Winnetka Holiday Rentals, Chicago: Private House Rentals

Our top choices for Winnetka hotels

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The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Anna

4.806.702 ₫ total

includes taxes & fees

27 Jul - 28 Jul

Outdoor pool, pool cabanas (surcharge), pool umbrellas

DoubleTree by Hilton Chicago - Magnificent Mile

Downtown Chicago

Drew

6.018.255 ₫ total

includes taxes & fees

10 Aug - 11 Aug

Sofitel Chicago Magnificent Mile

Downtown Chicago

Siobhan

9.747.460 ₫ total

includes taxes & fees

9 Aug - 10 Aug

Sheraton Grand Chicago Riverwalk

Downtown Chicago

Leigh Lynne

9.338.211 ₫ total

includes taxes & fees

19 Jul - 20 Jul

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Julie

8.823.181 ₫ total

includes taxes & fees

19 Jul - 20 Jul

Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Danny

4.862.701 ₫ total

includes taxes & fees

10 Aug - 11 Aug

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Downtown Chicago

Cestra

7.392.637 ₫ total

includes taxes & fees

11 Aug - 12 Aug

Silversmith Hotel Chicago Downtown

Downtown Chicago

Taylor

5.795.131 ₫ total

includes taxes & fees

9 Aug - 10 Aug

Hotel Riu Plaza Chicago

Downtown Chicago

Gary

6.838.922 ₫ total

includes taxes & fees

9 Aug - 10 Aug

Hilton Garden Inn Chicago Downtown South Loop

Downtown Chicago

Nathaniel

5.107.552 ₫ total

includes taxes & fees

10 Aug - 11 Aug

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

Downtown Chicago

Kathleen

7.776.572 ₫ total

includes taxes & fees

16 Jul - 17 Jul

FOUND Hotels, Chicago, Series by Marriott

Downtown Chicago

Lia

4.563.901 ₫ total

includes taxes & fees

19 Jul - 20 Jul

Hyatt Place Chicago/Downtown - The Loop

Downtown Chicago

Kimberly

5.684.080 ₫ total

includes taxes & fees

9 Aug - 10 Aug

Homewood Suites by Hilton Chicago-Downtown

Downtown Chicago

Cynthia

6.632.884 ₫ total

includes taxes & fees

19 Jul - 20 Jul

Warwick Allerton - Chicago

Downtown Chicago

Peter Anthony

5.133.385 ₫ total

includes taxes & fees

12 Aug - 13 Aug

Freehand Chicago

Downtown Chicago

Charles

4.753.014 ₫ total

includes taxes & fees

27 Jul - 28 Jul

55-inch LCD TV with cable channels, TV, pay films

L7 Chicago by LOTTE

Downtown Chicago

Raul

9.050.806 ₫ total

includes taxes & fees

3 Aug - 4 Aug

Hyatt Centric The Loop Chicago

Downtown Chicago

Vikram Surana

6.852.424 ₫ total

includes taxes & fees

19 Jul - 20 Jul

Superior Apartment, 2 Bedrooms, Kitchen | Living area | LED TV, Netflix, Hulu, streaming services

LIVN - West Loop Chicago

Downtown Chicago

Pedro

7.493.435 ₫ total

includes taxes & fees

16 Jul - 17 Jul

Swissotel - Chicago

Downtown Chicago

Scott

7.924.044 ₫ total

includes taxes & fees

26 Jul - 27 Jul

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Stay near popular Winnetka attractions

Chocolate Box

Enjoy a stop at Chocolate Box, an entertaining place to visit in Winnetka. Attend a sporting event or simply enjoy the top-notch restaurants while you're in the area.

See properties

Learn more about Winnetka

Elegant North Shore homes line the streets near Lake Michigan beaches where locals picnic during summer festivals. Explore the historic Crow Island School's architecture or catch a show at the Winnetka Community House theatre.

See all hotels in Winnetka

A suburban street with a stone house, a tree, and a clear sky.

Top Winnetka Hotel Reviews

Hilton Chicago O'Hare Airport

8/10 Good

"Property is showing its age and not modern."

Omni Chicago Hotel

8/10 Good

"Staff was amazing, we had a single king bed corner suite with a separate room that has a pull out bed from the couch. It was a perfect setup for us because the kids had their own little room with their own tv and everything. The pullout couch bed was very uncomfortable, but we kinda figured it wouldn't be the best in the first place so that was alright. The king bed was pretty good, no complaints there... What we disliked was that the room was not properly cleaned before us. They didn't vacuum, there were beer caps and change on the floor. The toilet was for sure not cleaned after the last guests in the room because it was pretty bad. There were only two bath towels which wasn't a big deal cause they brought us more and they also brought us a microwave after asking, that was pretty nice. The really stupid thing with the king bed room was that the TV is literally all the way over to the left mounted on the wall where you couldn't see it very well while laying in bed... It is really really stupid if you see what im talking about here. Imagine laying in bed at a $300 a night hotel and you and your wife are trying to watch a TV thats WAY over on the left side of the room... Its actually comical how the set up is... Valet parking is insane at $90 a night so I would recommend finding parking elsewhere around the hotel if you can. Overall it was a OK stay, nothing incredible and definitely not worth the $300 plus $90 parking..."

Hyatt Regency Chicago

8/10 Good

"Plan on a $100 a night deposit. $100 parking. All things that aren't clear when you book this hotel. I was gouged for a $700 unexpected deposit for 6 nights. I had booked a room that was supposed to include the parking but nope had to pay the $100 a day for that too. Be prepared to automatically lose $1000 before you even walk into your room."

More cheap stays in Winnetka

Quality Inn O'Hare Airport

3801 North Mannheim Road Schiller Park IL

2.285.140 ₫

2.627.454 ₫ total

4 Aug - 5 Aug

includes taxes & fees

7.6/10 Good! (2,220 reviews)

Hotels in Winnetka with star rating

Frequently asked questions

What's the seasonal weather in Winnetka?

The hottest months are usually July and August, with an average temperature of 21°C, while the coldest months are January and February, with an average of -1°C. Average annual precipitation for Winnetka is 1216 mm.

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Our top choices for Winnetka hotels

The Chicago Hotel Collection Ambassador Gold Coast

DoubleTree by Hilton Chicago - Magnificent Mile

Sofitel Chicago Magnificent Mile

Sheraton Grand Chicago Riverwalk

Sable at Navy Pier Chicago, Curio Collection by Hilton

Travelodge by Wyndham Downtown Chicago

Embassy Suites by Hilton Chicago Downtown Magnificent Mile

Silversmith Hotel Chicago Downtown

Hotel Riu Plaza Chicago

Hilton Garden Inn Chicago Downtown South Loop

THE MIDLAND HOTEL, Chicago, a Tribute Portfolio Hotel

FOUND Hotels, Chicago, Series by Marriott

Hyatt Place Chicago/Downtown - The Loop

Homewood Suites by Hilton Chicago-Downtown

Warwick Allerton - Chicago

Freehand Chicago

L7 Chicago by LOTTE

Hyatt Centric The Loop Chicago

LIVN - West Loop Chicago

Swissotel - Chicago

Stay near popular Winnetka attractions

Chocolate Box

Learn more about Winnetka

Top Winnetka Hotel Reviews

Hilton Chicago O'Hare Airport

More cheap stays in Winnetka

Quality Inn O'Hare Airport

Hotels in Winnetka with star rating

Frequently asked questions

Explore a world of travel with Expedia

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