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

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

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

A kitchen counter with a microwave, two large containers, and baskets of bread and pastries.

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

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.

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

A reception desk with a "Welcome to the Prairie State" sign, a Hilton Honors sign, and a wooden wall with a herringbone pattern.

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

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

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

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

5.915.633 ₫

7.802.529 ₫ 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 restaurant with high ceilings, wooden flooring, and a central chandelier. Tables are set with wine glasses and red cushions.

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

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

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 spacious lobby with a marble floor, a reception desk, and a glass partition.

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.

9. Hotel Riu Plaza Chicago

Downtown Chicago

Kevin

4.543.467 ₫

6.139.079 ₫ total

includes taxes & fees

11 Nov - 12 Nov

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

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

A modern hotel room with a large window offering a cityscape view, a green sofa, two armchairs, and a coffee table with flowers.

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.

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

A modern dining area with a white marble table, blue upholstered chairs, and a black pendant light.

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

11. Chez Hotel Arlington Heights

Arlington Heights

darcie

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 breakfast table with croissants, a bowl of berries, a glass of orange juice, and a smoothie, set against a cityscape view through a window.

12. The Royal Sonesta Chicago Downtown

Downtown Chicago

Jose

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

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

A multi-level hotel lobby with a glass elevator, a seating area, and a dining space.

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 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.

A modern interior with wooden flooring, black furniture, and large windows offering city views.

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

A multi-story hotel with a modern glass facade, located in an urban setting with a parking lot and street views.

A vending machine with various beverages and snacks.

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

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

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

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

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

17. Eurostars Magnificent Mile

Downtown Chicago

Will

3.725.568 ₫

4.429.328 ₫ total

includes taxes & fees

9 Nov - 10 Nov

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

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.

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

18. Fairmont Chicago at Millennium Park

Downtown Chicago

Ruby

6.575.110 ₫

8.740.002 ₫ total

includes taxes & fees

4 Nov - 5 Nov

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

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.

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

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 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.

A modern hotel room with a cityscape view, a bed, a desk, a coffee machine, and a purple sofa.

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

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!"

River Hotel

10/10 Excellent

"The staff was so friendly. Especially Jock at the front desk was excellent. We loved the location, the view of the river, the 2nd floor coffee lounge and the water stations on each floor. I wish there was a restaurant in house, but we managed. I would definitely stay here again."

Sports Illustrated Resorts Chicago

10/10 Excellent

"Since Our flight kept being delayed; we arrived very early next day. We notified the front desk when this was happening. Upon our arrival, we were greeted with a friendly front desk person. Our room was ready. The room was spacious. It was beautiful. Staff in the front desk were very friendly and helpful."

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

25 Oct - 26 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

22 Oct - 23 Oct

includes taxes & fees

6.8/10 (2,345 reviews)

Comfort Inn Chicago Schaumburg - O'Hare Airport

1300 E Higgins Rd Schaumburg IL

2.226.544 ₫

2.560.080 ₫ total

22 Oct - 23 Oct

includes taxes & fees

7.2/10 Good! (1,005 reviews)

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)

Travelodge by Wyndham Downtown Chicago

65 E Harrison St Chicago IL

3.166.733 ₫

3.764.928 ₫ total

10 Nov - 11 Nov

includes taxes & fees

Hampton Inn Chicago Downtown/Magnificent Mile

160 E Huron Street Chicago IL

4.357.081 ₫

5.180.133 ₫ total

2 Nov - 3 Nov

includes taxes & fees

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

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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

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

River Hotel

Sports Illustrated Resorts Chicago

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-O'Hare International Airport

Travelodge by Wyndham Downtown Chicago

Hampton Inn Chicago Downtown/Magnificent Mile

Hotels in Winnetka with star rating

Frequently asked questions

Explore a world of travel with Expedia

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