Winfield Holiday Rentals

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Holiday Rentals in Winfield

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

9.8 out of 10, Exceptional, (129)
"My family loved staying at the house! my kids loved seeing the birds on the water and thought the hide-a-bed was the coolest thing ever! the view was beautiful and the cookies were the best we’ve ever had! The host was very helpful and very kind. We would definitely stay here again! "
Spacious Riverfront Perch/Easy Access to St.Charles less than 1 Hr to St. Louis

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (36)
"Super cute house, clean and within easy walking distance of historic main street"
Stunning 1890's Home - Sleeps 8!

1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

10.0 out of 10, Exceptional, (192)
"Host and house were both great. "
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

Residence on the Roundabout

9.6 out of 10, Exceptional, (116)
"Enjoyed the comfort of this little house while we explored all there is to do in St Charles "
Residence on the Roundabout

The Lofts of North Main Street

9.6 out of 10, Exceptional, (112)
"Loved the vibe, location couldn’t have been better. The unit was clean and had everything we needed. "
The price is AU$414
includes taxes & fees
4 Dec - 5 Dec
The Lofts of North Main Street

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

10.0 out of 10, Exceptional, (120)
"Sisters and sisterinlaws who take trips together had a fabulous time! House is great, clean and decorated nicely. Loved walking to shopping. Loved Lewis & Clark restaurant, Magpies, and Bradden 1818."
The St. Charles Guest House, lovely historic home, fun for families and groups

The robin nest a cozy cottage on historic main street; pet Friendly

9.8 out of 10, Exceptional, (29)
"Excellent location, great communication with property manager and terrific unit!"
The robin nest a cozy cottage on historic main street; pet Friendly

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

9.8 out of 10, Exceptional, (20)
"This was a great location for a girls weekend visiting St Charles. It is just down the road from Frenchtown and Main St which were really fun to bop around all the shops. The house was very clean, comfortable beds, and the patio area was super cute. Would absolutely stay here again!"
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.

Mansion 301 · 1st Capitol Mansion Boutique Hotel - Suite 301

8.6 out of 10, Excellent, (7)
"Very cute little place! "
The price is AU$242
includes taxes & fees
3 Dec - 4 Dec
Mansion 301 · 1st Capitol Mansion Boutique Hotel - Suite 301

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

10.0 out of 10, Exceptional, (57)
"Kim was a fantastic host with great communication. The home was just as presented. Location, space and bubble tent was perfect for our girls trip. "
Walk to St Charles Main St. Shops, Eateries & Bars! Bubble Tent!

Spacious, Beautiful St. Charles Home-Remodeled-Sleeps 10! New Patio!

10.0 out of 10, Exceptional, (43)
"I would give this property 4 and a half stars if I could do that. Our group of six (3 couples) enjoyed our stay in this spacious home. We especially appreciated the large table to gather around for meals and games and conversation. Nicely decorated living room/dining area. Checking in was easy. The kitchen had all the supplies we needed. The interior met our needs well, but the exterior could use a little TLC, especially the right hand rail. Would I stay here again? Absolutely yes! Would I...
The price is AU$630
includes taxes & fees
3 Dec - 4 Dec
Spacious, Beautiful St. Charles Home-Remodeled-Sleeps 10! New Patio!

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (79)
"I chose this property for the location, but would go back for the comfort and coziness of the home. The house included everything you could need in the kitchen and bathroom and made the trip very easy. It was very clean and very well organized. The offstreet parking was a plus. Highly recommend, Especially if you want something close to the Lindenwood campus and the downtown area."
The price is AU$381
includes taxes & fees
9 Dec - 10 Dec
St. Charles 1860's Gem - Sleeps 6!

Charming Cottage on Main St. in Historic St. Charles! Jetted Tub, 2 Fireplaces!!

10.0 out of 10, Exceptional, (228)
"Absolutely perfect location for everything, we will be coming back."
Charming Cottage on Main St. in Historic St. Charles! Jetted Tub, 2 Fireplaces!!

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

9.8 out of 10, Exceptional, (37)
"We absolutely loved this cozy property. It had everything we needed and was very clean. The location is amazing - a great place if you like to walk. Great views! The owner was easy to get a hold of and responded super quickly. Would absolutely recommend!"
The Cardinal Nest A Cozy Cottage on Historic Main Street; Pet Friendly

Newly Remodeled Home - Sleeps 9!

10.0 out of 10, Exceptional, (16)
"The interior is super clean, showers all very nice, and beds seemed like they have never been slept in. I highly recommend this place, the kitchen is well suited for cooking anything! "
The price is AU$630
includes taxes & fees
3 Dec - 4 Dec
Newly Remodeled Home - Sleeps 9!

The Chic Chalet

10.0 out of 10, Exceptional, (16)
"Beautiful property. Relaxing in nature surrounded by wildlife and very peaceful."
The Chic Chalet

Perfect Weekend Getaway! Condo With Great River Views! Pool!

9.8 out of 10, Exceptional, (126)
"Awesome place to stay especially if you're drinking and don't want to drive home. "
The price is AU$309
includes taxes & fees
6 Dec - 7 Dec
Perfect Weekend Getaway! Condo With Great River Views! Pool!

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

10.0 out of 10, Exceptional, (246)
"We had a wonderful weekend in this historic home! We were greeted by a beautiful Christmas tree in the window!! When we walked in the home it was decorated ready for Christmas. The location is right in the historic district and is perfect to walk to shops and restaurants! I truly wish we could have spent more time in this special home! We would love to come back again!"
1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.

The Lewis & Clark Hangout

9.2 out of 10, Wonderful, (9)
"The location was perfect - we loved the house - the host was very responsive. A very good and very fun overnight trip!"
The price is AU$619
includes taxes & fees
1 Jan - 2 Jan 2025
The Lewis & Clark Hangout

Mansion 302 · 1st Capital Mansion Boutique Hotel - Suite 302

9.4 out of 10, Exceptional, (6)
"I love the The two lions statues heads when you pulled up to it with the lions head also love the old wood to stay in glass windows, and all the rooms! and I know it’s probably over 100 years old. It’s like the house that we bought years ago and the country was over 100 years old.!"
The price is AU$277
includes taxes & fees
3 Dec - 4 Dec
Mansion 302 · 1st Capital Mansion Boutique Hotel - Suite 302
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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Other types of properties in Winfield you may be interested in

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

9.8 out of 10, Exceptional, (129)
"My family loved staying at the house! my kids loved seeing the birds on the water and thought the hide-a-bed was the coolest thing ever! the view was beautiful and the cookies were the best we’ve ever had! The host was very helpful and very kind. We would definitely stay here again! "
Spacious Riverfront Perch/Easy Access to St.Charles less than 1 Hr to St. Louis

Hollywood Casino & Hotel St. Louis

3.5 star property
8.4 out of 10, Very good, (1707)
"Nice property however cleanliness could certainly improved. "
The price is AU$195
includes taxes & fees
3 Dec - 4 Dec
Hollywood Casino & Hotel St. Louis

Ameristar Casino Resort and Spa

4.5 star property
8.2 out of 10, Very good, (1007)
"If you have a taste for a more lavish stay it’ll beat the embassy or Hyatt any day"
The price is AU$311
includes taxes & fees
3 Dec - 4 Dec
Ameristar Casino Resort and Spa
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

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?

Residence on the Roundabout: This holiday home rental outside of Winfield is located on a river, and has a balcony, a garden and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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.