Winfield Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • 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

Our top choices for Winfield holiday rentals

9.8 out of 10, Exceptional, (147)
"This was a great place to stay. Clean, quiet and very welcoming! I would definitely stay again and recommend!"
United States
johnna T.
Spacious Riverfront Perch/Easy Access to St.Charles less than 1 Hr to St. Louis
9.6 out of 10, Exceptional, (37)
"Great hosts, great stay, always enjoy my time"
United States
Anonymous traveller
The price is AU$318
includes taxes & fees
21 Dec - 22 Dec
Owl house was built for unplugging, relaxing & connecting with friends/family
2.0 star property
Winter SALE NOW, Luxe stay, Private, HUGE Game Rm, Hot Tub, .67 acres
10.0 out of 10, Exceptional, (136)
"We loved staying here in this adorable clean house that was only 1 block off of downtown Main Street shopping. "
United States
Lisa S.
The St. Charles Guest House, lovely historic home, fun for families and groups

Aparthotel in St. Charles Historic District

The Otter Suite at Divine Otter
9.0 out of 10, Wonderful, (7)
"Great Location near many bars and restaurants on a very cool street that hosts many events and festivals. "
United States
Ryan C.
The Otter Suite at Divine Otter

Holiday Home in St. Charles Historic District

Honky Tonk Hideaway
8.8 out of 10, Excellent, (13)
"Great location close to historic district."
United States
Hugh S.
The price is AU$476
includes taxes & fees
25 Dec - 26 Dec
Honky Tonk Hideaway
9.2 out of 10, Wonderful, (31)
"House and yard were great! Loved the location."
United States
Jennifer P.
Charming open 4bd and screen-in porch! Sleeps 10!
10.0 out of 10, Exceptional, (11)
"The property was beautiful. Loved taking my morning coffee down to the dock each morning. "
United States
Andy Y.
Charming 4-bedroom chalet with lake access in enchanting Innsbrook.

Holiday Home in St. Charles Historic District

St. Charles 1860's Gem - Sleeps 6!
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 AU$414
includes taxes & fees
28 Dec - 29 Dec
St. Charles 1860's Gem - Sleeps 6!

Apartment in St. Charles Historic District

Cozy Clark Suite in Frenchtown Saint Charles
9.6 out of 10, Exceptional, (14)
"Awesome place to stay"
United States
paul
Cozy Clark Suite in Frenchtown Saint Charles

Holiday Home in St. Charles Historic District

🌟 Adorable Historic 🏠 in the ❤️ of St. Charles 🌟
9.8 out of 10, Exceptional, (76)
"Great location, lovely house.Easy to find restaurants, places to shop and nice area for strolling."
United States
Dianne P.
🌟 Adorable Historic 🏠 in the ❤️ of St. Charles 🌟

Holiday Home in St. Charles Historic District

The Lewis & Clark Hangout
9.0 out of 10, Wonderful, (19)
"Excellent location and a great space for 4 couples. The beds were exceptionally comfortable! "
United States
Kimberly C.
The price is AU$554
includes taxes & fees
22 Dec - 23 Dec
The Lewis & Clark Hangout
9.6 out of 10, Exceptional, (62)
"We had a great weekend and enjoyed the house very much! We had everything we needed!"
United States
Laurie S.
The price is AU$748
includes taxes & fees
22 Dec - 23 Dec
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!

Holiday Home in St. Charles Historic District

Madison House 1 -Walk to Main St
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 AU$360
includes taxes & fees
22 Dec - 23 Dec
Madison House 1 -Walk to Main St
9.8 out of 10, Exceptional, (26)
"The place was great! "
United States
Melissa I.
Home Near Main Street-Covered Patio-Hot Tub!
9.4 out of 10, Exceptional, (40)
"It was very clean and manageable was nice. I stayed in the Bird house. "
United States
Connie T.
The price is AU$318
includes taxes & fees
21 Dec - 22 Dec
The Nest, reconnect with that special someone in our charming birdhouse!
9.6 out of 10, Exceptional, (65)
"Very quiet neighborhood and very nice place. "
United States
wendy p.
The price is AU$596
includes taxes & fees
23 Dec - 24 Dec
Spacious*Outdoor Space*Modern*Family*Groups*Modern*Artistic

Holiday Home in St. Charles Historic District

Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
9.6 out of 10, Exceptional, (58)
"Nice property. Clean. "
United States
Belinda J.
The price is AU$485
includes taxes & fees
31 Dec - 1 Jan 2026
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway
10.0 out of 10, Exceptional, (211)
"Nice view of the Mississippi in the morning. Just off of the main street in old town St Charles, this place was perfect for our needs."
United States
Ralph
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!
9.8 out of 10, Exceptional, (54)
"A great property very quiet and clean home . The neighborhood is very safe and i highly recommend "
United States
Anonymous traveller
The price is AU$783
includes taxes & fees
21 Dec - 22 Dec
Spacious, Beautiful St. Charles Home-Remodeled-Sleeps 10! New Patio!
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

Everything you need to know about Winfield holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Winfield holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Winfield holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winfield holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winfield. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winfield holiday rentals we have selected for you start as low as AU$318 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winfield rentals

At Expedia, we put the best Winfield holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Winfield rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Winfield holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Winfield. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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.