Winfield Vacation Rentals

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Check prices for these dates

In two weeks
Jan 2 - Jan 4
In two months
Feb 13 - Feb 15
In three months
Mar 13 - Mar 15
In four months
Apr 10 - Apr 12

Our top choices for Winfield vacation rentals

Smart TV
Getaway Near ORD With Great Local Amenities

Getaway Near ORD With Great Local Amenities

Getaway Near ORD With Great Local Amenities
Des Plaines
9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
The price is ￥10,992
￥43,567 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Getaway Near ORD With Great Local Amenities
Microwave, oven, stovetop
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
2.0 star property
Northlake
10.0 out of 10, Exceptional, (2)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is ￥11,989
￥16,201 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Property grounds
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Downers Grove
9.6 out of 10, Exceptional, (30)
"Great option for a relatively affordable place to stay near family."
United States
Erick B.
The price is ￥9,465
￥17,554 total
includes taxes & fees
Jan 19 - Jan 20, 2026
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
Fridge, microwave, oven, stovetop
3BR Sunny & Cozy Unit

3BR Sunny & Cozy Unit

3BR Sunny & Cozy Unit
Chicago
8.4 out of 10, Very Good, (5)
"Great location! Few minute walk to Lake Michigan. Very convenient. We absolutely enjoyed our stay!"
United States
le f.
The price is ￥11,674
￥33,331 total
includes taxes & fees
Dec 22 - Dec 23
3BR Sunny & Cozy Unit
Fridge, microwave, oven, stovetop
Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport

Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport

Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport
2.0 star property
Stickney
The price is ￥10,412
￥38,815 total
includes taxes & fees
Dec 22 - Dec 23
Stylish 2-Bedroom Condo – Easy Drive to Downtown Chicago & Midway Airport
TV, offices
Curated for Cozy Stays -2 Parking Spaces, Sleeps 4

Curated for Cozy Stays -2 Parking Spaces, Sleeps 4

Curated for Cozy Stays -2 Parking Spaces, Sleeps 4
Westmont
8.4 out of 10, Very Good, (5)
"Great experience and great location very grateful for the stay, would highly recommend."
United States
DeMarco L.
The price is ￥14,671
￥50,660 total
includes taxes & fees
Dec 22 - Dec 23
Curated for Cozy Stays -2 Parking Spaces, Sleeps 4
Fridge, microwave, oven, stovetop
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
Oak Park
8.8 out of 10, Excellent, (25)
"Property was great.. super cute space and the neighborhood was great, felt very safe and no problems. "
United States
Nadar A.
The price is ￥11,358
￥33,230 total
includes taxes & fees
Dec 30 - Dec 31
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
House (3 Bedrooms) | Interior
Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
3.0 star property
Forest Park
The price is ￥24,925
￥65,071 total
includes taxes & fees
Dec 22 - Dec 23
Classic Forest Park Foursquare < 1 Mi to Blue Line
Fridge, microwave, oven, stovetop
Chic Suite/Mins to L Train /Laundry/Free Parking

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

Chic Suite/Mins to L Train /Laundry/Free Parking
Oak Park
9.6 out of 10, Exceptional, (57)
"Super convenient if you want to see the Frank Lloyd wright house - walked to studio and train and great cafes. Perfect location "
United States
Travis S.
The price is ￥10,733
￥31,250 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Chic Suite/Mins to L Train /Laundry/Free Parking
Smart TV
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Barrington
9.8 out of 10, Exceptional, (6)
"Our experience at this place was unique; the best relaxing get away I have had in many years. From check-in to total comfort and cleanliness to privacy and coziness. And “Friends-Themed”accents made our stay specially touching. It was a delight walking downtown to great restaurants and stores while admiring beautifully maintained new and old architectural gems that made us feel both amazed and nostalgic. And more than anything, a town we felt safe and welcomed everywhere. It is for sure one of...
United States
Sarah S.
The price is ￥19,877
￥33,246 total
includes taxes & fees
Dec 26 - Dec 27
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
Smart TV, books
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
Geneva
9.4 out of 10, Exceptional, (32)
"We had a great stay in Geneva for the night. Our spot was very convenient to lots of places around town. I would definitely recommend staying at this location! "
United States
jennifer f.
The price is ￥13,409
￥40,627 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
TV
2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare

2BR • Newly Furnished Modern Apt • Near O'Hare
2.0 star property
O'Hare
The price is ￥10,885
￥55,353 total
includes taxes & fees
Jan 14 - Jan 15, 2026
2BR • Newly Furnished Modern Apt • Near O'Hare
Dining
Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (70)
"My husband, daughter and I went to Chicago for a weekend getaway and this place was clean, cute and so close to transit. Great place for a small family to stay. "
United States
Amy A.
The price is ￥17,037
￥46,773 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cozy, Comfortable and Convenient apartment. Close to everything!
Fridge, microwave, oven, stovetop
Chic 1BR Apt -Arlington Heights

Chic 1BR Apt -Arlington Heights

Chic 1BR Apt -Arlington Heights
Arlington Heights
The price is ￥9,465
￥25,505 total
includes taxes & fees
Dec 28 - Dec 29
Chic 1BR Apt -Arlington Heights
Dining
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
2.0 star property
Oak Park
The price is ￥24,562
￥82,658 total
includes taxes & fees
Dec 22 - Dec 23
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park
Interior
Less is more! Pet friendly Tiny Home near Chicago!

Less is more! Pet friendly Tiny Home near Chicago!

Less is more! Pet friendly Tiny Home near Chicago!
Burr Ridge
9.8 out of 10, Exceptional, (35)
"We loved it!!! Perfect space for the 3 of us area is beautiful!! "
United States
Aaliyah G.
The price is ￥16,327
￥33,500 total
includes taxes & fees
Dec 30 - Dec 31
Less is more! Pet friendly Tiny Home near Chicago!
Fridge, microwave, oven, stovetop
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Geneva
9.6 out of 10, Exceptional, (8)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
The price is ￥19,719
￥47,145 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra
Interior
Spacious, lovely 2bed 1bath with free parking

Spacious, lovely 2bed 1bath with free parking

Spacious, lovely 2bed 1bath with free parking
Oak Park
9.8 out of 10, Exceptional, (18)
"It was a very lovely place to stay. Very clean and inviting."
United States
Kay N.
The price is ￥17,463
￥47,442 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Spacious, lovely 2bed 1bath with free parking
House (3 Bedrooms) | Interior
Fire Pit & Grill: Family Home on Fox River Trail!

Fire Pit & Grill: Family Home on Fox River Trail!

Fire Pit & Grill: Family Home on Fox River Trail!
3.0 star property
St. Charles
The price is ￥28,868
￥85,287 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Fire Pit & Grill: Family Home on Fox River Trail!
Private kitchen
LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
United States
Scott C.
The price is ￥17,037
￥44,383 total
includes taxes & fees
Dec 22 - Dec 23
LUXE 3 BR, 2 BA + 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

Hyatt Regency O'Hare Chicago

Hyatt Regency O'Hare Chicago

10/10 Excellent
"Breakfast was amazing, air conditioning was perfect, the room was so clean and perfect!"
Blessing 2-night trip
Posted 4 days ago
Hyatt Regency O'Hare Chicago

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
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  • 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

Are there vacation rentals in Winfield?

Yes, we give you a choice of vacation rentals close to well known points of interest in Winfield, or you can choose a secluded option if you'd like a relaxing place to stay. Winfield is known for its shopping and restaurants.

What are some of the best vacation rentals in Winfield?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: Visitors like this Winfield vacation home rental. It offers a patio, a barbecue grill, and air-conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop, and a microwave.

How many vacation rentals are there in Winfield?

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

What can I see and do in Winfield?

While exploring the area, visit family-friendly sights like Funway Ultimate Entertainment Center, or get outside and enjoy nature at Blackwell Forest Preserve. In the larger area, you’ll find Royal Golf Club at Klein Creek and Cantigny Golf Club.

What’s a vacation rental in Winfield like?

Vacation rentals are privately owned accommodations you can book for a few days or a quick weekend in Winfield. Vacation rentals feature extras like kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive option for a family getaway.