Winnetka Holiday Rentals from NZ$228: Search Short-Term Rentals

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

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony : This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, an arcade/games room 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.

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Our top choices for Winnetka holiday rentals

Apartment in Downtown Chicago

Tyler B.

includes taxes & fees

25 Mar - 26 Mar

Apartment in Downtown Chicago

Alana C.

includes taxes & fees

23 Mar - 24 Mar

Aparthotel in Downtown Chicago

Marshal

includes taxes & fees

1 Apr - 2 Apr

1 bedroom, iron/ironing board, travel cot, WiFi

Apartment in Downtown Chicago

Greg C.

includes taxes & fees

22 Mar - 23 Mar

Aparthotel in Downtown Chicago

Tomeka

Desk, iron/ironing board, travel cot, WiFi

Apartment in Downtown Chicago

Brianna K.

includes taxes & fees

26 Mar - 27 Mar

Apartment in Downtown Chicago

Jennifer M.

includes taxes & fees

30 Mar - 31 Mar

Apartment in Lincoln Square

SHERI C.

includes taxes & fees

22 Mar - 23 Mar

Apartment in Downtown Chicago

Jiri N.

includes taxes & fees

22 Mar - 23 Mar

Apartment in North Center

Carin O.

includes taxes & fees

22 Mar - 23 Mar

Apartment in Northlake

Yafeat D.

includes taxes & fees

22 Mar - 23 Mar

Full-sized fridge, microwave, oven, stovetop

Aparthotel in Downtown Chicago

Marcus

includes taxes & fees

22 Mar - 23 Mar

Holiday Home in Oak Park

Fred D.

includes taxes & fees

20 Apr - 21 Apr

Holiday Home in Mundelein

Erika H.

includes taxes & fees

22 Mar - 23 Mar

Apartment in Uptown

Darryl C.

includes taxes & fees

22 Mar - 23 Mar

Condo in Oak Park

Michael W.

includes taxes & fees

31 Mar - 1 Apr

Apartment in Lincoln Square

Kaitlin T.

includes taxes & fees

24 Mar - 25 Mar

Apartment in Near West Side

Kourtney K.

includes taxes & fees

23 Mar - 24 Mar

Apartment in Lincoln Square

Ticia B.

includes taxes & fees

25 Mar - 26 Mar

Apartment in Lakeview

Matthew B.

includes taxes & fees

23 Mar - 24 Mar

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Top Winnetka Hotel Reviews

Congress Plaza Hotel

10/10 Excellent

"Clean room"

Embassy Suites by Hilton Chicago Downtown River North

6/10 Okay

"In effective security as one of the nights, there were young kids running up and down the hall at midnight and another night there was such a loud fight that we were afraid of violence. One morning, there was no hot water Furniture was dusty."

Swissotel - Chicago

10/10 Excellent

"We love this hotel and always stay here when needing to stay in the North Loop area. The property is dog friendly and staff is very attentive. Our daughter wished there was a pool and I a hot tub, but for the price, the room, the staff, the view and walkability it is great! There is a dog park about a block away behind the CVS down the street. There is an elevator there or a LOT of stairs if you're bringing your doggo. Otherwise, there are close spots right outside for middle of the night potty runs. Overall, great property!"

Hotel Riu Plaza Chicago

10/10 Excellent

"We had a very pleasant stay overall. Wonderful location, nice room, very clean. Staff were consistently warm, attentive, and eager to help with anything we needed. Breakfast was another highlight. There was a great variety of options, with something for everyone, and everything we tried was fresh and well-prepared. The only challenge during our stay was the elevators. Maybe some of them were not in service? They were often very slow or crowded, which led us to take the stairs at one point from the 8th floor. Unfortunately, when we reached the second floor for breakfast, we found that the stairwell door was locked, which was a bit inconvenient. Avoid rush hour! That said, the excellent service and great breakfast made up for the small inconvenience, and I would still consider staying at Riu many times again."

Hilton Chicago/Magnificent Mile Suites

8/10 Good

"The bathrooms need updating. The shower floor is chipping. There are cracks between the wall and floor of shower. There is water damage on the base of bathroom door. Which is "bubbling" up. One can see that instead of replacing door. It has been painted over repeatedly. The wall socket near the nightstand is a loose socket. It won't grip the plug. There was a stinch smell in the suite. As if the carpet needed to be cleaned. We has to buy an air freshener. The staff was wonderful."

The Chicago Hotel Collection Ambassador Gold Coast

6/10 Okay

"The room was cleen enough, it smelled musty, but looked clean, rather out dated, IKEA furnished. Staff was friendly. I was told on check-in that i owed more money for the amenities, which was quite expensive for breakfast and a cocktail ($125/person) the hotel itself is pretty worn around the edges. I was awoken at 715 am to construction on the facade outside my window and was offered a new room for the remaining 4 hours rather than a reduction in rates. Kinda disappointed "

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 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 NZ$228 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?

HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony: This holiday home rental outside of Winnetka is located in the city centre, and has a balcony, an arcade/games room 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.

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.

Winnetka Holiday Rentals

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Check prices for these dates

Our top choices for Winnetka holiday rentals

Apartment in Downtown Chicago

Apartment in Downtown Chicago

Aparthotel in Downtown Chicago

Apartment in Downtown Chicago

Aparthotel in Downtown Chicago

Apartment in Downtown Chicago

Apartment in Downtown Chicago

Apartment in Lincoln Square

Apartment in Downtown Chicago

Apartment in North Center

Apartment in Northlake

Aparthotel in Downtown Chicago

Holiday Home in Oak Park

Holiday Home in Mundelein

Apartment in Uptown

Condo in Oak Park

Apartment in Lincoln Square

Apartment in Near West Side

Apartment in Lincoln Square

Apartment in Lakeview

Find holiday rentals that suit your style

Top Winnetka Hotel Reviews

Congress Plaza Hotel

Find out more about Winnetka

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