Winfield Holiday Rentals

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Check prices for these dates

Tonight
24 Dec - 25 Dec
Tomorrow
25 Dec - 26 Dec
This weekend
26 Dec - 28 Dec
Next weekend
2 Jan - 4 Jan

Our top choices for Winfield holiday rentals

Bar (on property)
The Harris Overlook by Innsbrook Vacations!

The Harris Overlook by Innsbrook Vacations!

The Harris Overlook by Innsbrook Vacations!
Innsbrook
9.6 out of 10, Exceptional, (18)
"Great location and property within close distance of all Innsbrook has to offer. Would stay again. "
United States
Kristina U.
The price is HK$543
HK$1,718 total
includes taxes & fees
25 Dec - 26 Dec
The Harris Overlook by Innsbrook Vacations!
Bar (on property)
The Geneva Studio by Innsbrook Vacations!

The Geneva Studio by Innsbrook Vacations!

The Geneva Studio by Innsbrook Vacations!
Innsbrook
10.0 out of 10, Exceptional, (1)
"The property is well kept and clean. The condo was clean and well furnished. "
United States
John S.
The price is HK$544
HK$1,719 total
includes taxes & fees
25 Dec - 26 Dec
The Geneva Studio by Innsbrook Vacations!
TV
6th street 101 - Walk to Main St

6th street 101 - Walk to Main St

6th street 101 - Walk to Main St
St. Charles Historic District
10.0 out of 10, Exceptional, (1)
The price is HK$770
HK$2,212 total
includes taxes & fees
28 Dec - 29 Dec
6th street 101 - Walk to Main St
Bar (on property)
Lake Aspen Overlook by Innsbrook Vacations!

Lake Aspen Overlook by Innsbrook Vacations!

Lake Aspen Overlook by Innsbrook Vacations!
Innsbrook
9.8 out of 10, Exceptional, (23)
"Everything was extremely clean. We couldn’t have asked for a more quiet and relaxing stay. "
United States
Brian L.
The price is HK$543
HK$1,718 total
includes taxes & fees
25 Dec - 26 Dec
Lake Aspen Overlook by Innsbrook Vacations!
Bar (on property)
Serene Seebach Sights by Innsbrook Vacations!

Serene Seebach Sights by Innsbrook Vacations!

Serene Seebach Sights by Innsbrook Vacations!
Innsbrook
9.4 out of 10, Exceptional, (10)
"Great clubhouse, plenty of wildlife roaming grounds, and friendly atmosphere."
United States
tony
Serene Seebach Sights by Innsbrook Vacations!
Fridge, microwave, oven, stovetop
The Hidden Gem - 2BR Basement Apartment on 7 Acres

The Hidden Gem - 2BR Basement Apartment on 7 Acres

The Hidden Gem - 2BR Basement Apartment on 7 Acres
Moscow Mills
10.0 out of 10, Exceptional, (12)
"Another incredible stay at the Hidden Gem. The apartment was very clean and had everything we could ever need for the Labor Day weekend. Looking forward to staying again when the family reunion gets back to Troy, MO"
United States
Doug D.
The price is HK$856
HK$1,937 total
includes taxes & fees
29 Dec - 30 Dec
The Hidden Gem - 2BR Basement Apartment on 7 Acres
2 bedrooms, desk, iron/ironing board, free WiFi
Spacious Townhome Retreat by StayLage

Spacious Townhome Retreat by StayLage

Spacious Townhome Retreat by StayLage
O Fallon
9.8 out of 10, Exceptional, (9)
"This was the perfect place for us and our adult daughter while we were in town for our sons wedding."
United States
Tanya h.
The price is HK$1,386
HK$3,498 total
includes taxes & fees
3 Jan - 4 Jan 2026
Spacious Townhome Retreat by StayLage
Bar (on property)
Lake Aspen Hideaway by Innsbrook Vacations!

Lake Aspen Hideaway by Innsbrook Vacations!

Lake Aspen Hideaway by Innsbrook Vacations!
Wright City
9.8 out of 10, Exceptional, (21)
"Check-in was easy and property was clean. Great place to stay!"
United States
Casey A.
The price is HK$544
HK$1,711 total
includes taxes & fees
11 Jan - 12 Jan 2026
Lake Aspen Hideaway by Innsbrook Vacations!
TV
1st Capitol Mansion - Suite 401

1st Capitol Mansion - Suite 401

1st Capitol Mansion - Suite 401
St. Charles Historic District
8.4 out of 10, Very good, (7)
"Nice property and a great location to all the shops and restaurants that St. Charles has to offer. The place was clean and nicely updated. Will definitely stay here again!"
United States
Emily L.
The price is HK$770
HK$1,951 total
includes taxes & fees
6 Jan - 7 Jan 2026
1st Capitol Mansion - Suite 401
TV
Historic 5th Street House - Fully Rehabbed # 2

Historic 5th Street House - Fully Rehabbed # 2

Historic 5th Street House - Fully Rehabbed # 2
St. Charles Historic District
8.8 out of 10, Excellent, (11)
"Wonderful place to stay would definitely recommend "
United States
Steven S.
The price is HK$770
HK$1,920 total
includes taxes & fees
19 Jan - 20 Jan 2026
Historic 5th Street House - Fully Rehabbed # 2
Games room
Madison House 1 -Walk to Main St

Madison House 1 -Walk to Main St

Madison House 1 -Walk to Main St
St. Charles Historic District
8.4 out of 10, Very good, (15)
"The house was clean and well stocked, location was great, and plenty of street parking. "
United States
Brad K.
The price is HK$770
HK$1,982 total
includes taxes & fees
4 Jan - 5 Jan 2026
Madison House 1 -Walk to Main St
3 bedrooms, iron/ironing board, WiFi, bed sheets
The Below Deck Suite

The Below Deck Suite

The Below Deck Suite
Saint Charles
9.0 out of 10, Wonderful, (2)
"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 HK$1,221
HK$2,372 total
includes taxes & fees
1 Jan - 2 Jan 2026
The Below Deck Suite
Fridge, microwave, oven, stovetop
St. Peters Private Basement Guesthouse: Farm Views - Visit Family & Friends

St. Peters Private Basement Guesthouse: Farm Views - Visit Family & Friends

St. Peters Private Basement Guesthouse: Farm Views - Visit Family & Friends
St. Peters
9.8 out of 10, Exceptional, (7)
"Perfectly appointed property from amenities inside to lighted walk-ways outside. Excellent location (for us) to family, friends, and the highway! Very serene area and felt totally safe at all times - even walking to the car at night by myself. "
United States
Lisa & Fred W.
The price is HK$739
HK$2,185 total
includes taxes & fees
12 Jan - 13 Jan 2026
St. Peters Private Basement Guesthouse: Farm Views - Visit Family & Friends
Interior
Quaint and Cozy Hamlet

Quaint and Cozy Hamlet

Quaint and Cozy Hamlet
O'Fallon
9.4 out of 10, Exceptional, (13)
"Overall great time- communication was wonderful with Kevin, neighborhood was quiet, perfect for our stay. The house wasn’t as clean as I’d expect but besides that, great stay!"
United States
Madison A.
The price is HK$786
HK$2,713 total
includes taxes & fees
7 Jan - 8 Jan 2026
Quaint and Cozy Hamlet
Dining
Cozy 3 Bedroom/ Family Comfort & Convenient Location

Cozy 3 Bedroom/ Family Comfort & Convenient Location

Cozy 3 Bedroom/ Family Comfort & Convenient Location
2.0 star property
Wentzville
10.0 out of 10, Exceptional, (1)
"We had a wonderful stay! The home was very clean, check-in was super easy, and it was the perfect place for our family. Everything was exactly as described and we felt comfortable the entire time. Would definitely stay here again!"
United States
Tricia W.
The price is HK$934
HK$2,404 total
includes taxes & fees
30 Dec - 31 Dec
Cozy 3 Bedroom/ Family Comfort & Convenient Location
Bar (on property)
Lake Aspen Landing by Innsbrook Vacations!

Lake Aspen Landing by Innsbrook Vacations!

Lake Aspen Landing by Innsbrook Vacations!
Innsbrook
9.2 out of 10, Wonderful, (12)
"This was a great spot for me and my granddaughter to stay. Within walking distance to the beach. It was clean, quiet and even during the rain there were puzzles and some games available to play. Nicely decorated. "
United States
Jaime S.
The price is HK$543
HK$1,718 total
includes taxes & fees
25 Dec - 26 Dec
Lake Aspen Landing by Innsbrook Vacations!
Marina
Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort
Grafton
10.0 out of 10, Exceptional, (57)
"Wife and I both loved the outside seating in front and back. Very nice place to stay"
United States
David C.
The price is HK$972
HK$2,580 total
includes taxes & fees
19 Jan - 20 Jan 2026
Riverside Home - Modern meets comfort
Smart TV
Prime Loft of Main Street

Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (101)
"The loft was very nice, very clean, well appointed, and in a perfect location. I highly recommend this property!"
United States
Mary ann S.
The price is HK$763
HK$1,771 total
includes taxes & fees
4 Jan - 5 Jan 2026
Prime Loft of Main Street
Bar (on property)
Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook
Wright City
9.8 out of 10, Exceptional, (41)
"Had a good golf day wonderful place to stay "
United States
david c.
The price is HK$490
HK$1,354 total
includes taxes & fees
27 Dec - 28 Dec
Studio Condo on the Water @ Innsbrook
TV, books
St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (136)
"This was such a cute historical home and was perfect for our weekend in St Charles!"
United States
Isabelle C.
The price is HK$1,081
HK$2,100 total
includes taxes & fees
28 Dec - 29 Dec
St. Charles 1860's Gem - Sleeps 6!
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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Top Winfield Hotel Reviews

Drury Inn & Suites St. Louis St. Peters

Drury Inn & Suites St. Louis St. Peters

10/10 Excellent
"Yes"
Don 1-night trip
Posted 3 days ago
Drury Inn & Suites St. Louis St. Peters

Find out more about Winfield

Search for holiday rentals in Winfield on Expedia! You can easily find your home rentals, villas, holiday apartments in Winfield using one of the methods below:

  • View our selection of featured holiday rentals in Winfield
  • Use the map to find apartments and other holiday homes in the Winfield neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Winfield while they last

Look no further and take a look at our great range of rental properties in Winfield!

Frequently asked questions

Can I find holiday rentals in Winfield?

Yes, there are holiday rentals close to the most popular sights in Winfield, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Winfield has to offer?

Stunning 1890's Home - Sleeps 8! : This holiday home rental outside of Winfield is equipped with a BBQ, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a stovetop and a microwave, so that you can cook with friends or family.

How many holiday rentals are there in Winfield?

With 4 Expedia holiday rentals, you're guaranteed to find just the right place for your Winfield stay.

What can I see and do in Winfield?

Explore the area and family-friendly sights such as Raging Rivers Waterpark, or get out into nature at a spot like Mississippi River. Cuivre River State Park and CarShield Field are a couple of places you'll find in the wider area.

What are holiday rentals like in Winfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winfield. Holiday rentals provide amenities such as kitchens and laundry facilities so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies bustling with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a great option for family trips.