Winfield Holiday Rentals

  • Plan, book, stay with confidence

  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

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

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

Spacious*Outdoor Space*Modern*Family*Groups*Modern*Artistic

9.8 out of 10, Exceptional, (34)
"Two night stay to visit grandkids and inlaws. House was perfect for 7of us. Enjoyed decore and location. Owner provided a bit of Christmas flair. Bedrooms all upstairs and good size. Kitchen living and dining semi open. Home was comfortable and in quiet estabidmshed residential neighboriod. "
The price is AU$564
includes taxes & fees
14 Jan - 15 Jan
Spacious*Outdoor Space*Modern*Family*Groups*Modern*Artistic

The Lofts of North Main Street

9.6 out of 10, Exceptional, (120)
"This was a nice place to stay, clean, two bathrooms, plenty of beds . Close to all the shops. We met up with family and enjoyed the Christmas parade as well as lunch and supper right on Main St. "
The price is AU$393
includes taxes & fees
20 Jan - 21 Jan
The Lofts of North Main Street

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

10.0 out of 10, Exceptional, (193)
"Host and house were both great. "
1830's Luxury Brick Cottage, Cozy Fireplace, right off the Cobblestone Streets!

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

10.0 out of 10, Exceptional, (21)
"We had a great time with family and friends! The house was so cute and had everything we needed. Including coffee and tea started pods! "
Newly Updated Charming and Cozy Home near Historic Main Street in Frenchtown.

Stunning 1890's Home - Sleeps 8!

10.0 out of 10, Exceptional, (44)
"Just the perfect amount of space for our family. Great location. Beautiful home"
Stunning 1890's Home - Sleeps 8!

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

10.0 out of 10, Exceptional, (249)
"The property was perfect for our 2 day shopping trip. Only a half block from all the shops and restaurants. House is very unique and beautifully decorated."
1870's Luxury Guest Cottage, Historic Downtown St. Charles, Mo.

🌟 Adorable Historic 🏠 in the ❤️ of St. Charles 🌟

9.8 out of 10, Exceptional, (57)
"The house is charming, late 18th century, in a lovely neighborhood. Queen beds only accessible from one side due to being against walls on both levels. Additional towels required search, and limited for kitchen. Listing has occupancy as 7 - but insufficient 3 piece silverware for one full meal for that number, so washing required even if only 4 for 2 meals a day.. Kitchen cookware quite adequate but preparation bowls and storage boxes are limited. Charming holiday decorations, placemats,...
🌟 Adorable Historic 🏠 in the ❤️ of St. Charles 🌟

Luxurious couples retreat just steps from Historic Main Street in St. Charles!

10.0 out of 10, Exceptional, (79)
"My wife and I stayed here for two nights and enjoyed the property and surrounding area so much. The property was so cozy and inviting. We especially loved coming into the warm gas fire after exploring the shops that line the streets of St. Charles.The owners were also a pleasure to work with and they were very accommodating."
Luxurious couples retreat just steps from Historic Main Street in St. Charles!

1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard!

10.0 out of 10, Exceptional, (205)
"This was a perfect, cozy retreat. Super clean, well-appointed, and just steps from old main street in Saint Charles. Impressive!"
1790's Renovated Barn, Main Street St. Charles, Hot Tub in private backyard!

Clark Brick House w/ Pool - Historic St. Charles

9.8 out of 10, Exceptional, (82)
"The house was wonderful!"
Clark Brick House w/ Pool - Historic St. Charles

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

9.8 out of 10, Exceptional, (31)
"Great location, communication with the property owner and ease of check in. However, there were spots on the baseboards, walls, and rugs that were dusty/dirty. Found a ball of pet hair on one of the comforters. Overall, good stay but could have been cleaned better."
The robin nest a cozy cottage on historic main street; pet Friendly

Prime Loft of Main Street

9.8 out of 10, Exceptional, (82)
"Fantastic place and location!"
The price is AU$384
includes taxes & fees
13 Jan - 14 Jan
Prime Loft of Main Street

St. Charles 1860's Gem - Sleeps 6!

9.8 out of 10, Exceptional, (83)
"The house was adorable, clean, great location close to Main St. Highly recommend!"
The price is AU$400
includes taxes & fees
13 Jan - 14 Jan
St. Charles 1860's Gem - Sleeps 6!

Farmhouse 80 Acres Rec Room Peddle Boat Lake Fishing Nature Trl 2 ml to Grafton

10.0 out of 10, Exceptional, (109)
"From the get go the property felt angelic and peaceful. With the Loud World this is exactly what a person needs to find their Peace and Joy! Thank you ladies!!"
The price is AU$534
includes taxes & fees
13 Jan - 14 Jan
Farmhouse 80 Acres Rec Room Peddle Boat Lake Fishing Nature Trl 2 ml to Grafton

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

10.0 out of 10, Exceptional, (229)
"Such a beautiful home! We had a wonderful time over the holidays. The home was beautifully decorated. Highly recommended stay :)"
Charming Cottage on Main St. in Historic St. Charles! Jetted Tub, 2 Fireplaces!!

Innsbrook Luxe Escape

10.0 out of 10, Exceptional, (59)
"The space is really well set up not just for a lot of people to sleep at, but to spend time together as well. Our group all fit comfortably at the dinner table and around the fire pit. And the area around the house is gorgeous! "
Innsbrook Luxe Escape

Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

9.6 out of 10, Exceptional, (29)
" ."
The price is AU$500
includes taxes & fees
13 Jan - 14 Jan
Historic*Unique*Downtown*Quiet*Bright*Cheerful*Getaway

Confluence Cabin Grafton, IL

10.0 out of 10, Exceptional, (24)
"Nice property and host. "
The price is AU$342
includes taxes & fees
17 Jan - 18 Jan
Confluence Cabin Grafton, IL
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.
Don't see what you're looking for?
See all available properties in Winfield
Save an average of 15% on thousands of hotels when you're signed in

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, (1770)
"Nice room. Fun slot games"
The price is AU$185
includes taxes & fees
14 Jan - 15 Jan
Hollywood Casino & Hotel St. Louis

Ameristar Casino Resort and Spa

4.5 star property
8.4 out of 10, Very good, (1007)
"Our state was just amazing. We were very impressed with our room and the customer service."
The price is AU$349
includes taxes & fees
20 Jan - 21 Jan
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.

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?

The St. Charles Guest House, lovely historic home, fun for families and groups: This holiday home rental outside of Winfield is located on a river, and has a fireplace, a selection of games and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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. CarShield Field and Pere Marquette State Park 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.