Winfield Holiday Rentals

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Our top choices for Winfield holiday rentals

Explore Chicago! / King Bd near Train / Near Shops

Explore Chicago! / King Bd near Train / Near Shops
2.0 star property
Oak Park
Explore Chicago! / King Bd near Train / Near Shops

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 NZ$191
includes taxes & fees
19 Jan - 20 Jan 2026
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

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 NZ$504
includes taxes & fees
27 Dec - 28 Dec
Cozy, Comfortable and Convenient apartment. Close to everything!

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 NZ$332
includes taxes & fees
5 Jan - 6 Jan 2026
Chic Suite/Mins to L Train /Laundry/Free Parking

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 NZ$362
includes taxes & fees
29 Dec - 30 Dec
3BR Sunny & Cozy Unit

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 NZ$211
includes taxes & fees
3 Jan - 4 Jan 2026
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

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)
"The house was very comfortable and clean. We definitely enjoyed our stay there, and will keep it in mind next time we visit the area."
United States
Jill S.
The price is NZ$361
includes taxes & fees
4 Jan - 5 Jan 2026
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago

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, (7)
"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 NZ$361
includes taxes & fees
28 Dec - 29 Dec
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

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 NZ$706
includes taxes & fees
4 Jan - 5 Jan 2026
Classic Forest Park Foursquare < 1 Mi to Blue Line

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
La Grange Highlands
10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
The price is NZ$495
includes taxes & fees
30 Dec - 31 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Chicago style apt/Near Hosp/ORD/MDW/DT

Chicago style apt/Near Hosp/ORD/MDW/DT
Berwyn
8.0 out of 10, Very good, (3)
"I stayed with my son who had a basketball tournament around the corner at the Wintrust Sports Complex. The building was nice and furnished well. It was also very homey and comfortable. It was nice having friendly people around the corner and we also enjoyed some mornings with coffee at the Pink Owl Cafe. Overall, everything about this trip was great. We felt safe, comfortable, and at home when we stayed and I look forward to using this property again next year. "
United States
Ace W.
Chicago style apt/Near Hosp/ORD/MDW/DT

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

2BR • Newly Furnished Modern Apt • Near O'Hare
2.0 star property
O'Hare
2BR • Newly Furnished Modern Apt • Near O'Hare

Near O'hare • Personal Gym and Balcony • Safe Area

Near O'hare • Personal Gym and Balcony • Safe Area
2.0 star property
O'Hare
Near O'hare • Personal Gym and Balcony • Safe Area

Sunny 1BR Apartment in the Surburbs

Sunny 1BR Apartment in the Surburbs
Arlington Heights
7.4 out of 10, Good, (6)
"Clean, quiet neighborhood. Apartment as pictured."
United States
Terri A.
The price is NZ$277
includes taxes & fees
28 Dec - 29 Dec
Sunny 1BR Apartment in the Surburbs

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 NZ$437
includes taxes & fees
20 Jan - 21 Jan 2026
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain

Modern Condo • Safe Chicago Stay Near O’Hare

Modern Condo • Safe Chicago Stay Near O’Hare
2.0 star property
O'Hare
Modern Condo • Safe Chicago Stay Near O’Hare

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 NZ$748
includes taxes & fees
29 Dec - 30 Dec
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

Chic 1BR Apt -Arlington Heights

Chic 1BR Apt -Arlington Heights
Arlington Heights
The price is NZ$277
includes taxes & fees
29 Dec - 30 Dec
Chic 1BR Apt -Arlington Heights

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 NZ$512
includes taxes & fees
1 Jan - 2 Jan 2026
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Oak Park Queen

Oak Park Queen
Oak Park
8.2 out of 10, Very good, (31)
"The property was very clean and comfortable. Good location. The owner was responsive."
United States
Susan S.
The price is NZ$383
includes taxes & fees
8 Jan - 9 Jan 2026
Oak Park Queen
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

Find out more about Winfield

Everything you need to know about Winfield holiday rentals

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

Winfield holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Winfield holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Winfield holiday rentals we have selected for you start as low as NZ$191 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Winfield rentals

At Expedia, we put the best Winfield holiday 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 holiday.

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. 

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?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Winfield offers a patio, a BBQ 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 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?

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 wider area, you’ll find Royal Golf Club at Klein Creek and Cantigny Golf Club.

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.