Maryland Heights, MO
The price is AU$223 per night from 29 Dec to 30 Dec
AU$223
includes taxes & fees
29 Dec - 30 Dec
Located in Maryland Heights, Hollywood Casino & Hotel St. Louis is on a river, just a 3-minute walk from Hollywood Casino and a 4-minute drive from Hollywood ...
Hollywood Casino & Hotel St. Louis
Ameristar Casino Resort and Spa

Ameristar Casino Resort and Spa

4.5 out of 5
1 Ameristar Blvd, St. Charles, MO
Fully refundableReserve now, pay when you stay
The price is AU$343 per night from 24 Dec to 25 Dec
AU$343
includes taxes & fees
24 Dec - 25 Dec
A stay at Ameristar Casino Resort and Spa places you in the heart of St. Charles, steps from Ameristar Casino St. Charles and a 4-minute drive from Family ...
Ameristar Casino Resort and Spa
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The St. Charles Guest House, lovely historic home, fun for families and groups

The St. Charles Guest House, lovely historic home, fun for families and groups

St Charles
With a stay at this vacation home, you'll be centrally located in St. Charles, a 3-minute drive from Ameristar Casino St. Charles and 7 minutes from Hollywood ...
The St. Charles Guest House, lovely historic home, fun for families and groups
Don't see what you're looking for?
See all available properties in Winfield
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.