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Vacation rentals in Cook County

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Top-rated holiday rentals in Cook County

Guests agree: these stays are highly rated for location, cleanliness, and more.

The Wheaton Bungalow- A Block From Wheaton College
Entire bungalow · 4 guests · 3 beds · 1 bath
The Wheaton Bungalow- A Block From Wheaton CollegeCome stay in this classic Chicago style bungalow located just 1.5 from Downtown Wheaton. This cozy 2 bedroom/1 bath is the perfect little getaway if you’re visiting Wheaton. The house features an updated kitchen, a fenced in yard, a king bed with a hybrid purple mattress and down comforters where you’ll get the best night sleep you’ve ever had. Located just a few blocks away from Wheaton College, this is the perfect place to stay if visiting the college.
Private Studio in Bridgeport, Chicago
SUPERHOST
Entire guesthouse · 3 guests · 1 bed · 1 bath
Private Studio in Bridgeport, ChicagoA bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.
Gorgeous, cozy 1-bedroom Suite in Andersonville
SUPERHOST
Entire guest suite · 2 guests · 1 bed · 1 bath
Gorgeous, cozy 1-bedroom Suite in AndersonvilleOur place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, the location and of course, complete privacy. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

Holiday rentals for every style

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Popular amenities for Cook County holiday rentals

  • Kitchen
  • Wi-Fi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Cook County

  1. Private room
  2. Chicago
Charming Basement with Private Bath- Sleeps 2
$27 AUD per night
SUPERHOST
  1. Private room
  2. Willow Springs
Catmandu 2
$56 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Palos Hills
Aunt Linda's Apartment with a View in Palos
$129 AUD per night
SUPERHOST
  1. Entire residential home
  2. Worth
The Comfy King Ranch /King Bed/Fast WiFi/Free Pkg
$279 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
$126 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Evanston
Charming studio apartment
$139 AUD per night
  1. Entire condominium (condo)
  2. Chicago
Home Office/Quiet Location/Walkable/Fast WiFi
$127 AUD per night
SUPERHOST
  1. Entire guest suite
  2. Naperville
Lake facing private studio with private entrance.
$64 AUD per night
  1. Entire rental unit
  2. Oak Park
1 bed 1 bath apartment 42-1
$77 AUD per night
SUPERHOST
  1. Entire guesthouse
  2. Oak Park
Coachhouse in central OP 4 blk to L
$130 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Forest Park
Walk to Oak Park from this Newly Remodeled Gem
$134 AUD per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Cozy loft in Chicago's Uptown near CTA/Red Line
$150 AUD per night