Default HTG hotel image

Winfield Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Sep 4 - Sep 6
In two months
Oct 16 - Oct 18
In three months
Nov 13 - Nov 15
In four months
Dec 11 - Dec 13

Our top choices for Winfield vacation rentals

Living area

1. The Nest, reconnect with that special someone in our charming birdhouse!

The Nest, reconnect with that special someone in our charming birdhouse!
Troy
9.4 out of 10, Exceptional, (49 reviews)
"Was very clean, great little spot for a weekend get away. Was everything they said it was."
United States
Dillon E.
$195 nightly
The price is $208
Aug 18 - Aug 19
Total with taxes and fees
The Nest, reconnect with that special someone in our charming birdhouse!
Exterior

2. 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, (147 reviews)
"My wife and I stayed there for a few days for her birthday. It was so peaceful there. The host keeps the place very clean and includes many additional thoughtful items. The trail is a nice touch and worth exploring. It was super hot during our stay and the A/C kept us nice and cool."
United States
Alex
$272 nightly
The price is $301
Aug 18 - Aug 19
Total with taxes and fees
Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton
2 bedrooms, desk, iron/ironing board, WiFi (free)

3. Pet-Friendly 2BR Townhome | Workspace

Pet-Friendly 2BR Townhome | Workspace
O Fallon
9.8 out of 10, Exceptional, (15 reviews)
"Great quiet neighborhood close to everything!"
United States
Jen D.
$334 nightly
The price is $366
Aug 20 - Aug 21
Total with taxes and fees
Pet-Friendly 2BR Townhome | Workspace
Marina

4. Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort
Grafton
10.0 out of 10, Exceptional, (69 reviews)
"Clean, quiet and convenient place to stay. Would definitely recommend this place!"
United States
Kathy K.
$309 nightly
The price is $327
Sep 2 - Sep 3
Total with taxes and fees
Riverside Home - Modern meets comfort
Interior

5. Spacious, 3 bedroom home, finished basement on quiet court

Spacious, 3 bedroom home, finished basement on quiet court
St. Peters
9.8 out of 10, Exceptional, (54 reviews)
"This was our second stay, and like the first, everything was clean and comfortable. Homeowner was very responsive to some last minute questions that I had leading up to the trip which was much appreciated. Will definitely stay again in the future! "
United States
Rachel P.
$336 nightly
The price is $389
Aug 24 - Aug 25
Total with taxes and fees
Spacious, 3 bedroom home, finished basement on quiet court
Dining

6. Renovated 5BR | Group Space + Large Yard

Renovated 5BR | Group Space + Large Yard
Wentzville
10.0 out of 10, Exceptional, (17 reviews)
"Great place and people really helped the stay"
United States
Rustin N.
$564 nightly
The price is $592
Aug 25 - Aug 26
Total with taxes and fees
Renovated 5BR | Group Space + Large Yard
Coffee/tea maker, fridge, microwave, oven

7. RAFTON INN VACATION RENTAL

RAFTON INN VACATION RENTAL
Grafton
9.4 out of 10, Exceptional, (13 reviews)
"Best place we have stayed in Grafton so far! Easy walk location to everything! We were very pleased with this VRBO!"
United States
Renee M.
$1,011 nightly
The price is $1,071
Aug 18 - Aug 19
Total with taxes and fees
RAFTON INN VACATION RENTAL
Coffee/tea maker, fridge, microwave, oven

8. Quiet 2BR Retreat on 7 Acres | Sleeps 6, Fast WiFi

Quiet 2BR Retreat on 7 Acres | Sleeps 6, Fast WiFi
Moscow Mills
10.0 out of 10, Exceptional, (14 reviews)
"Great place, nice neighborhood. "
United States
Julie L.
$292 nightly
The price is $292
Sep 16 - Sep 17
Total with taxes and fees
Quiet 2BR Retreat on 7 Acres | Sleeps 6, Fast WiFi
1 bedroom, WiFi

9. Rafton Inn Vacation Cottage 19

Rafton Inn Vacation Cottage 19
Grafton
10.0 out of 10, Exceptional, (5 reviews)
"Everything was great!"
United States
Barbara A.
$315 nightly
The price is $334
Aug 18 - Aug 19
Total with taxes and fees
Rafton Inn Vacation Cottage 19
Outdoor spa tub

10. Main Street Cottage with Hot Tub

Main Street Cottage with Hot Tub
Grafton
9.0 out of 10, Wonderful, (7 reviews)
"We really enjoyed the space!"
United States
Ian P.
$292 nightly
The price is $314
Aug 18 - Aug 19
Total with taxes and fees
Main Street Cottage with Hot Tub
Private kitchen

11. Centrally located, spacious 4 bdrm, on quiet Ct

Centrally located, spacious 4 bdrm, on quiet Ct
O'Fallon
10.0 out of 10, Exceptional, (25 reviews)
"The house was very nice,close to everything and on a quiet cul-du-sac.the host was very nice and helpful.would definitely stay again.as a matter of fact we were there for work and are planning on staying again for another couple weeks! "
United States
Patrick S.
$350 nightly
The price is $405
Aug 24 - Aug 25
Total with taxes and fees
Centrally located, spacious 4 bdrm, on quiet Ct
Interior

12. Rafton 2 Home

Rafton 2 Home
Grafton
9.6 out of 10, Exceptional, (5 reviews)
"Owner was so easy to work with and the location was perfect. Great house for our girls trip!"
United States
Michelle S.
$686 nightly
The price is $727
Aug 18 - Aug 19
Total with taxes and fees
Rafton 2 Home
Exterior detail

13. The Crimson Caboose! Unique, one of a kind experience in downtown, Grafton

The Crimson Caboose! Unique, one of a kind experience in downtown, Grafton
Grafton
10.0 out of 10, Exceptional, (4 reviews)
"Had a fantastic trip! We recomend highly!"
United States
Jeremy B.
$400 nightly
The price is $424
Aug 18 - Aug 19
Total with taxes and fees
The Crimson Caboose! Unique, one of a kind experience in downtown, Grafton
Living area

14. Spacious 5-bedroom house in serene O'Fallon with AC

Spacious 5-bedroom house in serene O'Fallon with AC
O'Fallon
9.8 out of 10, Exceptional, (7 reviews)
"Nice place "
United States
RAMONA O E.
$571 nightly
The price is $611
Aug 18 - Aug 19
Total with taxes and fees
Spacious 5-bedroom house in serene O'Fallon with AC
Coffee/tea maker, fridge, microwave, oven

15. Spacious 4BR Home for Families & Pets

Spacious 4BR Home for Families & Pets
Wentzville
9.0 out of 10, Wonderful, (8 reviews)
"It was a perfect house for our family to stay in for the week. Great bedroom spaces, very nice kitchen. It’s in a cute area with some great restaurants and coffee shops within walking distance. "
United States
kristen l.
$458 nightly
The price is $504
Aug 25 - Aug 26
Total with taxes and fees
Spacious 4BR Home for Families & Pets
Smart TV, fireplace, computer monitors

16. Charming open 4bd and screen-in porch! Sleeps 10!

Charming open 4bd and screen-in porch! Sleeps 10!
Saint Charles
9.0 out of 10, Wonderful, (48 reviews)
"Great property, plenty of space, was very clean!"
United States
Will M.
$483 nightly
The price is $546
Aug 18 - Aug 19
Total with taxes and fees
Charming open 4bd and screen-in porch! Sleeps 10!
Dining

17. Cozy 3 Bedroom/ Family Comfort & Convenient Location

Cozy 3 Bedroom/ Family Comfort & Convenient Location
Wentzville
10.0 out of 10, Exceptional, (10 reviews)
"Great place to stay for the night"
United States
Jacob M.
$337 nightly
The price is $362
Aug 31 - Sep 1
Total with taxes and fees
Cozy 3 Bedroom/ Family Comfort & Convenient Location
Fireplace

18. 1870's Estate Style Home with private courtyard.

1870's Estate Style Home with private courtyard.
grafton
10.0 out of 10, Exceptional, (9 reviews)
"Very close in walking distance to all the downtown attractions. "
United States
Stacey G.
$690 nightly
The price is $748
Aug 18 - Aug 19
Total with taxes and fees
1870's Estate Style Home with private courtyard.
TV

19. Family Friendly w/ Game Room in Quiet Neighborhood

Family Friendly w/ Game Room in Quiet Neighborhood
Wentzville
10.0 out of 10, Exceptional, (2 reviews)
"Nice house for our week in Lake St. Louis area. Accurate description of what you are getting and clean house. Would stay again if we are back in the area"
United States
Campbell W.
$474 nightly
The price is $474
Sep 3 - Sep 4
Total with taxes and fees
Family Friendly w/ Game Room in Quiet Neighborhood
Smart TV

20. 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, (79 reviews)
"Spacious house and plenty of room in the long drive for everyone's cars which is rare! Would stay at again!"
United States
Matthew B.
$476 nightly
The price is $538
Aug 18 - Aug 19
Total with taxes and fees
New Remodel in St. Charles - Sleeps 10! New patio! Large Fenced-in backyard!
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winfield Hotel Reviews

Country Inn & Suites by Radisson, St. Charles Historic District

Country Inn & Suites by Radisson, St. Charles Historic District

10/10 Excellent
"We love this hotel. Very well kept and location is great. Only thing that would make it better is if we could bring our dog."
Victoria 1-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, St. Charles Historic District

Find out more about Winfield

Everything you need to know about Winfield vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Winfield vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Winfield vacation 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 low season months. For more hustle and bustle, you may prefer to visit Winfield in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $196 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Winfield rentals

At Expedia, we put the best Winfield vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Winfield?

Yes, we have vacation rentals near popular sights in Winfield, or you can select a secluded option if you want a relaxing place to stay.

What are some of the best vacation rentals in Winfield?

St. Charles 1860's Gem - Sleeps 6!: This vacation home rental near Winfield is located on a river and has a garden, a selection of books, and air-conditioning to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop.

How many vacation rentals are there in Winfield?

With 3 Expedia vacation rentals, you're sure 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. CarShield Field and Pere Marquette State Park are a couple of places you'll find in the larger area.

What are vacation rentals like in Winfield?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Winfield. Vacation rentals feature extras such as laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitized environment, a vacation rental can provide a sense of privacy away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for a small group gathering.