A city skyline with skyscrapers, a river, and a bridge.

Cottages in Cook County

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Dates

November 2026

6

December 2026

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Top cities in Cook County

A large park with a lake, surrounded by residential areas and a distant city skyline.

Find holiday rentals that suit your style

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Check prices for these dates

Next weekend

13 Nov - 15 Nov

In two weeks

20 Nov - 22 Nov

In one month

In two months

Map of Cook County

Our top choices for Cook County cottages

A two-story house with a red door, brick exterior, and a front yard with a lawn and flower beds.

1. Pet-friendly Abode, 2 Mi to Dtwn Evanston!

South Evanston

A two-story house with a snow-covered front yard and steps leading to the entrance.

2. Private Hot Tub & Patio! Chicagoland Extended Stay

Lansing

A two-story house with a front porch, a staircase leading to the second floor, and a well-maintained garden.

3. Classic Forest Park Foursquare < 1 Mi to Blue Line

Forest Park

Rp8.585.876 total

includes taxes & fees

9 Nov - 10 Nov

A two-story house with a porch, white picket fence, and a tree in the foreground.

4. Oak Park Home w/ Grill - 5 Mi to Garfield Park!

Oak Park

United States

Magdalena

A two-story house with a brick exterior, a stone facade, and a front porch.

5. 2 Mi to Northwestern: Updated Home w/ Game Room!

Church & Dodge

United States

Abbie

A two-story house with a front porch, a visible mailbox, and a small garden with various plants and flowers.

6. 8 Mi to Chicago! Near Oak Park Attractions

Oak Park

A two-story house with a garage, a lawn, and trimmed bushes.

7. Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

Matteson

Front of property

8. Shop, Dine & Unwind: Oak Park Home w/ Private Yard

Oak Park

A house with a garage, surrounded by trees and a driveway.

9. Country Club Hills Home: Walk to Rec Center!

Country Club Hills

A single-story house with a front porch, a brick foundation, and a small garden with various flowers.

10. Private Backyard! Chicagoland Ranch Retreat

Harvey

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Top reviews in Cook County

A modern hotel lobby with a long blue sofa, numbered cushions, and hanging planters.

Hilton Vacation Club Hotel Blake Chicago

Downtown Chicago

10/10 Excellent

United Kingdom

Kanokkan

A high-rise building with a modern glass facade, surrounded by other tall buildings.

Residence Inn Chicago Downtown Magnificent Mile

Downtown Chicago

10/10 Excellent

United Kingdom

Christopher

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

Hotel Riu Plaza Chicago

Downtown Chicago

10/10 Excellent

United Kingdom

Satish

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

The Royal Sonesta Chicago Downtown

Downtown Chicago

10/10 Excellent

United Kingdom

PATRICK

A modern high-rise building with a glass facade, surrounded by other tall buildings.

citizenM Chicago Downtown

Downtown Chicago

10/10 Excellent

United Kingdom

Rebecca

A high-rise hotel with a modern glass facade, multiple floors, and a prominent corner entrance.

Residence Inn by Marriott Chicago Downtown / River North

Downtown Chicago

10/10 Excellent

United Kingdom

Katarzyna

A modern building with a glass facade, multiple floors, and a prominent 'Alo' sign.

Aloft by Marriott Chicago Downtown River North

Downtown Chicago

10/10 Excellent

United Kingdom

Zach

A multi-story building with a grid of windows, surrounded by other high-rise buildings.

Staypineapple, An Iconic Hotel, The Loop

Downtown Chicago

10/10 Excellent

United Kingdom

Mathew

A hotel with a prominent entrance, multiple flags, and a large building facade.

InterContinental Chicago Magnificent Mile by IHG

Downtown Chicago

10/10 Excellent

United Kingdom

David

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