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Holiday 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.

Mid-Century Modern Charm. Close to Chicago.
Entire rental unit · 4 guests · 3 beds · 1 bathroom

Mid-Century Modern Charm. Close to Chicago.Step back in time a bit with our charming 2nd floor walk-up in a quiet suburb. Newly remodeled but with a vintage, welcoming vibe. A short walk to the train or a 20-minute drive to downtown Chicago. We live downstairs and are happy to say hi, or happy to leave you in peace, whichever you prefer. Free Parking. Great wifi. 3-season back porch. Feel free to relax in our welcoming back yard. Record Player (Real Vinyl!)

Aunt Linda's Apartment with a View in Palos
Entire rental unit · 6 guests · 4 beds · 1 bathroom

Aunt Linda's Apartment with a View in PalosSunny, quiet first floor 2 bedroom apartment in owner occupied 4-Flat apartment building. It is located in the Southwest corner of Chicago’s Cook County. [Note: long term stays are available.] The building's eastern view overlooks the southern suburbs of Chicago Ridge, Oak Lawn and Bridgeview.

Gorgeous, cozy 1-bedroom Suite in Andersonville
Entire guest suite · 2 guests · 1 bed · 1 bathroom

Gorgeous, cozy 1-bedroom Suite in AndersonvilleOur place is close to many shops, great ethnic restaurants, food markets, coffee shops, lounges and even 3 breweries. You’ll love my place because of the ambiance, the neighborhood, the outdoor space 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
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in Cook County

  1. Entire residential home
  2. Darien
Cozy Studio on the Lower Level of the House.
₹3,890 per night
  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from 1920's Room 1A
₹7,338 per night
  1. Entire guest suite
  2. Naperville
Lake facing private studio with private entrance.
₹3,533 per night
  1. Entire guest house
  2. Chicago
Private Coach house near Lincoln Square!
₹8,232 per night
  1. Entire rental unit
  2. Chicago
Great location. Free parking.
₹6,350 per night
  1. Private room
  2. Willow Springs
Catmandu 2
₹3,049 per night
  1. Entire guest house
  2. Countryside
Cozy Cottage Minutes from Downtown Chicago
₹7,223 per night
  1. Entire rental unit
  2. Chicago
Enjoy Chicago’s Nightlife from Studio Apartment
₹6,729 per night
  1. Entire guest house
  2. Wheaton
Cozy private coach house in Wheaton
₹8,232 per night
  1. Private room
  2. Woodridge
Private floor with living room and office space
₹2,208 per night
  1. Entire guest suite
  2. Wheaton
Fully Private, Modern Studio Apartment!
₹6,392 per night
  1. Entire cottage
  2. Merrillville
The Hideaway
₹5,951 per night

Top-rated things to do in Cook County

Unique activities hosted by local experts vetted for quality

  • Gangsters and Ghosts Tours
    One of the best ways to really acquaint yourself with the infamous city of Chicago is to do it from the streets, through a guided Chicago Gangster Tour or Ghost Tour, detailing the crimes, deals, and charisma that made the city what it is today. We offer a 2 for 1 deal, hosting historically-based guided tours of Chicago’s gangers AND ghost stories, right from the Chicago Loop Vice District. Other things to note Bring your camera!
    From Price:₹1,988/person
    IF YOU DON´T SEE A TIME FRAME THAT WORKS FOR YOU PLEASE CONTACT ME AND WE CAN ARRANGE THAT We’ll start with a talk in Chicago Cultural Center by the bull and get to know each other. If it’s a small group during the experience, we will walk together around various locations but everybody has their own personal time with me while I photoshoot. Together we’ll discover the places and pictures that YOU NEED TO HAVE from Chicago , from the magical MILLENNIUM PARK, THE BEAN , CHICAGO THEATER AND RIVER WALK while I capture moments of you and/or any friends or your partner to take home. Feel free to tell me your ideas or preferences Other things to note THIS IS A SMALL GROUP EXPERIENCE AND EVERYBODY HAS THEIR OWN TIME (YOU CAN ALSO HAVE PRIVATE PHOTO SHOOTINGS IN CASE THAT YOU NEEED SOMETHING MORE PRIVATE) Please feel free to visit more of my work at also on IG at carrascoocampo
    From Price:₹7,213/person
  • Explore Dazzling Architecture Interiors
    Take the architecture tour voted #1 by TripAdvisor users! We will be taking a leisurely 2-hour walk exploring some of the most beautiful and often overlooked buildings in downtown Chicago, both outside and inside, and learning about the most important and interesting parts of Chicago's architectural history. Visitors often don't know where to go, or even where they're allowed. This experience takes them inside places they'd never even consider, to show off more than 100 years of architecture as it developed here in the Windy City -- including stunning stained glass, atrium-like spaces, 19th century skyscrapers, and more! Great tour for photographers and travel buffs! Some things to note: Bring a camera -- this is an AWESOME way to practice your architecture photography! Also, dress for the weather, and if it's raining, bring an umbrella. Also, please note that if you provide a non-US phone number as your day-of contact number, we **CANNOT** call you if you're lost or late!
    From Price:₹2,208/person
  • Read and Learn Tarot At the Lake
    Everyone has intuition so anyone can listen and read it accurately. Your session will consist of: 1) An individual intuitive reading 2) Then teach you how to do it with each performing a personal reading 3) Send you home with instructions and spiritual tool recommendations. I can do at my place, where you are staying in the area (if 30 minutes or less), or via zoom. The choice is up to each participant Here are some of my reviews. Suzanne is a gifted medium who instantly tapped into a meaningful connection. Steele eased my first-time jitters with her kindness, taking her time, finding deeper guidance than I ever expected from a single reading. I found her reading possessed spot-on relevance and I felt her presence was warm, inviting, full of light and encouragement. I highly recommend this tarot reading experience to anyone seeking higher guidance in any aspect of life, whether you've had prior readings with other mediums or if this is your first experience. I will definitely continue working with Steele because she exudes generosity of spirit and compassion beyond measure. Her reading was a pleasure, something I wish to experience again. Jenn Diamond
    From Price:₹1,840/person
  • All-Weather Architecture & History Trek
    I pack lots of sights, sounds and experiences on this tour so put on your walking shoes! We first meet in a sheltered spot to discuss the tour and begin our way trekking through Chicago. We'll use the expansive city sidewalks, plazas, parks and Riverwalk as well as part of the underground Pedway system that is known to only a percentage of Chicagoans (we have 5 miles of Pedway!). Learn about the history of The Windy City (as well as why we're REALLY called The Windy City) while digesting some of our city's most prominent sights. Using some of the Loop's buildings and sculptures, we'll get rare, unique views and traverse the city like a local. If you're curious about Prohibition-era gangster lore or our speakeasy past, we can cover that too. Be prepared for indoor and outdoor walking as our trek will take us outside, especially during warmer weather. Please let me know if you have any allergies or food sensitivities, as we’ll be stopping for an authentic Chicago snack that's been around for more than a century. Whether you're a local or this is your first visit, I promise to pack lots of interesting tidbits into our 2 hours together! COVID-19 UPDATE: We're spending more time outside as there is PLENTY to see & keeping the groups small so we can practice safe social distancing.
    From Price:₹2,135/person