Winfield Holiday Rentals

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Holiday Rentals in Winfield

Our top choices for Winfield holiday rentals

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

8.0 out of 10, Very good, (7)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
The price is AU$376
includes taxes & fees
8 Sept - 9 Sept
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Zoo Holiday Retreat beautiful home with parking, near train into Chicago.

10.0 out of 10, Exceptional, (2)
"Excellent location, right by the zoo, the place is well stocked and clean, in a nice neighborhood. Close to attractions and easy to go to other western suburbs of Chicago. Has everything we needed :). The host was great with communicating and was able to allow us to borrow a pack n play as well. Would stay again! "
The price is AU$929
includes taxes & fees
2 Sept - 3 Sept
Zoo Holiday Retreat beautiful home with parking, near train into Chicago.

4BR Retreat w/ Theater, Game Room & Backyard

8.0 out of 10, Very good, (8)
The price is AU$777
includes taxes & fees
23 Sept - 24 Sept
4BR Retreat w/ Theater, Game Room & Backyard

Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

8.0 out of 10, Very good, (3)
"Only complaint was the fact that the yard was not cut and the grass needed to maintained"
The price is AU$718
includes taxes & fees
23 Sept - 24 Sept
Rumble In the Jungle Charming 3-bedroom house in nice Addison with AC, WiFi

Less is more! Pet friendly Tiny Home near Chicago!

9.8 out of 10, Exceptional, (24)
"Could not have picked a better place to stay. Location was grea,fenced in area fir the dogs was perfecy. "
The price is AU$263
includes taxes & fees
2 Sept - 3 Sept
Less is more! Pet friendly Tiny Home near Chicago!

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

9.6 out of 10, Exceptional, (25)
"We loved the location! It was perfect for us. Denise was very pleasant. We will definitely stay there again."
The price is AU$168
includes taxes & fees
2 Sept - 3 Sept
Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum

Oak Park Queen

8.4 out of 10, Very good, (28)
"This was a great place to stay! "
The price is AU$363
includes taxes & fees
3 Sept - 4 Sept
Oak Park Queen

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (21)
"Comfortable beds and room for everyone. Nice quiet neighborhood and a great home away from home. Would stay there again. Host was very easy to work with and responded quickly to questions. "
Cozy 3-bedroom house in family-oriented Melrose Park.

✽ Charming Cottage ✽ close to College/Town/Station

10.0 out of 10, Exceptional, (47)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
The price is AU$486
includes taxes & fees
4 Sept - 5 Sept
✽ Charming Cottage ✽ close to College/Town/Station

Breathtaking home close to Schaumburg, Chicago

9.8 out of 10, Exceptional, (66)
"Fit our whole family nicely."
Breathtaking home close to Schaumburg, Chicago

Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

10.0 out of 10, Exceptional, (105)
"We had an amazing stay at Jamie’s place. Quiet location, great host, and lovely accommodations. If you’re visiting Chicago, highly recommend staying at Jamie’s. "
Cozy Comfy Clean 420 Compliant FREE Parking QUIET Neighborhood A GUEST FAVORITE!

3BR Oasis, Gym, Workspace, Quiet Location

2.0 star property
10.0 out of 10, Exceptional, (1)
"Convenient, beautiful, and clean stay! We would stay again"
3BR Oasis, Gym, Workspace, Quiet Location

Des Plaines Vacation Rental w/ Spacious Backyard!

9.0 out of 10, Wonderful, (16)
"Easy access good parking clean well stocked but very small three bedroom house with nice outdoor sitting and eating area near Rosemont"
Des Plaines Vacation Rental w/ Spacious Backyard!

Enamored in Elmhurst

2.0 star property
10.0 out of 10, Exceptional, (12)
"Great stay"
The price is AU$767
includes taxes & fees
2 Sept - 3 Sept
Enamored in Elmhurst

Clarendon Hills Top Floor

6.8 out of 10, (10)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor

New Modern 3BR, Gym, Workspace, Quiet Location

2.0 star property
8.0 out of 10, Very good, (2)
"Great time, clean and lovely place in a quiet area!"
New Modern 3BR, Gym, Workspace, Quiet Location

Comfy 2-bedroom apartment with AC, WiFi in Oak Park

10.0 out of 10, Exceptional, (1)
"Very responsive, parking and nice layout "
Comfy 2-bedroom apartment with AC, WiFi in Oak Park

2BR <10mins O’Hare &Transit Newly Furnished Modern

7.4 out of 10, Good, (3)
"Great place! Nice, safe neighborhood. The host was very helpful. "
The price is AU$553
includes taxes & fees
2 Sept - 3 Sept
2BR <10mins O’Hare &Transit Newly Furnished Modern

V1 Private Room In Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation

2.0 out of 10, (1)
"Horrible"
The price is AU$234
includes taxes & fees
31 Aug - 1 Sept
V1 Private Room In Naperville Downtown with Wi-fi Desk, Near HighwayTrainStation

Chicago-burb -Medinah -1 King and 1 Queen beds

9.4 out of 10, Exceptional, (27)
"The property was very clean and comfortable!"
Chicago-burb -Medinah -1 King and 1 Queen beds
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

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 favourite 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 depend 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 AU$168 per night. Entering your travel dates in the search wizard might find you 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 Addison Ice Arena, 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.