Holiday Homes in Winfield

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winfield holiday homes

The cowboy Compound. 4-bedroom house in terrific Winfield with AC

The cowboy Compound. 4-bedroom house in terrific Winfield with AC
Winfield
The price is AU$953
includes taxes & fees
16 Feb - 17 Feb
The cowboy Compound. 4-bedroom house in terrific Winfield with AC

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
10.0 out of 10, Exceptional, (132 reviews)
"We loved our stay here!! It offers so much and is a perfect location! The owners are great and answered every question and responded instantly! Highly recommend and we will for sure be back for our next trip to Grafton! "
United States
JD B.
The price is AU$325
includes taxes & fees
20 Feb - 21 Feb
Farmhouse 80 Acres Rec Room Peddle Boat Lake Fishing Nature Trl 2 ml to Grafton

Charming 2-bedroom townhome with a cozy fireplace in the heart of Grafton

Charming 2-bedroom townhome with a cozy fireplace in the heart of Grafton
Grafton
9.8 out of 10, Exceptional, (10 reviews)
"Great Stay. Clean, excellent accomodations."
United States
Brad H.
The price is AU$538
includes taxes & fees
16 Feb - 17 Feb
Charming 2-bedroom townhome with a cozy fireplace in the heart of Grafton

The Below Deck Suite

The Below Deck Suite
Saint Charles
9.0 out of 10, Wonderful, (2 reviews)
"Overall good place for a family. The neighborhood is quiet and there is a good amount of space. Easy to find and to get places. You will hear the people upstairs and one bed was very squeaky. It was very clean and the couches are very comfy. "
United States
Amy B.
The price is AU$441
includes taxes & fees
24 Feb - 25 Feb
The Below Deck Suite

Charming open 4bd and screen-in porch! Sleeps 10!

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
9.2 out of 10, Wonderful, (34 reviews)
"Stay here for 3 weeks. Place was just as described. Would recommend. Thank you "
United States
Eddy
The price is AU$698
includes taxes & fees
16 Feb - 17 Feb
Charming open 4bd and screen-in porch! Sleeps 10!

Casa de Saint Charles

Casa de Saint Charles
Saint Charles
9.2 out of 10, Wonderful, (17 reviews)
"The home was perfect for our multi-family gathering. There was lots of room for everyone and the location was great for our needs."
United States
Karla Z.
The price is AU$455
includes taxes & fees
16 Feb - 17 Feb
Casa de Saint Charles

Spacious 2 bed Townhome by StayLage

Spacious 2 bed Townhome by StayLage
Saint Charles
9.0 out of 10, Wonderful, (10 reviews)
"Great location, clean, and management was informative and reacted to any needs quickly. Would recommend to anyone."
United States
Nathan D.
The price is AU$437
includes taxes & fees
16 Feb - 17 Feb
Spacious 2 bed Townhome by StayLage

The Cozy Family Retreat

The Cozy Family Retreat
O'Fallon
8.4 out of 10, Very good, (23 reviews)
"Great hosts. Place was comfortable. "
United States
Vicky W.
The price is AU$421
includes taxes & fees
26 Feb - 27 Feb
The Cozy Family Retreat

Beautiful+Spacious+FencedYard🐕Grill+Patio+Walk2Park+27MileBikeTrail🚴‍♀️

Beautiful+Spacious+FencedYard🐕Grill+Patio+Walk2Park+27MileBikeTrail🚴‍♀️
St. Peters
10.0 out of 10, Exceptional, (23 reviews)
"Clean and close to everything you would want for a stay ."
United States
Judy H.
The price is AU$561
includes taxes & fees
23 Feb - 24 Feb
Beautiful+Spacious+FencedYard🐕Grill+Patio+Walk2Park+27MileBikeTrail🚴‍♀️

Quaint and Cozy Hamlet

Quaint and Cozy Hamlet
O'Fallon
9.6 out of 10, Exceptional, (14 reviews)
"Wonderful for families! Host had many little welcoming extras."
United States
Stephanie W.
The price is AU$583
includes taxes & fees
18 Mar - 19 Mar
Quaint and Cozy Hamlet

Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort
Grafton
10.0 out of 10, Exceptional, (57 reviews)
"Wife and I both loved the outside seating in front and back. Very nice place to stay"
United States
David C.
The price is AU$459
includes taxes & fees
16 Feb - 17 Feb
Riverside Home - Modern meets comfort

Spacious 2 Bedroom Townhome by StayLage

Spacious 2 Bedroom Townhome by StayLage
Saint Charles
7.8 out of 10, Good, (12 reviews)
"Perfect size"
United States
Barbie D.
The price is AU$426
includes taxes & fees
16 Feb - 17 Feb
Spacious 2 Bedroom Townhome by StayLage

Madison House 1 -Walk to Main St

Madison House 1 -Walk to Main St
St. Charles Historic District
8.6 out of 10, Excellent, (17 reviews)
"The house was clean and well stocked, location was great, and plenty of street parking. "
United States
Brad K.
The price is AU$360
includes taxes & fees
22 Feb - 23 Feb
Madison House 1 -Walk to Main St

St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (140 reviews)
"Another great stay! "
United States
Kate G.
The price is AU$371
includes taxes & fees
16 Feb - 17 Feb
St. Charles 1860's Gem - Sleeps 6!

The Original Custom House!

The Original Custom House!
St. Charles Historic District
9.8 out of 10, Exceptional, (36 reviews)
"Location is perfect. Clean and exactly what we were looking for in a weekend get away. The common areas (living room and kitchen) are on the smaller side if you are wanting a place to gather but we were out and about most of the time so it was perfect for us. "
United States
Amanda G.
The price is AU$523
includes taxes & fees
16 Feb - 17 Feb
The Original Custom House!

4 Bedroom Wentzville Home by StayLage

4 Bedroom Wentzville Home by StayLage
Wentzville
9.8 out of 10, Exceptional, (6 reviews)
"Amazing for attending the fireworks festivals nearby. Great shops walking distance for coffee and food"
United States
Tom K.
The price is AU$767
includes taxes & fees
22 Feb - 23 Feb
4 Bedroom Wentzville Home by StayLage

New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!
St. Charles Historic District
9.6 out of 10, Exceptional, (68 reviews)
"Spacious, clean and well stocked house. Very comfortable and located in a very nice neighborhood. "
United States
Mary Y.
The price is AU$679
includes taxes & fees
16 Feb - 17 Feb
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

Stunning 1890's Home - Sleeps 8!

Stunning 1890's Home - Sleeps 8!
St. Charles Historic District
10.0 out of 10, Exceptional, (106 reviews)
"Beautiful property within walking distance to Main St."
United States
KEITH M.
The price is AU$510
includes taxes & fees
16 Feb - 17 Feb
Stunning 1890's Home - Sleeps 8!

Historic 4‑BR Farmhouse • Steps to Main Street

Historic 4‑BR Farmhouse • Steps to Main Street
St. Charles Historic District
10.0 out of 10, Exceptional, (22 reviews)
"The house was perfect for our stay. "
United States
Susan F.
The price is AU$849
includes taxes & fees
10 Mar - 11 Mar
Historic 4‑BR Farmhouse • Steps to Main Street

Home Near Main Street-Covered Patio-Hot Tub!

Home Near Main Street-Covered Patio-Hot Tub!
Saint Charles
9.8 out of 10, Exceptional, (29 reviews)
"We absolutely loved our stay in St. Charles. This property was perfect for our family with plenty of space and very clean! Great communication and responsiveness from owner. We would definitely book this property again in the future. "
United States
Danielle T.
The price is AU$698
includes taxes & fees
16 Feb - 17 Feb
Home Near Main Street-Covered Patio-Hot Tub!
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

Top Winfield Hotel Reviews

Find out more about Winfield

Winfield Holiday Homes information

Number of reviews
749
Accommodation
191 Holiday Homes
Lowest Price
AU$325
Highest Price
AU$953