Book Holiday Homes in Winfield

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Featured Holiday Homes in Winfield

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 Hollywood Casino Amphitheatre.
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.
Gorgeous Lakefront Getaway - Innsbrook Chalet with Outdoor Spa!

Gorgeous Lakefront Getaway - Innsbrook Chalet with Outdoor Spa!

Innsbrook
With a stay at this vacation home in Wright City, you'll be on the waterfront, just a 1-minute walk from Cardinal Lake and 9 minutes by foot from Wren Lake.
Gorgeous Lakefront Getaway - Innsbrook Chalet with Outdoor Spa!
St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!

St Charles
The price is AU$436 per night from 1 May to 2 May
AU$436
includes taxes & fees
1 May - 2 May
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 ...
St. Charles 1860's Gem - Sleeps 6!
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Residence on the Roundabout

Residence on the Roundabout

St Charles
With a stay at this vacation home, you'll be centrally located in St. Charles, within a 10-minute drive of Ameristar Casino St. Charles and Hollywood Casino ...
Residence on the Roundabout
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome

☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome

St Peters
The price is AU$695 per night from 17 Apr to 18 Apr
AU$695
includes taxes & fees
17 Apr - 18 Apr
With a stay at this vacation home, you'll be centrally located in St. Peters, within a 15-minute drive of Mississippi River and Bowlero St. Peters.
☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome
Madison House 1 -Walk to Main St

Madison House 1 -Walk to Main St

Saint Charles
With a stay at this vacation home in St. Charles (St. Charles Historic District), you'll be a 4-minute drive from Ameristar Casino St. Charles and 6 minutes ...
Madison House 1 -Walk to Main St
Farmhouse 80 Acres Rec Room Peddle Boat Lake Fishing Nature Trl 2 ml to Grafton

Farmhouse 80 Acres Rec Room Peddle Boat Lake Fishing Nature Trl 2 ml to Grafton

Grafton
The price is AU$493 per night from 6 Apr to 7 Apr
AU$493
includes taxes & fees
6 Apr - 7 Apr
Located in Grafton, this vacation home is in a rural location, within a 10-minute drive of Grafton Ice Cream Company and Grafton Winery & Brewhaus.
Farmhouse 80 Acres Rec Room Peddle Boat Lake Fishing Nature Trl 2 ml to Grafton
Escape the city to quiet and picturesque Golden Eagle, IL..

Escape the city to quiet and picturesque Golden Eagle, IL..

Golden Eagle
This family-friendly vacation home is 3.3 mi (5.3 km) from Mississippi River and 16.8 mi (27 km) from Ameristar Casino St. Charles.
Escape the city to quiet and picturesque Golden Eagle, IL..
St. Charles Victorian Gem | Steps to Main Street

St. Charles Victorian Gem | Steps to Main Street

Saint Charles
The price is AU$1,147 per night from 17 Apr to 18 Apr
AU$1,147
includes taxes & fees
17 Apr - 18 Apr
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 ...
St. Charles Victorian Gem | Steps to Main Street
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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
208 Holiday Homes
Lowest Price
AU$203
Highest Price
AU$1,147
Popular accommodation
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown. , Gorgeous Lakefront Getaway - Innsbrook Chalet with Outdoor Spa!, St. Charles 1860's Gem - Sleeps 6!, Residence on the Roundabout, ☆BackYard BBQ Hidden Gem☆Perfect Location~Groups /Pets Welcome, Madison House 1 -Walk to Main St, Farmhouse 80 Acres Rec Room Peddle Boat Lake Fishing Nature Trl 2 ml to Grafton, Escape the city to quiet and picturesque Golden Eagle, IL.., St. Charles Victorian Gem | Steps to Main Street

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
With a stay at this cabin in Winfield, you'll be on the waterfront, just 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
Fully refundableReserve now, pay when you stay
The price is AU$225 per night from 16 Apr to 17 Apr
AU$225
includes taxes & fees
16 Apr - 17 Apr
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$341 per night from 13 Apr to 14 Apr
AU$341
includes taxes & fees
13 Apr - 14 Apr
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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Drury Plaza Hotel St. Louis St. Charles

Drury Plaza Hotel St. Louis St. Charles

3 out of 5
380 Mulholland Drive, St. Charles, MO
Fully refundableReserve now, pay when you stay
The price is AU$203 per night from 20 Apr to 21 Apr
AU$203
includes taxes & fees
20 Apr - 21 Apr
When you stay at Drury Plaza Hotel St. Louis St. Charles in St. Charles, you'll be in the business district, within a 5-minute drive of Ameristar Casino St. ...
Drury Plaza Hotel St. Louis St. Charles
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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.

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^Subject to availability and chosen travel dates.