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Winnetka Holiday Rentals

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Our top choices for Winnetka holiday rentals

Master qtr close to nature & easy urban facilities

Master qtr close to nature & easy urban facilities
Riverwoods
9.8 out of 10, Exceptional, (84 reviews)
"nice little place! quiet area "
United States
Nayeli A.
The price is AU$297
includes taxes & fees
28 June - 29 June
Master qtr close to nature & easy urban facilities

3BR Luxury Suite w/Gym and Balcony

3BR Luxury Suite w/Gym and Balcony
Downtown Chicago
9.4 out of 10, Exceptional, (30 reviews)
"A wonderful place to stay and everything was so perfect! Could not recommend staying here enough! "
United States
Cassidy L.
The price is AU$1,075
includes taxes & fees
1 July - 2 July
3BR Luxury Suite w/Gym and Balcony

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley
North Center
9.6 out of 10, Exceptional, (81 reviews)
"Great location for a short trip "
United States
Eric W.
The price is AU$511
includes taxes & fees
21 June - 22 June
Explore Chicago: Stylish 2BR, 1 Block to El Train & Close to Wrigley

River North Rooftop With In and Out Parking 5

River North Rooftop With In and Out Parking 5
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"Everything was amazing, property was even better than expected"
United States
Jacob
The price is AU$801
includes taxes & fees
9 July - 10 July
River North Rooftop With In and Out Parking 5

Modern West Loop Gem-City Views & Prime Location 5

Modern West Loop Gem-City Views & Prime Location 5
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"Great stay."
United States
Mollie A.
The price is AU$857
includes taxes & fees
7 July - 8 July
Modern West Loop Gem-City Views & Prime Location 5

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (5 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is AU$846
includes taxes & fees
1 July - 2 July
River North Rooftop With In and Out Parking 3

Cozy studio in Andersonville Chicago

Cozy studio in Andersonville Chicago
Edgewater
9.6 out of 10, Exceptional, (83 reviews)
"Great stay i loved it"
United States
Cedes W.
The price is AU$304
includes taxes & fees
5 July - 6 July
Cozy studio in Andersonville Chicago

Premium Urban 4BR - Perfect Mix of Comfort & Location

Premium Urban 4BR - Perfect Mix of Comfort & Location
Near North Side
10.0 out of 10, Exceptional, (1 review)
"Nice place, clean property, great views "
United States
Zach L.
The price is AU$1,413
includes taxes & fees
9 July - 10 July
Premium Urban 4BR - Perfect Mix of Comfort & Location

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More
South Evanston
10.0 out of 10, Exceptional, (49 reviews)
"The place was awesome - very clean !! Great location !! "
United States
John R.
The price is AU$385
includes taxes & fees
7 July - 8 July
Cozy Neighborhood Escape: Near Northwestern-Chicago-Beaches & More

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, (64 reviews)
"This was a very cute apartment in a really nice neighborhood! We got a little confused about check-in because the parking space and the lockbox are not clearly marked. A couple of big, comfy couches in the living room would have made it a little more comfortable for 2 adults and 2 tall teenagers. Otherwise it was perfect and we would definitely stay again."
United States
Erin
Chic Suite/Mins to L Train /Laundry/Free Parking

LIVN West Loop Chicago Queen Superior Studio

LIVN West Loop Chicago Queen Superior Studio
Downtown Chicago
10.0 out of 10, Exceptional, (7 reviews)
"The service was top notch at this property. The hosts were super responsive and professional. The location was incredible. Loved being able to cook in the apartment. The apartment was newly renovated and very urban chic. "
United States
Michelle R.
The price is AU$350
includes taxes & fees
21 June - 22 June
LIVN West Loop Chicago Queen Superior Studio

Cozy 1BR in Walkable Area

Cozy 1BR in Walkable Area
Lincoln Square
9.8 out of 10, Exceptional, (15 reviews)
"The apartment was very clean and the host was very helpful!"
United States
Avery
The price is AU$345
includes taxes & fees
7 July - 8 July
Cozy 1BR in Walkable Area

Trendy & Comfy Studio Unit

Trendy & Comfy Studio Unit
Portage Park
9.4 out of 10, Exceptional, (8 reviews)
"Nice clean space"
United States
Griffin
The price is AU$284
includes taxes & fees
30 June - 1 July
Trendy & Comfy Studio Unit

Quaint Bungalow, near Great Lakes Naval Base

Quaint Bungalow, near Great Lakes Naval Base
Mundelein
9.8 out of 10, Exceptional, (72 reviews)
"We had a great stay! The area was peaceful and felt safe. "
United States
Yoselin V.
The price is AU$496
includes taxes & fees
5 July - 6 July
Quaint Bungalow, near Great Lakes Naval Base

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
8.8 out of 10, Excellent, (3 reviews)
The price is AU$382
includes taxes & fees
22 June - 23 June
1BR Modern Luxe Apt with In-Unit Laundry

Vibrant 1BR Apartment

Vibrant 1BR Apartment
Lakeview
9.6 out of 10, Exceptional, (8 reviews)
"Great place. Host was very informative. "
United States
Cheryl S.
The price is AU$337
includes taxes & fees
22 June - 23 June
Vibrant 1BR Apartment

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

Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking
Northlake
9.8 out of 10, Exceptional, (15 reviews)
"Had a great experience here, and also close to the airport!"
United States
Yafeat D.
The price is AU$260
includes taxes & fees
21 June - 22 June
Cozy Garden Suite minutes from O'hare and Rosemont + Free Parking

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago Stay with Free In & Out Parking 5
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
The price is AU$793
includes taxes & fees
7 July - 8 July
Downtown Chicago Stay with Free In & Out Parking 5

Sunlit Studio with City Charm

Sunlit Studio with City Charm
Rogers Park
8.4 out of 10, Very good, (14 reviews)
"Host was extremely welcoming and accommodating. They went out of their way to assure me that they were but a call away if there was anything we needed."
United States
Renee W.
The price is AU$295
includes taxes & fees
24 June - 25 June
Sunlit Studio with City Charm
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$273 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?

ENVITAE Hotel, 4BR Luxury Modern Apartments: This holiday home rental outside of Winnetka is located in the city centre, and offers a BBQ, air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.