Winfield Vacation Rentals

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Our top choices for Winfield vacation rentals

2.0 star property
$180 nightly
The price is $206
Dec 29 - Dec 30
Total with taxes and fees
Explore Chicago! / King Bd near Train / Near Shops
9.6 out of 10, Exceptional, (30)
"Great option for a relatively affordable place to stay near family."
United States
Erick B.
$99 nightly
The price is $105
Jan 19 - Jan 20, 2026
Total with taxes and fees
Pet Friendly-Cozy 1-bedroom apartment just 6 minutes drive to Morton Arboretum
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.
$257 nightly
The price is $294
Dec 27 - Dec 28
Total with taxes and fees
Cozy, Comfortable and Convenient apartment. Close to everything!
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.
$169 nightly
The price is $194
Jan 5 - Jan 6, 2026
Total with taxes and fees
Chic Suite/Mins to L Train /Laundry/Free Parking

Apartment in Chicago

3BR Sunny & Cozy Unit
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.
$197 nightly
The price is $211
Dec 29 - Dec 30
Total with taxes and fees
3BR Sunny & Cozy Unit
10.0 out of 10, Exceptional, (2)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
$115 nightly
The price is $123
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
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.
$182 nightly
The price is $208
Dec 30 - Dec 31
Total with taxes and fees
Restful Comfy Retreat W Free Parking with Laundry and Close to Downtown Chicago
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.
$197 nightly
The price is $211
Dec 27 - Dec 28
Total with taxes and fees
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC
3.0 star property
$387 nightly
The price is $412
Jan 1 - Jan 2, 2026
Total with taxes and fees
Classic Forest Park Foursquare < 1 Mi to Blue Line

Vacation Home in La Grange Highlands

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
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.
$270 nightly
The price is $289
Dec 30 - Dec 31
Total with taxes and fees
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
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.
$180 nightly
The price is $193
Dec 29 - Dec 30
Total with taxes and fees
Chicago style apt/Near Hosp/ORD/MDW/DT
2.0 star property
$299 nightly
The price is $353
Jan 14 - Jan 15, 2026
Total with taxes and fees
2BR • Newly Furnished Modern Apt • Near O'Hare
2.0 star property
$244 nightly
The price is $297
Jan 1 - Jan 2, 2026
Total with taxes and fees
Near O'hare • Personal Gym and Balcony • Safe Area

Apartment in Arlington Heights

Sunny 1BR Apartment in the Surburbs
7.4 out of 10, Good, (6)
"Clean, quiet neighborhood. Apartment as pictured."
United States
Terri A.
$150 nightly
The price is $162
Dec 28 - Dec 29
Total with taxes and fees
Sunny 1BR Apartment in the Surburbs
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.
$241 nightly
The price is $255
Jan 20 - Jan 21, 2026
Total with taxes and fees
Keyless, KING bd, WIFI, desk, Fox River Bike Trail, near MetraTrain
2.0 star property
$256 nightly
The price is $303
Dec 31 - Jan 1, 2026
Total with taxes and fees
Modern Condo • Safe Chicago Stay Near O’Hare
$382 nightly
The price is $437
Dec 28 - Dec 29
Total with taxes and fees
Charming 2-bedroom apartment with AC, WiFi in delightful Oak Park

Apartment in Arlington Heights

Chic 1BR Apt -Arlington Heights
$150 nightly
The price is $162
Dec 29 - Dec 30
Total with taxes and fees
Chic 1BR Apt -Arlington Heights
9.6 out of 10, Exceptional, (8)
"Very romantic getaway and me and my girlfriend felt like we belonged there! "
United States
Zachary G.
$282 nightly
The price is $299
Jan 1 - Jan 2, 2026
Total with taxes and fees
Cozy 2 bd/1ba upper apt -Free WIFI, parking -1mi to Geneva 3rd & Chicago Metra

Apartment in Oak Park

Oak Park Queen
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.
$197 nightly
The price is $226
Jan 4 - Jan 5, 2026
Total with taxes and fees
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 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 $105 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.

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.