Winnetka Holiday Rentals

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Holiday Rentals in Winnetka

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (966)
"Loved my stay! Staff was amazing and the apartment had everything to make you feel like home. "
United States
Nicole
The price is AU$284
includes taxes & fees
11 Nov - 12 Nov
Sentral Michigan Avenue
Level Chicago – Old Town
4.0 star property
9.0 out of 10, Wonderful, (373)
"Easy check-in, friendly staff, beautiful building with nice amenities. "
United States
Matthew
The price is AU$400
includes taxes & fees
11 Nov - 12 Nov
Level Chicago – Old Town
Kasa River North Chicago
4.0 star property
9.6 out of 10, Exceptional, (174)
"Awesome stay "
United States
Sally
Kasa River North Chicago
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
3.5 star property
8.2 out of 10, Very good, (185)
"Place was amazing! Very centralized, all sorts of restaurants nearby, and right next to the CTA Trains which is AWESOME!"
United States
Alexander
The price is AU$196
includes taxes & fees
24 Nov - 25 Nov
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park
Cozy Gold Coast Studio Stay
10.0 out of 10, Exceptional, (2)
"The communication was really effective and made for a smooth check in and check out process. Host was friendly and made great recommendations, 10/10 would stay again!"
United States
Seynabou
The price is AU$306
includes taxes & fees
2 Nov - 3 Nov
Cozy Gold Coast Studio Stay
Your Chicago get Away
8.4 out of 10, Very good, (8)
"Clean, fun space and responsive host! Loved the views from our room!"
United States
Tyler C.
Your Chicago get Away
Twice as Nice: Chic 2BR Stay with Style & Space
9.4 out of 10, Exceptional, (10)
"Had a very nice time in Chicago!"
United States
Valerie S.
The price is AU$365
includes taxes & fees
11 Nov - 12 Nov
Twice as Nice: Chic 2BR Stay with Style & Space
Stylish 1BR in West Loop
10.0 out of 10, Exceptional, (7)
"We stayed for 4th of July weekend and had a wonderful time. Property is close to coffee shops, book stores, and within walking distance of nice restaurants. Easy paid parking nearby. The apartment was clean and everything we needed"
United States
Jacob D.
The price is AU$324
includes taxes & fees
11 Nov - 12 Nov
Stylish 1BR in West Loop
4BR Corporate Suite Central and Modern
2.0 star property
10.0 out of 10, Exceptional, (6)
"We loved at our stay at this property. It was one of the best stays we have had on vacation."
United States
Javeria
4BR Corporate Suite Central and Modern
Sun-Drenched 1BR Apartment
10.0 out of 10, Exceptional, (1)
"The location was fantastic. We were just a couple blocks from the Green and Pink line on Clinton. There was a code to get into the building so it felt safe. The code to the door was great because there was no key to worry about since I had to work and my hubby was in and out of the apartment all day. There were a couple small things, the bed squeaks a lot. Also, it is very clear in the listing that the train is close. It is about 30ft straight out from the window. I'm not a light sleeper so I...
United States
Jennifer A.
The price is AU$324
includes taxes & fees
11 Nov - 12 Nov
Sun-Drenched 1BR Apartment
The One: A 1BR Stay That Feels Like Home
9.0 out of 10, Wonderful, (2)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is AU$317
includes taxes & fees
2 Nov - 3 Nov
The One: A 1BR Stay That Feels Like Home
South Loop Rooftop With In and Out Parking 2
The price is AU$479
includes taxes & fees
17 Nov - 18 Nov
South Loop Rooftop With In and Out Parking 2
Chicago Third Floor Studio by 747 Lofts
2.0 star property
9.6 out of 10, Exceptional, (5)
"Cute little studio that was clean. There was a nice size kitchen and was close to our activities in the West loop of Chicago. There was also assistance with parking located in the lofts."
United States
Jennifer
The price is AU$346
includes taxes & fees
5 Nov - 6 Nov
Chicago Third Floor Studio by 747 Lofts
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
3.5 star property
8.0 out of 10, Very good, (394)
"Great location. Was there for the marathon and had a great stay. "
United States
HELGA
The price is AU$180
includes taxes & fees
11 Nov - 12 Nov
Sonder by Marriott Bonvoy Market Hall Apartments West Loop
West Loop Living – Bright 1BR
The price is AU$324
includes taxes & fees
11 Nov - 12 Nov
West Loop Living – Bright 1BR
1BR Modern Luxe Apt with In-Unit Laundry
The price is AU$324
includes taxes & fees
11 Nov - 12 Nov
1BR Modern Luxe Apt with In-Unit Laundry
Spacious 3-bedroom apartment near downtown, FREE PARKING
9.4 out of 10, Exceptional, (8)
"Nice place to stay. Good communication with the owner."
United States
Ryan
The price is AU$519
includes taxes & fees
3 Nov - 4 Nov
Spacious 3-bedroom apartment near downtown, FREE PARKING
Premium Urban 4BR - Perfect Mix of Comfort & Location
10.0 out of 10, Exceptional, (1)
"Nice place, clean property, great views "
United States
Zach L.
Premium Urban 4BR - Perfect Mix of Comfort & Location
A quiet stay while you are away
9.8 out of 10, Exceptional, (32)
"We stayed a few nights and everything was nice and clean. Thank you!"
United States
Karigan H.
The price is AU$312
includes taxes & fees
24 Nov - 25 Nov
A quiet stay while you are away
Chicago luxury home suites
2.0 star property
The price is AU$1,739
includes taxes & fees
11 Nov - 12 Nov
Chicago luxury home suites
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 Winnetka Hotel Reviews

Find out more about Winnetka

Everything you need to know about Winnetka 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 Winnetka 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 Winnetka holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Winnetka holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Winnetka. 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 Winnetka 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 Winnetka holiday rentals we have selected for you start as low as AU$180 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Winnetka rentals

At Expedia, we put the best Winnetka 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 Winnetka 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 Winnetka 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 Winnetka. 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

Can I find holiday rentals in Winnetka?

Yes, there are holiday rentals in Winnetka close to Chocolate Box, or you can select a more secluded option if you're looking for a relaxing stay. Winnetka is known for its shopping and forests. Make sure you have time to check out the sporting events and restaurants during your trip.

What are some of the best holiday rentals that Winnetka has to offer?

Wrigley Field/Lakeview -Entire Home- Large Groups!: This holiday home rental outside of Winnetka is located on a lake, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of games.

What can I see and do in Winnetka?

Lake Michigan and Maple Street Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Chocolate Box. While in the area, you can also visit popular places such as Wrigley Field and Naval Base Great Lakes.

What are holiday rentals like in Winnetka?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Winnetka. Holiday rentals offer extras like laundry facilities and kitchens so you'll have everything you need. If you're concerned about a clean environment, a holiday rental can provide a sense of safety away from shared hotel lifts and bustling concierge desks while still allowing you to travel. You'll also get more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for a family trip or a small group gathering.