Cook County Vacation Rentals - HolidayHomes base64Hash Cook County Vacation Rentals - HolidayHomes

Cook County Vacation Rentals

Browse 10,570 available vacation homes and compared across 15 trusted partners

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Top-Rated Vacation rentals in Cook County

Book the highest-rated Cook County vacation rentals, rated by real guests for comfort, location, cleanliness, services and value for money

We use AI to generate the short summary in each offer below, check full description before booking.
Aparthotel Evanston

The Gem Museum Suites

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Cabin Barrington

Child-friendly cottage with yard, terrace & grill | Nature view

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House Glenwood

House with barbeque, private pool & terrace

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House Schaumburg

Children-friendly spacious vacation home with private pool, barbeque & garden | Good for workation

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House Des Plaines

Family-friendly lovely vacation home with private pool, garden & grill

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Apartment Evanston

Mid Century Elegance in Evanston: Vintage Apt 2 BR Office / Den Guest Room

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House Crestwood

Vacation home with yard | Pet-friendly

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House Schaumburg

Family-friendly lovely vacation home with garden, pool & BBQ | Good for workation | Pet-friendly

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House Matteson

Children-friendly big house with BBQ & yard | Suitable for remote work | Pets allowed

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House Schaumburg

House with patio & jacuzzi | Suitable for remote work

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House Glenview

Fabulous 4-bedroom house with Inground Pool! On quiet cul-de-sac.

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House Schaumburg

House with BBQ & pool

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House Markham

Vacation home with BBQ, patio & yard | Lake view

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House Evanston

EVANSTON whole building, 2 units combined sleeps 12, 5 bed 5 bath

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House Country Club Hills

Family-friendly house with jacuzzi & terrace | Pets allowed

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Top 15 most Recommended Vacation Rentals in Cook County

Discover your ideal Cook County vacation rental with real-time comparisons of 10,570 properties, featuring recommended options based on the property location, value for money, and verified guest reviews.

We use AI to generate the short summary in each offer below, check full description before booking.
House Olympia Fields
House ∙ 10 guests ∙ 4 bedrooms

Vacation home with barbeque, private pool & patio | Suitable for remote work

Olympia Fields, Rich Township, Cook County
This house rental in Olympia Fields accommodates 10 guests and features a private pool for relaxation and enjoyment.
from $234
per night
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House Des Plaines
House ∙ 9 guests ∙ 3 bedrooms

House with yard, hot tub & terrace | Lake view | Suitable for remote work

Des Plaines, Maine Township, Cook County
This house rental in Des Plaines accommodates 9 guests and features a cozy fireplace for a warm and inviting atmosphere.
from $273
per night
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House Wilmette
House ∙ 6 guests ∙ 3 bedrooms

Child-friendly vacation home | Dogs allowed

Wilmette, New Trier Township, Cook County
Charming house rental in Wilmette accommodates 6 guests and is family-friendly with a spacious yard for outdoor activities.
from $239
per night
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House Worth Township
House ∙ 10 guests ∙ 5 bedrooms

Charming vacation home with jacuzzi | Pets allowed

Worth Township, Cook County, Illinois, United States
Spacious house rental in Worth Township accommodates 10 guests and features a relaxing hot tub for your enjoyment.
from $307
per night
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Condo Homewood
Condo ∙ 4 guests ∙ 2 bedrooms

Beautiful condo | Pet-friendly

Homewood, Thornton Township, Cook County
This Homewood condo accommodates 4 and features a kitchen along with convenient parking.
from $176
per night
(3)
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House Evanston
House ∙ 16 guests ∙ 6 bedrooms

Vacation home with garden, terrace & barbeque | Good for workation

Evanston, Evanston Township, Cook County
Spacious house rental in Evanston for 16 featuring a cozy fireplace and a large yard perfect for family gatherings.
from $513
per night
(13)
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House Evanston
House ∙ 5 guests ∙ 4 bedrooms

Vacation home with jacuzzi, terrace & grill

Evanston, Evanston Township, Cook County
This house rental in Evanston accommodates 5 guests and features a cozy fireplace for a comfortable stay.
from $331
per night
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House Des Plaines
House ∙ 13 guests ∙ 5 bedrooms

Family-oriented house with yard, BBQ & jacuzzi | Suitable for remote work | Pets allowed

Des Plaines, Maine Township, Cook County
from $554
per night
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Villa Hanover Township
Villa ∙ 12 guests ∙ 6 bedrooms

Fully equipped villa with terrace, sauna & grill | Suitable for remote work | Pets allowed

Hanover Township, Cook County, Illinois, United States
This spacious villa in Hanover Township accommodates 12 guests and features a relaxing sauna for ultimate comfort.
from $626
per night
(16)
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