Winnetka Holiday Rentals from €180: Search Short-Term Rentals

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

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line : This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease 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.

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Our top choices for Winnetka holiday rentals

Sentral Michigan Avenue

Downtown Chicago

JAVIER

includes taxes & fees

5 Jul - 6 Jul

Downtown Chicago Stay with Free In & Out Parking 5

Downtown Chicago

Gina C.

LIVN Millennium Park Downtown Chicago Studio

Downtown Chicago

Georgina E.

includes taxes & fees

30 Jun - 1 Jul

South Loop Rooftop With In and Out Parking 2

Downtown Chicago

Kara V.

includes taxes & fees

21 Jul - 22 Jul

River North Rooftop With In and Out Parking 3

Downtown Chicago

Jennifer M.

includes taxes & fees

1 Jul - 2 Jul

River North Rooftop With In and Out Parking 6

Downtown Chicago

Amy L.

includes taxes & fees

19 Jul - 20 Jul

Full-sized fridge, microwave, oven, stovetop

Level Chicago – Old Town

Downtown Chicago

Kimberly

includes taxes & fees

30 Jun - 1 Jul

Beautiful Unit CHI in Prime River North - 1

Downtown Chicago

Robert L.

includes taxes & fees

3 Jul - 4 Jul

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Top Winnetka Hotel Reviews

Omni Chicago Hotel

10/10 Excellent

"The staff were very helpful and kind, room clean and a beautiful view. Hotel kept up very well. Our air conditioning worked great on the 23rd floor. Check out, bags held and valet parking plus retrieval very quick and excellent service."

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"The location and decor in the lobby and restaurant/ lounge was super nice! The beds were comfortable and room was spacious. The only issue that I saw was the carpet in the room. There were several stains and bleach spots. It needs to be replaced. Other than that small detail it was a really nice stay!"

Hotel Riu Plaza Chicago

8/10 Good

"RIU is a beautiful and modern hotel with very helpful staff and an excellent breakfast buffet. The rooms were clean and pretty. Our only concerns were these: The only restaurant on the property is a rooftop bar with small plates that are not kid friendly, and because it’s a rooftop bar, it’s only available when the weather is good. Our shower did not drain. There is no ice machine or any other vending on the property. There is no sundries shop/store on the property. The room does not have a microwave. Our bathroom door did not lock nor, was there any bathroom vent/fan. For being only two years old, the hotel really should have better television options, including streaming services. Watch out – many of the general hotel/reservation websites show this location is having a “rooftop pool,” but it does not have any pool."

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, apart-hotels, 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 favorite 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 depends 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 €180 per night. Entering your travel dates in the search wizard you might find 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?

4BR Modern Urban Escape, Walk to Zoo, Lakefront & Red Line: This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, a BBQ and air conditioning to put you at ease 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.

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