Vacation rentals in Cook County

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Top-rated vacation rentals in Cook County

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

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Guest favorite

Loft in Brookfield

4.9 out of 5 average rating, 125 reviews

1920s fully updated unique open artist loft space

True artist living loft space!!! One of a kind space in a safe area of the western suburbs close to the city and easy commute to shops stores. very close to trains buses and expressways. Private parking lot. No unit above or below. Quiet and private spacious updated wide open loft. Hardwood floors throughout forced heat and ac slated steel designer bathroom.. Double oven dishwasher electric cooktop sub zero fridge microwave and toaster oven. Ceiling fans two beds. Can sleep 6 for added cost

Superhost

Apartment in Worth

4.85 out of 5 average rating, 20 reviews

Charming 1-Bedroom in Worth, IL

Welcome to your cozy retreat in Worth, IL! This newly remodeled one-bedroom apartment is perfect for a comfortable and convenient stay. Inside, you’ll find a spacious bedroom with a queen bed, fully equipped kitchen with brand-new stainless-steel appliances, an updated bathroom with modern fixtures, and two Smart TVs and highspeed Wi-Fi. Conveniently situated in the South Suburbs of Chicago near shops, parks, and dining, you’ll also have easy access to major highways and public transportation.

Top guest favorite

Home in Berwyn

4.98 out of 5 average rating, 161 reviews

Retro Modern Bungalow | free parking | fire pit

Experience the city in style at our Retro Modern Bungalow, the perfect pad for up to 4 friends. Featuring two spacious bedrooms—each with a king bed and luxury linens—a propane fire pit and a fully fenced, pup-friendly backyard. Enjoy central HVAC, speedy WiFi, and a dedicated workspace. A pack-n-play crib is available at no cost. Central location just south of Oak Park, 15 mins from Midway airport, and 20 mins from downtown. Park for free in our garage or catch the train a few blocks away.

Guest favorite

Private room in Bolingbrook

4.83 out of 5 average rating, 165 reviews

SUPER MEMORY FOAM BED, EZ smart entry. Cable TV

Enjoy a super sleep on a queen size SUPER LUXURY memory foam bed! Couch, desk & more. Beautiful, safe area , homes built around huge trees that are decades old! Water Park, bating range, shopping, Great BUFFETS and other restaurants near! Free Netfil &Prime, Wi-Fi, Free access to laundry room (for stays 2 or more days) Microwave, fridge, spring water & more outside room. Enjoy sitting in one of the several outdoor seating arrangements either on the balcony or on the ground floor

Top guest favorite

Private room in Woodridge

4.89 out of 5 average rating, 428 reviews

Private floor w/ living rm&office-Private bath 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.

Guest favorite

Apartment in Berwyn

5 out of 5 average rating, 18 reviews

NEW Jade Haven in Berwyn/Riverside

Step into Jade Haven, where tranquility meets modern elegance. This serene one-bedroom, one-bath suite offers a peaceful retreat, inspired by the calming essence of jade. The space features a sleek, airy design with thoughtful touches to make you feel right at home. Fully equipped kitchen, cozy living area, the bedroom invites restful nights, while the spa-like bathroom offers a moment of quiet indulgence. Perfect for a restful getaway or a productive stay.

Top guest favorite

Private room in Alsip

4.88 out of 5 average rating, 252 reviews

Safe clean charming close transportation Viva!

Hello world, The room is called la Dolce room, Inspired by my trip to Italy Rome The rug is like a fancy cake top , dark brown for tiramisu dessert, the walls is the color of cappuccino coffee ice cream, & some art Decour made to put you in sweet dream mode in a queen size bed. A beautiful Clean bathroom with clean linen to refresh your self. Have a second room for office space, to use a desk. Safe parking for your rental, close to the highway

Top guest favorite

Guest suite in Naperville

4.95 out of 5 average rating, 462 reviews

Cozy Lakeview Studio with Private Access

Enjoy luxury and comfort in this cozy lakefront studio with a private entrance, attached to a home where the friendly hosts reside. The studio offers a plush queen bed, a kitchenette with a mini fridge, microwave, induction cooktop, and a full bathroom. Located in one of Naperville’s safest neighborhoods, it’s just moments from cafes, restaurants, markets, and a biking trail, with easy access to I-88.

Superhost

Hotel room in Rosemont

4.89 out of 5 average rating, 369 reviews

Relaxing Standard Room l Free Airport Shuttle

Explore the charming neighborhood of Rosemont just outside our doors. Attractions await you: ✔ Offers a 24-hour front desk, airport transfers, an ATM and free WiFi throughout the property. ✔ Enjoy indoor pool or use the business centre that offers printing, copying and fax services. ✔ Breakfast included. Monday to Friday from 6:30AM to 9:30AM, and on Saturday and Sunday from 7:30AM to 10:30AM.

Guest favorite

Private room in Richton Park

4.85 out of 5 average rating, 264 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.

Top guest favorite

Apartment in Hickory Hills

4.97 out of 5 average rating, 61 reviews

Cozy Guest Suite. Private Entry+ Turo Rental

3600 sqf single family home with a Guest Apartment and private entry on the ground level. Your family will be close to everything when you stay at this centrally-located place. Centrally located off of I294, I55, I57 and I80. Easy to and from travel. In Need of a rental we have 2018 Jeep Grand Cherokee High Altitude at the house and listed Turo.

Superhost

Private room in Des Plaines

4.88 out of 5 average rating, 459 reviews

R2 Cozy getaway room surrounded by nature

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