Winnetka Holiday Rentals, Chicago: Private House Rentals

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Our top choices for Winnetka hotels

A spacious lobby with a reception desk, seating area, and a large glass door entrance.

A hotel room with a large bed, a desk, a chair, a television, and a sofa.

A multi-story building with a parking lot in front.

A spacious dining area with multiple tables and chairs, large windows, and a central decorative plant.

1. La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

Deerfield

Shane

2.177.129 ₫

2.416.177 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A modern lounge area with leather sofas, a coffee table, and a patterned rug.

A modern living room with a brown leather sofa, a coffee table, and a side table with a lamp.

A hotel room with two beds, a desk, a chair, a TV, and a large window with a city view.

A modern living room with a sectional sofa, a fireplace, and a bar area.

2. Holiday Inn Chicago O'Hare – Rosemont by IHG

Rosemont

Crystal

3.596.208 ₫

4.144.235 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a microwave, a refrigerator, and a coffee machine.

A hotel reception desk with two computer stations, a modern wall design, and a visible window.

A large conference room with rows of chairs, a stage, and a carpeted floor.

A modern hotel corridor with wooden paneling, a staircase, and a snack bar with various packaged goods.

3. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

Des Plaines

Arlene

3.389.232 ₫

3.998.615 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A three-tiered fruit basket on a wooden table against a wall with framed pictures.

A motel reception desk with a clock, a welcome sign, and a sign listing room types and rates.

A hotel room with two beds, a large window with a city view, a painting on the wall, and a lamp on the nightstand.

A multi-story hotel with a modern design, featuring balconies with railings, large windows with curtains, and a parking area in front.

4. Heart O' Chicago

Edgewater

Oscar

2.864.030 ₫

3.362.325 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A spacious lounge area with leather sofas, a coffee table, and a patterned rug.

A modern kitchen with a dining area, wooden flooring, and a black staircase.

A modern lounge area with a sectional sofa, a fireplace, and a bar with stools.

A spacious room with large windows, a sofa, a dining table, and a small round table with a lamp.

5. Staybridge Suites Chicago O'Hare - Rosemont by IHG

Rosemont

Yoeshua

3.699.696 ₫

4.307.465 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern hotel lobby with round tables, blue upholstered chairs, and large windows offering a view of the outdoors.

A Hampton Inn hotel with a modern facade, large windows, and a welcoming entrance.

An indoor swimming pool with clear windows, green chairs, and a tiled deck.

A hotel room with two beds, a desk, a chair, a TV, and a window with a view.

6. Hampton Inn Chicago-O'Hare International Airport

Schiller Park

Jennifer

3.234.000 ₫

3.718.453 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A rooftop terrace with outdoor seating, a view of the city skyline, and a river.

A modern room with a view of a river and high-rise buildings.

A modern hotel room with a large bed, a desk, a sofa, and a view of the city.

A modern hotel room with a desk, a sofa, a coffee machine, a TV, and a unique wall art piece.

7. LondonHouse Chicago, Curio Collection by Hilton

Downtown Chicago

Keeven

5.937.624 ₫

7.828.674 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A person relaxing on a sofa with a window view of a building, a table with a glass of wine, and a vase with flowers.

A modern hotel lobby with leather sofas, a coffee table, and a floor lamp.

A bar area with a long counter, multiple shelves of bottles, and four bar stools.

A modern restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

8. L7 Chicago by LOTTE

Downtown Chicago

Jeffrey Thomas

4.757.085 ₫

5.655.697 ₫ total

includes taxes & fees

11 Nov - 12 Nov

The Riu Plaza Chicago Hotel facade with a grand entrance, large windows, and a modern architectural design.

A couple dining at a table with a city view, surrounded by chairs and a variety of dishes.

A bar area with a marble countertop, bar stools, and a variety of bottles.

A modern hotel lobby with a central seating area, a reception desk, and a decorative wall with a unique design.

9. Hotel Riu Plaza Chicago

Downtown Chicago

Kevin

4.297.893 ₫

5.847.116 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A dining table set for six with a cityscape view through large windows.

A modern hotel room with a large window offering a city skyline view, a round table with four chairs, and a ceiling with recessed lighting.

The exterior of the Swissotel building with its distinctive glass facade and the hotel's name displayed prominently.

A modern hotel room with a large bed, a desk, a chair, and a view of the cityscape through large windows.

10. Swissotel - Chicago

Downtown Chicago

Hilary

5.471.928 ₫

7.416.787 ₫ total

includes taxes & fees

31 Oct - 1 Nov

A spacious lobby with a marble floor, a central seating area, and a wall of bookshelves.

A rooftop terrace with a central fountain, seating areas, and trees.

A modern bathroom with a glass shower, a round mirror, and a vanity with a marble countertop.

A modern lobby with a marble floor, two elevators, a large abstract painting, and a unique leaf-shaped chandelier.

11. Chez Hotel Arlington Heights

Arlington Heights

Chris

3.047.980 ₫

3.413.293 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A dining area with a table set for four, large windows offering a cityscape view at dusk.

A rooftop terrace with outdoor seating and a fire pit, overlooking a cityscape with tall buildings.

A modern interior with a central fireplace, seating area, and wall-mounted lighting.

A high-rise hotel room with large windows offering a city view, round tables set for dining, and elegant decor with flowers and candles.

12. The Royal Sonesta Chicago Downtown

Downtown Chicago

Jordyn

5.407.248 ₫

7.256.581 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A spacious bar area with high ceilings and large windows, offering views of a cityscape.

A hotel room with a bed, a sofa with cushions, a large window with a view of a cityscape and water.

A bar with a circular liquor display, seating with stools, and a city view through large windows.

A cityscape with modern high-rise buildings, a river, and a boat.

13. Hyatt Regency Chicago

Downtown Chicago

Mercy

6.157.536 ₫

8.243.548 ₫ total

includes taxes & fees

31 Oct - 1 Nov

A modern restaurant interior with a green wall, hanging lights, and a long dining area.

A modern indoor pool area with clear glass walls, lounge chairs, and a view of city buildings.

A rooftop lounge with green cushioned seating, a small round table, and a view of city buildings.

A hotel lobby with a large Christmas tree, a sofa with red and white pillows, a glass coffee table, and a large window with a view of the street.

14. Hotel 505 River North

Downtown Chicago

Giana

4.889.808 ₫

6.641.738 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A restaurant with wooden tables and chairs, large windows, and a green vine-covered ceiling.

A modern living room with a large window, a potted plant, and a variety of seating options including a sofa, armchairs, and ottoman.

A vending machine with various beverages and snacks.

A hotel room with a large bed, two bedside lamps, and a city view through a large window.

15. Hyatt Place Chicago/River North

Downtown Chicago

Iminique

4.398.240 ₫

5.229.067 ₫ total

includes taxes & fees

1 Nov - 2 Nov

The Intercontinental hotel facade with a large American flag and a floral display.

A swimming pool area with a glass-bottomed pool, a high ceiling with hanging lights, and a staircase with people sitting on it.

A bar area with a high bar counter, multiple stools, and a seating area with booths and tables.

A person lying on a bed with a bottle of champagne, surrounded by food and a magazine.

16. InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

Reginald

5.484.864 ₫

7.426.476 ₫ total

includes taxes & fees

31 Oct - 1 Nov

A room with two chairs and a small table, a large window with a city view at night.

A modern living room with a sectional sofa, a round ottoman, a dining area with chairs and a table, and a large mirror on the wall.

A modern hotel lobby with a large window, seating area, and a reception desk.

A modern bar area with a circular seating arrangement, a staircase leading to an upper level, and a view of the city through large windows.

17. Eurostars Magnificent Mile

Downtown Chicago

Will

3.725.568 ₫

4.429.328 ₫ total

includes taxes & fees

10 Nov - 11 Nov

A modern kitchen with a marble island, fruit bowls, and a city view.

A modern bar area with a central bar, seating, and a distinctive ceiling design.

A modern lounge area with a central bar, seating arrangements, and a decorative chandelier.

A Fairmont hotel with a prominent entrance, large windows, and a sculpture on the facade.

18. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

6.575.110 ₫

8.740.002 ₫ total

includes taxes & fees

12 Nov - 13 Nov

A multi-level atrium with a central spiral staircase, multiple seating areas, and a pool.

A spacious lobby with a central staircase, multiple floors, a reception desk, and seating areas.

A swimming pool with a glass wall, a seating area with sofas, and an exit sign.

A multi-story hotel with a prominent 'Embassy Suites' sign, a Starbucks Coffee shop, and a well-lit street at night.

19. Embassy Suites by Hilton Chicago Downtown River North

Downtown Chicago

Eliana

4.376.249 ₫

5.202.922 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern rooftop lounge with white seating, a glass ceiling, and city views.

A rooftop bar with a city skyline view, wooden flooring, and bar stools.

A modern building with a unique architectural design, featuring a mix of glass and concrete materials.

A modern lounge area with seating and tables, large windows offering city views, and a high ceiling with exposed ductwork.

20. The Godfrey Hotel Chicago

Downtown Chicago

3.497.894 ₫

4.740.249 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Winnetka attractions

Elder Lane Beach

This lakefront sanctuary offers a serene escape with pristine sandy shores and Lake Michigan views. Enjoy a peaceful afternoon in the adjacent park with its well-maintained picnic areas and playground.

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Maple Street Beach

Why not spend a lazy afternoon at Maple Street Beach during your trip to Winnetka? Amble around the area's forests or visit its shops.

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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

The Wade

10/10 Excellent

"Will definitely book again"

InterContinental Chicago Magnificent Mile by IHG

10/10 Excellent

"I had wanted to stay here for a long time so I could swim laps in the beautiful pool. It did not disappoint! The hotel location is excellent. Would definitely stay again."

Hilton Chicago O'Hare Airport

8/10 Good

"Very convenient to just walk to your hotel from the airport. Comfortable room. Excellent Fitness facility. I really liked it except for the price! $$$$"

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent

"Nice and quiet"

The Godfrey Hotel Chicago

10/10 Excellent

"Hotel staff were accommodating"

Freehand Chicago

10/10 Excellent

"Perfect location for Chicago marathoners."

The Chicago Hotel Collection - Magnificent Mile

10/10 Excellent

"Just as always- clean and efficient. staff is always helpful and goes above and beyond. Even housekeeping is top notch. do yourself a favor and get the guest benefits pkg. treat yourself!"

More cheap stays in Winnetka

Motel 6 Elk Grove Village, IL - O'Hare

2881 Touhy Ave Elk Grove Village IL

1.547.922 ₫

1.748.842 ₫ total

19 Oct - 20 Oct

includes taxes & fees

Motel 6 Schiller Park, IL - Chicago O'Hare

9408 Lawrence Avenue Schiller Park IL

1.593.456 ₫

1.832.154 ₫ total

20 Oct - 21 Oct

includes taxes & fees

6.8/10 (2,345 reviews)

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL

2.219.041 ₫

2.551.454 ₫ total

26 Oct - 27 Oct

includes taxes & fees

7.2/10 Good! (1,005 reviews)

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

2.824.014 ₫

3.357.469 ₫ total

1 Nov - 2 Nov

includes taxes & fees

8/10 Very good! (1,663 reviews)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

2.980.454 ₫

3.543.463 ₫ total

12 Nov - 13 Nov

includes taxes & fees

Hampton Inn Chicago-O'Hare International Airport

3939 N Mannheim Rd Schiller Park IL

3.234.000 ₫

3.718.453 ₫ total

1 Nov - 2 Nov

includes taxes & fees

9.4/10 Exceptional! (2,400 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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Book Hotels in Winnetka on Expedia.com

Find hotels in Winnetka, IL from 1.748.842 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Winnetka

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Winnetka hotels

1. La Quinta Inn & Suites by Wyndham Bannockburn-Deerfield

2. Holiday Inn Chicago O'Hare – Rosemont by IHG

3. Holiday Inn Express & Suites Chicago O'Hare Airport by IHG

4. Heart O' Chicago

5. Staybridge Suites Chicago O'Hare - Rosemont by IHG

6. Hampton Inn Chicago-O'Hare International Airport

7. LondonHouse Chicago, Curio Collection by Hilton

8. L7 Chicago by LOTTE

9. Hotel Riu Plaza Chicago

10. Swissotel - Chicago

11. Chez Hotel Arlington Heights

12. The Royal Sonesta Chicago Downtown

13. Hyatt Regency Chicago

14. Hotel 505 River North

15. Hyatt Place Chicago/River North

16. InterContinental Chicago Magnificent Mile by IHG

17. Eurostars Magnificent Mile

18. Fairmont Chicago at Millennium Park

19. Embassy Suites by Hilton Chicago Downtown River North

20. The Godfrey Hotel Chicago

Stay near popular Winnetka attractions

Elder Lane Beach

Maple Street Beach

Learn more about Winnetka

Top Winnetka Hotel Reviews

The Wade

InterContinental Chicago Magnificent Mile by IHG

Hilton Chicago O'Hare Airport

The Chicago Hotel Collection Ambassador Gold Coast

The Godfrey Hotel Chicago

Freehand Chicago

The Chicago Hotel Collection - Magnificent Mile

More cheap stays in Winnetka

Motel 6 Elk Grove Village, IL - O'Hare

Motel 6 Schiller Park, IL - Chicago O'Hare

Comfort Inn Chicago Schaumburg - O'Hare Airport

Hampton Inn Chicago Downtown/Magnificent Mile

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago-O'Hare International Airport

Hotels in Winnetka with star rating

Frequently asked questions

Explore a world of travel with Expedia

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