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 €608
includes taxes & fees
7 Apr - 8 Apr
The cowboy Compound. 4-bedroom house in terrific Winfield with AC

Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton

Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton
Grafton
10.0 out of 10, Exceptional, (137 reviews)
"The property was amazing! The house gave me warm memories of my grandparents. Bed was extremely comfortable, we slept great. Definitely want to come back!"
United States
Susan M.
The price is €232
includes taxes & fees
11 Apr - 12 Apr
Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton

Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort
Grafton
10.0 out of 10, Exceptional, (58 reviews)
"Great place to stay, everything was what you expect. "
United States
Chris H.
The price is €260
includes taxes & fees
7 Apr - 8 Apr
Riverside Home - Modern meets comfort

Spacious 2 Bedroom Townhome

Spacious 2 Bedroom Townhome
Saint Charles
8.0 out of 10, Very good, (13 reviews)
"The stay here was amazing!! Live the little townhouse so much. Host was amazing!!"
United States
Tina W.
The price is €250
includes taxes & fees
7 Apr - 8 Apr
Spacious 2 Bedroom Townhome

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)
"Very clean and comfortable. Enjoyed our stay"
United States
Dana S.
The price is €420
includes taxes & fees
7 Apr - 8 Apr
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

The Original Custom House!

The Original Custom House!
St. Charles Historic District
9.8 out of 10, Exceptional, (36 reviews)
"The location is excellent. "
United States
McRay H.
The price is €306
includes taxes & fees
7 Apr - 8 Apr
The Original Custom House!

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, (36 reviews)
"Stay here for 3 weeks. Place was just as described. Would recommend. Thank you "
United States
Eddy
The price is €469
includes taxes & fees
9 Apr - 10 Apr
Charming open 4bd and screen-in porch! Sleeps 10!

Big Lake 'Livin A-Frame Chalet in Innsbrook Resort

Big Lake 'Livin A-Frame Chalet in Innsbrook Resort
Innsbrook
8.6 out of 10, Excellent, (10 reviews)
"We enjoyed the deck, hot tub, and paddle boat! Wonderful weekend!"
United States
Christine B.
Big Lake 'Livin A-Frame Chalet in Innsbrook Resort

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!
St. Charles Historic District
9.6 out of 10, Exceptional, (75 reviews)
"Great communication from host, cute house in an awesome location. Will definitely be staying again!"
United States
Sydney W.
The price is €194
includes taxes & fees
7 Apr - 8 Apr
Aunt Doodle’s House 8 blocks from Historic Main Street.. Convenient location!

Casa de Saint Charles

Casa de Saint Charles
Saint Charles
9.4 out of 10, Exceptional, (18 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 €341
includes taxes & fees
13 Apr - 14 Apr
Casa de Saint Charles

Serene Ivory*Fireplace*Fenced Yard* Dogs Welcome!

Serene Ivory*Fireplace*Fenced Yard* Dogs Welcome!
O'fallon
7.6 out of 10, Good, (8 reviews)
"Our family of six recently spent two weeks at this property and were thoroughly impressed. The home was exceptionally clean, quiet, and well-appointed, with ample linens and comfortable bedding for everyone. The soaker tub was an excellent feature that added to the overall comfort of our stay. The hosts were a pleasure to work with—professional, responsive, and always easy to reach. We would highly recommend this property to anyone seeking a well-maintained home and a seamless rental experience."
United States
J s.
The price is €459
includes taxes & fees
7 Apr - 8 Apr
Serene Ivory*Fireplace*Fenced Yard* Dogs Welcome!

Walk to St. Charles Entertainment

Walk to St. Charles Entertainment
Saint Charles
9.0 out of 10, Wonderful, (10 reviews)
"We really enjoyed our stay. The house was clean, spacious, and very accommodating. We stayed for a dance competition and the proximity to the convention center was unbeatable. "
United States
Chloe
The price is €255
includes taxes & fees
14 Apr - 15 Apr
Walk to St. Charles Entertainment

The Cozy Family Retreat

The Cozy Family Retreat
O'Fallon
8.4 out of 10, Very good, (23 reviews)
"Checkin was simple, house was clean and nice. Very roomy and accomdated 6 people very well. Easy to find and cute little neighborhood! Lots of amenities close by, shopping, food, etc. Thanks for a great stay!!!"
United States
Becky L.
The Cozy Family Retreat

Spacious 4BR Home for Families & Pets

Spacious 4BR Home for Families & Pets
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 €432
includes taxes & fees
27 Apr - 28 Apr
Spacious 4BR Home for Families & Pets

Spacious Townhome Retreat

Spacious Townhome Retreat
O Fallon
9.8 out of 10, Exceptional, (10 reviews)
"Great quiet neighborhood close to everything!"
United States
Jen D.
Spacious Townhome Retreat

Cottage on Historic Main Street- Low Cleaning fee

Cottage on Historic Main Street- Low Cleaning fee
St. Charles Historic District
10.0 out of 10, Exceptional, (12 reviews)
"A very quiet, clean and relaxing stay. "
United States
Dora S.
The price is €217
includes taxes & fees
9 Apr - 10 Apr
Cottage on Historic Main Street- Low Cleaning fee

Home Near Main Street-Covered Patio-Hot Tub!

Home Near Main Street-Covered Patio-Hot Tub!
Saint Charles
9.6 out of 10, Exceptional, (31 reviews)
"Great house and great location"
United States
Mike L.
Home Near Main Street-Covered Patio-Hot Tub!

Spring SALE,Cozy 2BR Chalet, Hot Tub 1.2 Acres!

Spring SALE,Cozy 2BR Chalet, Hot Tub 1.2 Acres!
Saint Charles
8.8 out of 10, Excellent, (3 reviews)
"We loved the location for our travel needs and we had everything we needed for a family of two adults and two dogs. "
United States
Leslie R.
Spring SALE,Cozy 2BR Chalet, Hot Tub 1.2 Acres!

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 Below Deck Suite

The Lewis & Clark Hangout

The Lewis & Clark Hangout
St. Charles Historic District
8.8 out of 10, Excellent, (23 reviews)
"Enjoyed our stay nice quiet neighborhood quaint house with plenty of off street parking"
United States
Jacqueline R.
The price is €406
includes taxes & fees
7 Apr - 8 Apr
The Lewis & Clark Hangout
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.
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
533
Accommodation
191 Holiday Homes
Lowest Price
€194
Highest Price
€608