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Winfield Vacation Rentals

Check prices for these dates

In two weeks
Oct 30 - Nov 1
In two months
Dec 11 - Dec 13
In three months
Jan 8 - Jan 10
In four months
Feb 5 - Feb 7

Our top choices for Winfield vacation 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)
"The property was amazing perfect for a couple or a individual how wants to unplug."
United States
Jess H.
$194 nightly
The price is $207
Oct 18 - Oct 19
Total with taxes and fees
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.
$269 nightly
The price is $269
Oct 18 - Oct 19
Total with taxes and fees
Quiet 2BR Retreat on 7 Acres | Sleeps 6, Fast WiFi
A living room with a sofa, coffee table, and patterned rug. There is a dining area with a bar and stools.

3. 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, (20 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.
$252 nightly
The price is $280
Oct 18 - Oct 19
Total with taxes and fees
Private Entry Basement Suite • Pond & Farm View • Dog Friendly • St Peters
A kitchen with a stainless steel sink, a gold faucet, and a bottle of hand soap.

4. Wentzville King Bed Walk to Downtown!

Wentzville King Bed Walk to Downtown!
Wentzville
9.0 out of 10, Wonderful, (2 reviews)
"Most everything was good. I do recommend correcting the upward slope on the top of the step from the living area to the bedroom area. As you approach from the kitchen, the slight rise in the floor throws off your balance going down the step. Wrenched my back and legs when awkwardly hitting the lower level."
United States
Alan G.
$316 nightly
The price is $354
Oct 19 - Oct 20
Total with taxes and fees
Wentzville King Bed Walk to Downtown!
A dining area with a round table and chairs, a bench, and a painting on the wall.

5. 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.
$349 nightly
The price is $378
Oct 22 - Oct 23
Total with taxes and fees
Historic 2BR Home in Downtown Troy - King Bed, Fire Table & Patio
A hotel pool area with a rectangular pool, lounge chairs, and a wooden bench.

6. 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.
$137 nightly
The price is $158
Oct 18 - Oct 19
Total with taxes and fees
1 Bedroom | Pool & Gym. Free Breakfast
A room with a dark wooden wall, a brown leather sofa, a white door, and a patterned wall.

7. 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.
$238 nightly
The price is $265
Oct 19 - Oct 20
Total with taxes and fees
Stylish1BRStudioCleanQuietandCozy
A rustic bar area with stone walls, wooden chairs, and hanging pendant lights.

8. Studio Condo on the Water @ Innsbrook

Studio Condo on the Water @ Innsbrook
Wright City
10.0 out of 10, Exceptional, (72 reviews)
"everything was clean and really beautiful, we enjoyed the stay "
United States
Vanessa O.
$188 nightly
The price is $201
Oct 19 - Oct 20
Total with taxes and fees
Studio Condo on the Water @ Innsbrook
A bedroom with two beds, a desk, and a chair.

9. Rafton Inn Vacation Cottage 19

Rafton Inn Vacation Cottage 19
Grafton
10.0 out of 10, Exceptional, (7 reviews)
"Everything was great!"
United States
Barbara A.
$315 nightly
The price is $334
Oct 18 - Oct 19
Total with taxes and fees
Rafton Inn Vacation Cottage 19
A white house with a porch and a large tree in front.

10. 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, (153 reviews)
"Great place to get away and unwind."
United States
Rex P.
$274 nightly
The price is $302
Oct 18 - Oct 19
Total with taxes and fees
Our 80-Acre Farm, Lake, Nature Trail, Bonfires, Starry Nights 2 Miles Grafton
A hotel room with a large bed, a nightstand with a lamp, a painting on the wall, and a window with curtains.

11. Pet-Friendly 2BR Townhome | Workspace

Pet-Friendly 2BR Townhome | Workspace
O Fallon
9.8 out of 10, Exceptional, (17 reviews)
"Great quiet neighborhood close to everything!"
United States
Jen D.
$399 nightly
The price is $438
Nov 8 - Nov 9
Total with taxes and fees
Pet-Friendly 2BR Townhome | Workspace
A marina with boats docked, a waterfront restaurant, and a building with a green roof.

12. Riverside Home - Modern meets comfort

Riverside Home - Modern meets comfort
Grafton
9.8 out of 10, Exceptional, (74 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.
$316 nightly
The price is $335
Oct 21 - Oct 22
Total with taxes and fees
Riverside Home - Modern meets comfort
A modern kitchen with white cabinets, a stainless steel refrigerator, a large island with bar stools, and copper pendant lights.

13. Spacious 4BR Home for Families & Pets

Spacious 4BR Home for Families & Pets
Wentzville
9.0 out of 10, Wonderful, (8 reviews)
"Amazing for attending the fireworks festivals nearby. Great shops walking distance for coffee and food"
United States
Tom K.
$448 nightly
The price is $494
Oct 19 - Oct 20
Total with taxes and fees
Spacious 4BR Home for Families & Pets
Living area

14. Family Friendly w/ Game Room in Quiet Neighborhood

Family Friendly w/ Game Room in Quiet Neighborhood
Wentzville
10.0 out of 10, Exceptional, (3 reviews)
"Great location. Host quick to reply to questions!! Would stay here again."
United States
Dilauna B.
$479 nightly
The price is $479
Oct 19 - Oct 20
Total with taxes and fees
Family Friendly w/ Game Room in Quiet Neighborhood
An aerial view of a residential area with houses, a swimming pool, and a body of water.

15. Timber Ridge Hideaway 317 A | Cozy 1BR Grafton Stay

Timber Ridge Hideaway 317 A | Cozy 1BR Grafton Stay
Grafton
$218 nightly
The price is $240
Oct 18 - Oct 19
Total with taxes and fees
Timber Ridge Hideaway 317 A | Cozy 1BR Grafton Stay
A living room with a fireplace, two armchairs, a potted plant, and a door with a window.

16. 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.
$205 nightly
The price is $216
Oct 19 - Oct 20
Total with taxes and fees
The Great Room - fully cozy & private Townhome
A dining area with a wooden table, six chairs, a chandelier, and a modern kitchen in the background.

17. Renovated 5BR | Group Space + Large Yard

Renovated 5BR | Group Space + Large Yard
Wentzville
10.0 out of 10, Exceptional, (17 reviews)
"Great location, clean and well prepared property!"
United States
Jeff M.
$552 nightly
The price is $579
Oct 18 - Oct 19
Total with taxes and fees
Renovated 5BR | Group Space + Large Yard
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
$256 nightly
The price is $269
Oct 18 - Oct 19
Total with taxes and fees
3BR Close to Historic Main Street-Low Cleaning Fee
A rustic bar area with stone walls, wooden chairs, and hanging pendant lights.

19. 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.
$237 nightly
The price is $253
Oct 20 - Oct 21
Total with taxes and fees
Lakefront Studio Condo
A modern living room with a grey sofa, teal armchairs, a wooden coffee table, and a patterned rug.

20. Private Basement - Two King Beds and Hot Tub

Private Basement - Two King Beds and Hot Tub
Saint Charles
9.6 out of 10, Exceptional, (5 reviews)
"This property is the perfect get-away. Quite relaxing. The beds are super comfy the outside sitting area is quiet and relaxing. The interior is fully furnished very nice quality everything. And you are within 10 minutes of shopping and tons of restaurants. I hated to leave.Hope I can return."
United States
JoAnn C.
$307 nightly
The price is $343
Nov 1 - Nov 2
Total with taxes and fees
Private Basement - Two King Beds and Hot Tub
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

Hampton Inn St. Charles St. Peters

Hampton Inn St. Charles St. Peters

10/10 Excellent
"Fantastic place to stay! The staff was amazing!"
Catherine 1-night trip
Posted 4 hours ago
Hampton Inn St. Charles St. Peters

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 $201 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?

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

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. Cuivre River State Park and CarShield Field 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.