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Winfield Holiday Rentals

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Check prices for these dates

In two weeks
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Winfield holiday rentals

A cozy living room with a brown leather couch, a wooden spiral staircase, and large windows offering a view of the outdoors.

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

The Nest, unplug& reconnect with that special someone in our charming birdhouse!
Troy
9.4 out of 10, Exceptional, (55 reviews)
"Was very clean, great little spot for a weekend get away. Was everything they said it was."
United States
Dillon E.
The price is HK$1,334
HK$1,630 total
includes taxes & fees
13 Oct - 14 Oct
The Nest, unplug& reconnect with that special someone in our charming birdhouse!
A modern kitchen with white cabinets, a black refrigerator, a stainless steel microwave, and a black oven. There are four blue bowls on a wooden table with a woven placemat.

2. 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.
The price is HK$984
HK$2,114 total
includes taxes & fees
13 Oct - 14 Oct
Quiet 2BR Retreat on 7 Acres | Sleeps 6, Fast WiFi
A residential house with a garage, a driveway, and a parked trailer.

3. Cozy 1-bedroom studio in tranquil Moscow Mills with AC

Cozy 1-bedroom studio in tranquil Moscow Mills with AC
Moscow Mills
The price is HK$1,370
HK$1,630 total
includes taxes & fees
8 Oct - 9 Oct
Cozy 1-bedroom studio in tranquil Moscow Mills with AC
A living room with a sofa, coffee table, and patterned rug. There is a dining area with a bar and stools.

4. Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters

Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
St. Peters
10.0 out of 10, Exceptional, (18 reviews)
"Excellent place to stay while visiting. Pet friendly a HUGE plus. The host was very pleasant to work with and the place really is thoughtfully outfitted. Would definitely stay here again"
United States
Chris B.
The price is HK$672
HK$2,184 total
includes taxes & fees
14 Oct - 15 Oct
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
A rustic bar area with stone walls, wooden chairs, and hanging pendant lights.

5. Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook
Wright City
9.8 out of 10, Exceptional, (70 reviews)
"everything was clean and really beautiful, we enjoyed the stay "
United States
Vanessa O.
The price is HK$628
HK$1,577 total
includes taxes & fees
13 Oct - 14 Oct
Studio Condo on the Water @ Innsbrook
A marina with boats docked, a waterfront restaurant, and a building with a green roof.

6. Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort
Grafton
9.8 out of 10, Exceptional, (73 reviews)
"It is a very nice place to stay. Rooms were clean and the place is in a very good location."
United States
Tanmoy D.
The price is HK$883
HK$2,499 total
includes taxes & fees
13 Oct - 14 Oct
Riverside Home - Modern meets comfort
A spacious kitchen with white cabinets, a central island with bar stools, a stainless steel refrigerator, and a microwave.

7. 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, (55 reviews)
"It was a perfect choice for our family to celebrate Christmas. "
United States
Leanne S.
The price is HK$1,083
HK$3,420 total
includes taxes & fees
21 Oct - 22 Oct
Spacious, 3 bedroom home, finished basement on quiet court
A room with a dark wooden wall, a brown leather sofa, a white door, and a patterned wall.

8. Stylish1BRStudioCleanQuietandCozy

Stylish1BRStudioCleanQuietandCozy
Saint Charles
10.0 out of 10, Exceptional, (3 reviews)
"Room was very clean with little to no issues at all. Host was super easy to work with and get information from. This spot is within 15-20minutes OR LESS to anything you’d need to do in the ofallon and surrounding areas. I’d book it again if I needed to."
United States
Mike S.
The price is HK$746
HK$2,170 total
includes taxes & fees
8 Oct - 9 Oct
Stylish1BRStudioCleanQuietandCozy
A dining area with a round table and chairs, a bench, and a painting on the wall.

9. Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio

Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
Troy
10.0 out of 10, Exceptional, (1 review)
"We came in town for the fair and this place was a very beautiful place. Very clean and very well decorated. It was the perfect place to stay in Troy. The host was very nice and could be reached instantly if we had any issues."
United States
Unspecified B.
The price is HK$1,350
HK$3,088 total
includes taxes & fees
29 Oct - 30 Oct
Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
A living room with a fireplace, two armchairs, a potted plant, and a door with a window.

10. The Great Room - fully cozy & private Townhome

The Great Room - fully cozy & private Townhome
Saint Charles
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful and decorated well. Our experience was great and i recommend this rental. Would be nice if they honored military discount as I am a veteran. "
United States
Rodney M.
The price is HK$957
HK$2,164 total
includes taxes & fees
24 Oct - 25 Oct
The Great Room - fully cozy & private Townhome
A bedroom with two beds, a desk, and a chair.

11. Rafton Inn Vacation Cottage 93

Rafton Inn Vacation Cottage 93
Grafton
9.8 out of 10, Exceptional, (7 reviews)
"Great place & location. Very clean & accommodating."
United States
Mike F.
The price is HK$1,177
HK$2,603 total
includes taxes & fees
8 Oct - 9 Oct
Rafton Inn Vacation Cottage 93
A cozy living room with a brick wall, a white sofa with colorful cushions, a small black table, and a potted plant.

12. Prime Loft of Main Street

Prime Loft of Main Street
St. Charles Historic District
9.8 out of 10, Exceptional, (120 reviews)
"Host was great. The cutest place in the perfect spot! "
United States
Anonymous traveller
The price is HK$764
HK$1,775 total
includes taxes & fees
8 Oct - 9 Oct
Prime Loft of Main Street
A dining area with a table and chairs, a ceiling fan, and a wall-mounted flower painting.

13. The Cozy Family Retreat

The Cozy Family Retreat
O'Fallon
7.8 out of 10, Good, (26 reviews)
"Location was great, potential was unabated. Execution was absolutely terrible. "
United States
clint a.
The price is HK$918
HK$2,502 total
includes taxes & fees
13 Oct - 14 Oct
The Cozy Family Retreat
A rustic bar area with stone walls, wooden chairs, and hanging pendant lights.

14. Lakefront Studio Condo

Lakefront Studio Condo
Wright City
9.8 out of 10, Exceptional, (35 reviews)
"The room was clean and beautiful, we really enjoyed the stay "
United States
Vanessa O.
The price is HK$883
HK$1,968 total
includes taxes & fees
20 Oct - 21 Oct
Lakefront Studio Condo
A spacious living area with a wooden floor, a dining table with chairs, a flat-screen TV mounted on the wall, and a kitchen area with modern appliances.

15. The Lofts of North Main Street

The Lofts of North Main Street
St. Charles Historic District
9.6 out of 10, Exceptional, (194 reviews)
"Very comfortable bed. Well stocked kitchen. Nice covered porch. Great neighborhood."
United States
Carla K.
The price is HK$1,091
HK$2,183 total
includes taxes & fees
12 Oct - 13 Oct
The Lofts of North Main Street
Living area

16. 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.
The price is HK$1,766
HK$3,759 total
includes taxes & fees
12 Oct - 13 Oct
Family Friendly w/ Game Room in Quiet Neighborhood
A wooden deck with two blue chairs and a small round table, overlooking a backyard with a pool and a grassy lawn.

17. Aeries Villas 309 A

Aeries Villas 309 A
Grafton
9.0 out of 10, Wonderful, (2 reviews)
"The location was excellent, with beautiful views overlooking the town and the river. Jeff was an outstanding host—very responsive, communicative, and easy to work with throughout our stay.The property is conveniently located within walking distance of the city center, making it easy to explore the area. Our favorite part, however, was the back porch and balcony. It was the perfect place to relax, and each day we were treated to the sight of a family of deer spending time in the backyard. It made...
United States
Josh G.
The price is HK$1,726
HK$2,149 total
includes taxes & fees
9 Oct - 10 Oct
Aeries Villas 309 A
A modern kitchen with dark green cabinets, a stainless steel refrigerator, and a dining area with a dark wooden table and black chairs.

18. 3BR Close to Historic Main Street-Low Cleaning Fee

3BR Close to Historic Main Street-Low Cleaning Fee
Saint Charles
The price is HK$742
HK$2,104 total
includes taxes & fees
18 Oct - 19 Oct
3BR Close to Historic Main Street-Low Cleaning Fee
A hallway with a wooden wall, a door leading to a bedroom, and a staircase.

19. St. Charles 1860's Gem - Sleeps 6!

St. Charles 1860's Gem - Sleeps 6!
St. Charles Historic District
9.8 out of 10, Exceptional, (166 reviews)
"Very nice very clean property. Very much enjoyed our stay"
United States
Joe R.
The price is HK$953
HK$2,104 total
includes taxes & fees
11 Oct - 12 Oct
St. Charles 1860's Gem - Sleeps 6!
A hotel pool area with a rectangular pool, lounge chairs, and a wooden bench.

20. 1 Bedroom | Pool & Gym. Free Breakfast

1 Bedroom | Pool & Gym. Free Breakfast
O'Fallon
8.4 out of 10, Very good, (5 reviews)
"It’s a suite hotel - rooms were very spacious. It’s in a great location. Staff is welcoming and kind. It was exactly what we needed for a last minute trip to check on family."
United States
Melinda C.
The price is HK$1,167
HK$1,550 total
includes taxes & fees
11 Oct - 12 Oct
1 Bedroom | Pool & Gym. Free Breakfast
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

Sleep Inn & Suites O'Fallon MO - Technology Drive

Sleep Inn & Suites O'Fallon MO - Technology Drive

10/10 Excellent
"It was close to everything"
Christina 1-night trip
Posted 17 hours ago
Sleep Inn & Suites O'Fallon MO - Technology Drive

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?

HotTub-2br2b-near Historic Main Street: This holiday home rental outside of Winfield offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of Access to hot tub in this rental home to help you unwind.

How many holiday rentals are there in Winfield?

With 3 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.