Winfield Holiday Rentals

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Holiday Rentals in Winfield

Spacious open concept home w/ game room + firepit

9.8 out of 10, Exceptional, (48)
"Our family of 4 had a wonderful stay here! Great neighborhood and a spacious home! The beds were super comfy & the home was decorated nicely! Thank you for having us Amanda! We’ll be back :) "
Spacious open concept home w/ game room + firepit

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (71)
"Plenty of space. Great location. We enjoyed our stay very much. My only suggestion would be go in the day before guest check in and make sure everything smells and looks clean. "
Furnished Private home in Aurora sleeps 9 guests

Chic Suite/Mins to L Train /Laundry/Free Parking

9.6 out of 10, Exceptional, (35)
"Had a great stay! Thank you!"
Chic Suite/Mins to L Train /Laundry/Free Parking

Historic Oak Park Residence

2.0 star property
9.4 out of 10, Exceptional, (6)
"This was quite a charming home. The access to public transportation was great. One mile walk or drive to parking garage. We ventured into the city every day but could have easily stayed in Oak Park."
Historic Oak Park Residence

Lovely 2-Bdrm unit with pool. Home away from home.

8.6 out of 10, Excellent, (20)
"The condo was clean but was needed to be updated. "
Lovely 2-Bdrm unit with pool. Home away from home.

LUXE 3 BR, 2 BA + Hot Tub

8.8 out of 10, Excellent, (15)
"Older property which matched description well. Comfortably fit 5 adults and teens for 4 night stay. Quiet neighborhood even though it is right next to highway. Grocery store within a few mins. We traveled several times to downtown Chicago and Rosemont without issues (other than normal chicago traffic). There are stairs from any entrance, so just be prepared if you have a heavy cooler like we did. :) Could have been a bit cleaner, but that would not stop me from staying again. The host...
The price is AU$715
includes taxes & fees
2 Dec - 3 Dec
LUXE 3 BR, 2 BA + Hot Tub

Oak Park Queen

9.2 out of 10, Wonderful, (9)
"I was mostly confused about how to go about checking in so i had to call. We were told we would get an email soon telling us everything we needed to know which is fine, but we didnt know that till almost check in time. A minor inconvenience but not serious. Loved the area!"
The price is AU$400
includes taxes & fees
1 Dec - 2 Dec
Oak Park Queen

Fox River Retreat

9.8 out of 10, Exceptional, (22)
"Great place and location to stay. After a long day of work it was nice to come back to a quite getaway to relax"
Fox River Retreat

Sunny Coach House in Historic Oak Park

9.8 out of 10, Exceptional, (47)
"Hosts were great place check on easy! Would stay again."
Sunny Coach House in Historic Oak Park

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (162)
"Very clean and well maintained. Would stay again for sure. "
Historic home with easy access to Chicago

Downtown Oak Park/Fast WIFI/Free Parking/ Victorian Home/Sleeps 6

9.4 out of 10, Exceptional, (12)
"This is an amazing location minutes from everything - including the green line to downtown. This is a well maintained, well stocked, comfortable rental in a perfect location. With a very hospitable and communicative host. We would book this again in a minute "
Downtown Oak Park/Fast WIFI/Free Parking/ Victorian Home/Sleeps 6

Comforting Retreat Near Woodfield Mall by RedAwning

9.4 out of 10, Exceptional, (10)
"Nice place to stay, will definitely stay again. "
Comforting Retreat Near Woodfield Mall by RedAwning

Game room+King Bed+WiFi+Near Chicago & O’Hare

10.0 out of 10, Exceptional, (22)
"We had 5 people stay. 3 bedrooms and the two couches that fold out into beds. We hung out on the deck each night, but never ended up using the fire pit. Was a warm night anyway. Great stay. "
The price is AU$675
includes taxes & fees
9 Dec - 10 Dec
Game room+King Bed+WiFi+Near Chicago & O’Hare

Pet-Friendly Bartlett Farmhouse w/ Deck!

9.6 out of 10, Exceptional, (5)
"My mother and aunt LOVED the decor."
Pet-Friendly Bartlett Farmhouse w/ Deck!

Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago

9.2 out of 10, Wonderful, (13)
"Enjoyed our stay, great location, we will stay there again on our next trip to Chicago"
Peaceful 2 Bed w FirePit Free Parking 15 mins to Downtown Chicago

First floor of Historic Oak Park Villa / 2Car Grge

9.6 out of 10, Exceptional, (20)
"Lovely place. Spacious and comfortable. Communication with property manager easy and accommodating. "
The price is AU$736
includes taxes & fees
13 Dec - 14 Dec
First floor of Historic Oak Park Villa / 2Car Grge

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (43)
"Great house in a great locations. Beautiful backyard with ample room and swing set for the kids. The rooms are big with very comfortable beds. Love the house. "
Breathtaking home close to Schaumburg, Chicago

Riverfront rental with fun activities

10.0 out of 10, Exceptional, (22)
"Great place, awesome host. Would definitely recommend. "
The price is AU$341
includes taxes & fees
2 Dec - 3 Dec
Riverfront rental with fun activities

Your Next Vacation Home

9.8 out of 10, Exceptional, (28)
"Thank you for your warm hosting. Everything was great! We’ll come back! "
The price is AU$448
includes taxes & fees
2 Dec - 3 Dec
Your Next Vacation Home

1BR Apartment - Walk to Shops - Downtown OAK PARK

9.2 out of 10, Wonderful, (35)
"Stayed close to home for some construction. Location was perfect, communication with host easy and fast. Access was easy. Needs updated furniture and pillows. "
The price is AU$315
includes taxes & fees
3 Dec - 4 Dec
1BR Apartment - Walk to Shops - Downtown OAK PARK
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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Other types of properties in Winfield you may be interested in

Hilton Chicago O'Hare Airport

4.0 star property
7.8 out of 10, Good, (2097)
"Convenient "
The price is AU$372
includes taxes & fees
27 Nov - 28 Nov
Hilton Chicago O'Hare Airport

Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel

3.0 star property
8.8 out of 10, Excellent, (1559)
"Great location"
The price is AU$188
includes taxes & fees
1 Dec - 2 Dec
Holiday Inn Chicago O'Hare – Rosemont, an IHG Hotel

Marriott Chicago O'Hare

3.5 star property
8.4 out of 10, Very good, (1027)
"Charging for parking is a crime…it’s not downtown Chicago. "
The price is AU$230
includes taxes & fees
14 Dec - 15 Dec
Marriott Chicago O'Hare
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Are there 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. Winfield is known for its shopping and restaurants.

What are some of the best holiday rentals that Winfield has to offer?

3BD/2BA DUAL LEVEL WITH FAMILY ROOM KING BED/LAUNDRY ROOM- IDEAL 4 EXTENDED STAY: This holiday home rental outside of Winfield offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable 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. Kick off your shoes and enjoy yourself with a garden and a selection of games.

How many holiday rentals are there in Winfield?

Choose from 3 Expedia holiday rentals in Winfield for a memorable holiday.

What can I see and do in Winfield?

Cantigny Park and Blackwell Forest Preserve are a couple of lovely local spots to get outside and enjoy nature. In the wider area, you’ll find Royal Golf Club at Klein Creek and Wheaton College.

What’s a holiday rental in Winfield like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winfield. Holiday rentals provide amenities like WiFi and washers and dryers so you'll be comfy for your stay. If you're concerned about a sanitised environment, holiday rentals can provide a sense of seclusion away from public hotel lifts and busy front desks while still allowing you to travel. You'll also find 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 or small group gatherings.