Holiday rentals in Cook County

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Top-rated holiday rentals in Cook County

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Top guest favourite

Private room in Wilmette

4.95 out of 5 average rating, 204 reviews

(BR#2) Welcoming, warm & comfortable, 2 guests

Welcoming, warm & comfortable home, BR#2 for up to 2 guests. (LISTING #2 OF 3; see other listings for additional space.) Located close to Hwy 94. 10 miles from Chicago, close to beach & Wilmette, Evanston, Glenview, Skokie. You're welcome to use all the facilities - kitchen, bathrooms, TV, hi-speed Wifi, laundry & parking. Make your breakfast with supplied basics such as cereal, eggs, juice, tea & coffee. Really friendly small Yorkie-poo dog in the home. Meaningful conversation (if you want it).

Top guest favourite

Private room in Evanston

4.98 out of 5 average rating, 181 reviews

Peaceful Suite with natural light. Shared bath

The Peaceful Suite is located on the 2nd floor at the south end of our home. Our home is nestled in a residential neighborhood, in north Evanston, 1.5 miles west of NU campus, 10 minute walk to NU’s Ryan Field, and a quick jaunt to Central Street’s many fine eateries and boutiques. Sorry but No ADA or wheelchair access. Free permit street parking is available in front of our house. We’ll provide parking permits upon request. Sorry, but the first floor, kitchen and laundry are not included.

Top guest favourite

Home in Lockport

4.96 out of 5 average rating, 138 reviews

Lockports Famous Hideaway ~ 2bdrm Guest House Flat

A history buff’s dream filled with antiques & artifacts relating to Lockport, Chicago, Joliet, I & M Canal & "Route 66"! If you have roots in Illinois or Lockport, the Hideaway is for you! The entire upstairs 1,500 sq ft vintage 2 bedroom house apartment is all your own space. The flat is NOT shared with other guests/host. Family & Business Friendly. Private-entrance/self-check-in. *Can accommodate up to 6 guests. Extra charges apply after 2 guests. Have a 'historic' stay at the "Hideaway"

Superhost

Private room in Oak Park

4.73 out of 5 average rating, 298 reviews

Little Gem Double Rm Home Base for Chicago Trips!

Great home base for Chicago adventures & PREMIUM location in the epicenter of Oak Park - America's home of prairie architecture! Beautiful park/Frank Lloyd Wright homes are directly outside your door and you are only a 25-minute train ride to Millennium Park & all of Chicago! Eclectic garden level (shared) apartment decorated with fun and funky furnishings. Private Bedroom with new double size bed, deluxe bedding, towels. Shared bathroom, living room, and kitchenette. View my other 2 listings!

Guest favourite

Private room in Evanston

4.95 out of 5 average rating, 193 reviews

Welcoming Evanston Home

We have a newly renovated suite awaiting your stay, perfect for one guest. This dedicated entry, private room + bathroom, and tree-lined street are in our quiet neighborhood in beautiful Evanston, just north of Chicago. As international travelers ourselves, we love hosting others from near or far! Enjoy a short walk to cafes, stores, mall shopping, parks, and restaurants. Easy free parking, convenient Uber / Lift rides, and public transportation are also here to make your stay enjoyable.

Guest favourite

Private room in North Riverside

4.93 out of 5 average rating, 216 reviews

The Albany Park Room at the Cape Cod in Riverside

The Cape Cod in Riverside is 10 miles from downtown Chicago, accessible via METRA and CTA Blue Line. It's a block from a trail entrance, a mile from Brookfield Zoo, and close to Riverside's historic downtown and Loyola University Medical Center. O'Hare Airport is 18 miles away, and Midway is 9 miles. The Albany Park Room, one of two Airbnb listings, is on the second floor and accommodates two guests. The property supports sustainability with partial solar energy for heat and hot water.

Guest favourite

Private room in Woodridge

4.86 out of 5 average rating, 501 reviews

Private floor with Bedroom, bathroom, living rm

We are close to all major highways, easy access to go anywhere. Public transportation w/in minutes. Designated parking spot in driveway, also street parking is available. We are next to walking/running trail & parks. Shopping, movies & restaurants are w/in walking distance. Quiet & very safe neighborhood. Shared full kitchen w/ all cook ware available. Private full size fridge/freezer, coffeemaker, toaster oven & microwave. Wifi, streaming, & cable TV. Free on-site laundry & toiletries.

Top guest favourite

Guest suite in Orland Park

4.98 out of 5 average rating, 100 reviews

Private Guest Suite 2 Cozy Rooms

Private guest suite with separate entrance. Sitting room, kitchenette, bedroom w/queen bed, private bath, plus twin sofa bed in sitting room. Great alternative to hotel for business trip or visiting the area. Conveniently located in southwest suburbs of Chicago, 40 minutes from downtown by car (non rush hour) or Metra lines a few miles from the house. Set near a golf course and forest preserve, nearby to multiple restaurant and shopping districts less than 10 minutes away.

Guest favourite

Private room in Des Plaines

4.88 out of 5 average rating, 339 reviews

R1 Delightful room in quiet neighborhood

A cozy room located in peaceful neighborhood, a perfect place to stop after traveling from O'Hare airport! We have a beautiful wild river, lake, and forest right in the backyard and surrounding our area, with wild life creating a cozy atmosphere, amazing to take walks. We are a 10 minute ride from the O'Hare International Airport, a 5 minute ride from a Metra Station, and surrounded by all kinds of parks and interesting restaurants.

Guest favourite

Private room in Richton Park

4.85 out of 5 average rating, 246 reviews

Urbal retreat

On the cusp of urban and rural, urbal. To the north, the sprawling and windy city of Chicago. To the south, farmland and more open spaces. Small bedroom in a nice house on a quiet street. Living space shared with me, my boyfriend, Dillon and my 10 year old son and dog Chase. Walking distance from the train to downtown Chicago. 5 min drive to highway and area with shopping and restaurants.

Guest favourite

Private room in Willow Springs

4.93 out of 5 average rating, 279 reviews

Private bedroom A Quiet Chicago suburb. No parking

Private room on a quiet non-smoking home in a safe suburb. NO PARKING. No OVERNIGHT parking on the streets. 25 minutes to downtown. Bedroom with Queen-size bed for 2 people max. This is 1 of 3 bedrooms available. Natural light bathroom with a sky window is shared with another Airbnb room. Good for tourist, solo, or couples (gay or straight) travelers. NO discrimination allowed.

Guest favourite

Private room in Chicago

4.77 out of 5 average rating, 318 reviews

Chicago River Room near USMLE

R+ My other listings can be found through my profile page. 7 minutes to O'Hare Airport See below for details. Highway entrance 1 block away, so you can easily drive anywhere. Walking distance to pharmacy, shopping mall (including grocery store), health club, train station, restaurants and a library. 0.6 miles to Harlem Blue Line. Prices are subject to change.