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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Top guest favourite

Private room in Elmhurst

4.99 out of 5 average rating, 217 reviews

Chic Oasis near Downtown Chicago

Open the classic wooden shutters and let in the morning sun at this peaceful abode in the suburbs. The kitchen fridge and small appliances, family room, upstairs laundry, and basement game tables. We enjoy hosting our guests and are happy to help with any information and/or suggestions to make their visit as enjoyable as possible. Located in a quiet suburb, there's a park with tennis courts and a playground within walking distance. A short Uber or taxi ride reaches dozens of excellent restaurants and shops in locations such as the cozy downtown Elmhurst area. We are 10 minutes away from public transportation from Elmhurst to downtown Chicago. If you have a vehicle, parking is inexpensive at the Elmhurst train station. If you do not have a vehicle, we recommend taking Uber or Lyft to the Elmhurst train station. If you are planning to drive into the city of Chicago, we recommend using either SpotHero or ParkWhiz parking apps. We will try to make your stay as comfortable as possible. If you have any special needs or requests, please let us know and we will do our best to accommodate you.

Top guest favourite

Apartment in Chicago

5 out of 5 average rating, 33 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Top guest favourite

Home in Berwyn

4.98 out of 5 average rating, 154 reviews

Retro Modern Bungalow | fire pit | free parking

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] back yard. Enjoy central HVAC, hi-speed 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.

Top guest favourite

Guest suite in Wood Dale

4.91 out of 5 average rating, 506 reviews

The Deer Suite

This is a one bedroom apartment within the home. NOT FOR PARTY No Smoking , ABSOLUTELY No events, parties, or large gatherings. The apartment has a separate entrance from the home main entrance. The apartment also comes with comcast high speed internet. The living room couch can be turned into a double bed, that sleeps two. Large ,shower towels and shampoo included. The apartment includes washer and dryer.The bedroom sleeps two .It is about 30min drive to Downtown-Chicago and15min to O'hare .

Superhost

Apartment in Chicago

4.67 out of 5 average rating, 33 reviews

VlP STUDlO - 3rd FLr

Welcome to our 3rd FLOOR VIP STUDIO!!! Located on the 3rd FLOOR of our charming older building. Designed to provide you the optimal comfort and relaxation after your long day. We realize, we’re not a hotel, ergo we may not be a good fit for all; HOWEVER; :) as you decide to try us out, you will not be disappointed you did!! We’re always available to you, our aim; to leave you happier and more refreshed than when you came. AND OF COURSE OUR REPEAT GUESTS GET AN EXTRA 8% OFF WHEN THEY RETURN!

Guest favourite

Private room in Woodridge

4.87 out of 5 average rating, 504 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

Loft in Chicago

4.99 out of 5 average rating, 111 reviews

Lovely Garden Studio in Chicago

Kick back and relax in this calm, stylish space. Located in historic Bronzeville, our modern studio boasts open-plan living, stylish finishes and plenty of room to accommodate up to 3 guests. Our garden studio is located walking distance to the Green Line station, a 10 minute drive to downtown loop, 15-20 minutes away from Midway Airport, 5 minutes to Lake Michigan, and 5 minutes away from McCormick Place Convention Center, IIT, and Hyde Park/University of Chicago.

Guest favourite

Apartment in Berwyn

5 out of 5 average rating, 6 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 favourite

Guesthouse in Chicago

5 out of 5 average rating, 8 reviews

Andersonville Luxe Pool Escape

Welcome to the only chic, two-story pool house just steps from the heart of Andersonville. Enjoy a full kitchen, queen bed, spa-style bath, washer/dryer, and high-speed Wi-Fi. Outside, unwind in your private heated pool and spa in a tranquil, secure setting shared with the owner. Perfectly located near vibrant shops, dining, and a pleasant walk to the beach, this stylish retreat blends comfort, privacy, and convenience for the ideal city escape.

Guest favourite

Tiny homes in Burr Ridge

4.9 out of 5 average rating, 383 reviews

Less is more! Pet friendly Tiny Home near Chicago!

Less is more--see for yourself how big 250 square feet can really feel! For those who would love to try tiny living and a minimalist lifestyle, this is the perfect getaway. This tiny house has everything you will need to fall in love with tiny living! There is a fenced yard, grass area for furry friends, free parking and is close to hiking trails, restaurants, shops, breweries, bars, and Chicago! Check us out on Insta: @LessIsMore_TinyHome

Apartment in Chicago

5 out of 5 average rating, 4 reviews

Zen's Retreat Beach/Golf, 15 min DT, 1425 sq ft

Discover this renovated historical Chicago bungalow nestled in the cultural South Shore neighborhood. ~ Michelle Obama's childhood home and school are nearby ~ The block is the origin of the Back Alley Jazz community festival ~ Museum of Science & Industry ~ Garden of the Phoenix ~ Nature trails & Beaches ~ Jackson Park Golf Course ~ South Shore Cultural Center ~ Nearby access to bus/train, beaches, and free street parking