Winfield Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Winfield vacation rentals

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, (9 reviews)
"Very nice little spot... Host was absolutely wonderful!!! Definitely stay here again!"
United States
Adam B.
The price is CA $130
CA $234 total
includes taxes & fees
May 10 - May 11
F.R.I.E.N.D.S inspired studio in beautiful Barrington with WiFi, AC

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

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (23 reviews)
"Easy to access, big place, great for a group that needs to have several rooms and beds. Would definitely stay again"
United States
JOSE S.
The price is CA $203
CA $416 total
includes taxes & fees
May 12 - May 13
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is CA $238
CA $602 total
includes taxes & fees
May 11 - May 12
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (65 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is CA $232
CA $427 total
includes taxes & fees
May 11 - May 12
✽ Charming Cottage ✽ close to College/Town/Station

- Fully-Equipped Condo - King Bed - Massive yard -

- Fully-Equipped Condo - King Bed - Massive yard -
Geneva
10.0 out of 10, Exceptional, (39 reviews)
"We really enjoyed our stay here. The kitchen had everything we needed and the house was very nice. Finding the driveway was a bit tricky in the dark. Thank you for a welcoming place to call home while we were in town for a wedding. "
United States
Cathy
The price is CA $142
CA $365 total
includes taxes & fees
May 11 - May 12
- Fully-Equipped Condo - King Bed - Massive yard -

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, (63 reviews)
"Comfortable bed, spacious rooms and clean."
United States
Michael W.
The price is CA $127
CA $319 total
includes taxes & fees
May 13 - May 14
Chic Suite/Mins to L Train /Laundry/Free Parking

Riverfront rental

Riverfront rental
South Elgin
9.8 out of 10, Exceptional, (39 reviews)
"Luci was excellent. A quiet lovely house on the river. Thank you"
United States
Brian N.
The price is CA $239
CA $337 total
includes taxes & fees
May 11 - May 12
Riverfront rental

Spacious 5-bedroom bungalow in welcoming Berwyn

Spacious 5-bedroom bungalow in welcoming Berwyn
Berwyn
10.0 out of 10, Exceptional, (3 reviews)
"We had an excellent stay. Our host was responsive & accommodated an extremely early check-in request for us. This helped tremendously. Instructions were clear to get in & the home was spacious & clean. The location was great & easily accessible to restaurants. We would stay here again. "
United States
Sarah H.
The price is CA $301
CA $501 total
includes taxes & fees
May 20 - May 21
Spacious 5-bedroom bungalow in welcoming Berwyn

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away
Lockport
10.0 out of 10, Exceptional, (4 reviews)
"Great stay. Nice place. Easy access. Clean. "
United States
Juan S.
The price is CA $148
CA $298 total
includes taxes & fees
May 17 - May 18
King Size Bed, Near Hwy, Work Desk, Parking Just A Few Feet Away

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard
Arlington Heights
9.0 out of 10, Wonderful, (6 reviews)
"Host was very responsive. Location was perfect for what we needed.Really liked having a garage for the car."
United States
Katie C.
The price is CA $240
CA $600 total
includes taxes & fees
May 10 - May 11
PROMO 10% WEEKLY 15% MONTHLY DISCOUNT 2-Car Garage Cal King Bed Fenced Yard

4BR Near Woodfield Mall & Metra | LCP Collection

4BR Near Woodfield Mall & Metra | LCP Collection
Schaumburg
8.4 out of 10, Very good, (5 reviews)
"Home was perfect for us with two kids. Beds were comfortable and a nice quiet location."
United States
Randy G.
The price is CA $312
CA $782 total
includes taxes & fees
May 12 - May 13
4BR Near Woodfield Mall & Metra | LCP Collection

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

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
10.0 out of 10, Exceptional, (12 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is CA $145
CA $184 total
includes taxes & fees
May 20 - May 21
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is CA $288
CA $511 total
includes taxes & fees
May 26 - May 27
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Just remodeled apartment close to airport and mall

Just remodeled apartment close to airport and mall
Elk Grove Village
10.0 out of 10, Exceptional, (16 reviews)
"Very nice place to stay in secure neighborhood "
United States
Christina F.
The price is CA $205
CA $376 total
includes taxes & fees
May 25 - May 26
Just remodeled apartment close to airport and mall

Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Stylish Luxe King bed w/Free Parkng near DT Oak Pk
Oak Park
9.6 out of 10, Exceptional, (99 reviews)
"Everything was good!"
United States
Brio
The price is CA $197
CA $415 total
includes taxes & fees
Jun 2 - Jun 3
Stylish Luxe King bed w/Free Parkng near DT Oak Pk

Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (30 reviews)
"Wonderful place to gather for our annual corporate operations retreat. A great place to disconnect and focus. "
United States
Jennifer A.
The price is CA $271
CA $748 total
includes taxes & fees
May 12 - May 13
Oak Park Victorian by FLW Studio

Modern Condo • Safe Chicago Stay Near O’Hare

Modern Condo • Safe Chicago Stay Near O’Hare
O'Hare
The price is CA $71
CA $374 total
includes taxes & fees
May 11 - May 12
Modern Condo • Safe Chicago Stay Near O’Hare

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking
Bensenville
10.0 out of 10, Exceptional, (1 review)
"Easily the nicest place I have ever stayed at. Wonderful neighborhood, clean house, and great amenities. I’ll stay there again anyday. "
United States
Jacob F.
The price is CA $254
CA $801 total
includes taxes & fees
May 11 - May 12
Luxury 4BR, 3BA, Game Rm Near O’Hare & Down Town Free Parking

- Beautiful Condo - King Bed - Free Waffle Breakfast -

- Beautiful Condo - King Bed - Free Waffle Breakfast -
Geneva
10.0 out of 10, Exceptional, (26 reviews)
"We had a lovely stay! The property was well appointed and comfortable. The host was very responsive. "
United States
Kathryn M.
The price is CA $166
CA $396 total
includes taxes & fees
May 10 - May 11
- Beautiful Condo - King Bed - Free Waffle Breakfast -

Cozy, Comfortable and Convenient apartment. Close to everything!

Cozy, Comfortable and Convenient apartment. Close to everything!
Oak Park
9.8 out of 10, Exceptional, (74 reviews)
"Nice, clean, safe house."
United States
Adrienne P.
The price is CA $197
CA $471 total
includes taxes & fees
May 20 - May 21
Cozy, Comfortable and Convenient apartment. Close to everything!
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Winfield Hotel Reviews

Find out more about Winfield

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Winfield. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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?

LUXE 3 BR, 2 BA + Hot Tub: Visitors like this Winfield vacation home rental. It is equipped with a patio, air-conditioning, and laundry facilities to help you feel comfortable during your stay.

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 Addison Ice Arena, 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.