Winnetka Holiday Rentals, Chicago: Private House Rentals

Our top choices for Winnetka hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Downtown Chicago

Gina

8.733.017 ₫ total

includes taxes & fees

14 Jun - 15 Jun

Freehand Chicago

Downtown Chicago

Michael

6.138.921 ₫ total

includes taxes & fees

10 Jun - 11 Jun

The Chicago Hotel Collection Ambassador Gold Coast

Downtown Chicago

Robin

4.894.019 ₫ total

includes taxes & fees

24 Jun - 25 Jun

Hilton Chicago/Magnificent Mile Suites

Downtown Chicago

Nereida

5.734.272 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Congress Plaza Hotel

Downtown Chicago

Jennifer

6.585.303 ₫ total

includes taxes & fees

2 Jun - 3 Jun

Silversmith Hotel Chicago Downtown

Downtown Chicago

Brittany

5.809.914 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Travelodge by Wyndham Downtown Chicago

Downtown Chicago

Amber

4.198.788 ₫ total

includes taxes & fees

28 Jun - 29 Jun

The Chicago Hotel Collection - Magnificent Mile

Downtown Chicago

Ontario

4.759.190 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Hotel Riu Plaza Chicago

Downtown Chicago

sierra

8.234.477 ₫ total

includes taxes & fees

16 Jun - 17 Jun

Hampton Inn Majestic Chicago Theatre District

Downtown Chicago

Eric

5.562.374 ₫ total

includes taxes & fees

28 Jun - 29 Jun

2 restaurants; breakfast, lunch, and dinner served

LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Matson

7.320.067 ₫ total

includes taxes & fees

21 Jun - 22 Jun

Eurostars Magnificent Mile

Downtown Chicago

Belinda

6.763.147 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Omni Chicago Hotel

Downtown Chicago

Alejandro

6.356.983 ₫ total

includes taxes & fees

7 Jun - 8 Jun

Warwick Allerton - Chicago

Downtown Chicago

Natalia

5.469.592 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Hotel Chicago Downtown, Autograph Collection by Marriott

Downtown Chicago

enma

5.761.396 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Hilton Chicago

Downtown Chicago

Robert

9.352.177 ₫ total

includes taxes & fees

7 Jun - 8 Jun

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Downtown Chicago

Rachael Lindsay

5.986.637 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Millennium Hotel Knickerbocker Chicago

Downtown Chicago

Eileen

4.884.550 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

Brenda

7.797.892 ₫ total

includes taxes & fees

28 Jun - 29 Jun

Residence Inn Chicago Downtown Magnificent Mile

Downtown Chicago

Niranjan

6.637.904 ₫ total

includes taxes & fees

28 Jun - 29 Jun

View all properties

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

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

Stinson Memorial Library Anna Illinois Listed on the National Register Funded by Anna businessman Robert Burns Stinson, designed by Walter Burley Griffin who studied under Frank Lloyd Wright.

Top Winnetka Hotel Reviews

River Hotel

6/10 Okay

"The WiFi was not good. Very slow and not helpful. Everything else about the stay was great"

Hotel Riu Plaza Chicago

10/10 Excellent

"The location could not be better. It was half a block to Michigan Avenue, and there was a bus stop at the corner. Several restaurants and too many stores to count were within walking distance. The room was very nice, comfortable, and well lit, despite not being very large. I enjoyed having a handheld option for the shower, while my wife liked the rainfall shower head. There wasn't a lot of room on the vanity, largely because there were 2 sinks. The square toilet was a big negative, because the seat opening was too wide. It was also a bit inconvenient to have to keep the room key inserted in a slot by the door in order to have electricity; every time we took the key out of the slot, the power shut off, so I had to reprogram my CPAP every night. The breakfast buffet was incredible. The variety of hot foods, fruit, and pastries was impressive. Unfortunately, it was very difficult to get an elevator during breakfast hours. The bellhops were very prompt and friendly. Our air was not working the night we arrived. We put in a maintenance request, and within 15 minutes someone came to the room and fixed it, even though it was nearly midnight. It would be nice if they had a small shop to get snacks and soft drinks to take to the room. The hotel does not have parking, and they don't have an arrangement with any of the nearby garages. I was able to find a garage a couple of blocks away, but it would have been nice to be able to make parking arrangements in advance."

DoubleTree by Hilton Chicago - Magnificent Mile

10/10 Excellent

"The pool/lounge area was amazing! Provided a great view and a wonderful place to relax right in the middle of the city! Every staff member we encountered was exceptionally friendly and helpful. Located just off Michigan Ave but still in a great location with easy access to so many Chicago sites. Would definitely stay here again."

More cheap stays in Winnetka

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

22 West Algonquin Road Arlington Heights IL

1.635.788 ₫

1.831.756 ₫ total

5 Jun - 6 Jun

includes taxes & fees

5.4/10 (1,001 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.

Explore a world of travel with Expedia

Book Hotels in Winnetka on Expedia.com

Find hotels in Winnetka, IL from 1.831.756 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winnetka

Check prices for these dates

Filter by

Our top choices for Winnetka hotels

Sable at Navy Pier Chicago, Curio Collection by Hilton

Freehand Chicago

The Chicago Hotel Collection Ambassador Gold Coast

Hilton Chicago/Magnificent Mile Suites

Congress Plaza Hotel

Silversmith Hotel Chicago Downtown

Travelodge by Wyndham Downtown Chicago

The Chicago Hotel Collection - Magnificent Mile

Hotel Riu Plaza Chicago

Hampton Inn Majestic Chicago Theatre District

LondonHouse Chicago, Curio Collection by Hilton

Eurostars Magnificent Mile

Omni Chicago Hotel

Warwick Allerton - Chicago

Hotel Chicago Downtown, Autograph Collection by Marriott

Hilton Chicago

Bluegreen Vacations Hotel Blake, an Ascend Collection Hotel

Millennium Hotel Knickerbocker Chicago

Staypineapple, An Iconic Hotel, The Loop

Residence Inn Chicago Downtown Magnificent Mile

Stay near popular Winnetka attractions

Chocolate Box

Learn more about Winnetka

Top Winnetka Hotel Reviews

River Hotel

More cheap stays in Winnetka

Red Roof Inn Chicago-O'Hare Airport/ Arlington Hts

Hotels in Winnetka with star rating

Frequently asked questions

Explore a world of travel with Expedia

Go further with the Expedia app