Holiday rentals in South Side

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Top-rated holiday rentals in South Side

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Guest favourite

Rental unit in Chicago

4.9 out of 5 average rating, 169 reviews

Royal Coach House Cottage

Royal Coach House Cottage- Nestled in Bronzeville community and nearby Historic Hyde Park neighborhood that is safe and family oriented. Our space is quite cozy, quaint and ideal for relaxation, peace & quiet. Flower and vegetation garden landscape. Centrally located 1.5 miles from lake front, nearby shopping, movie theater, and restaurants. Seconds from park, walking track and playground. Minutes from downtown and Magnificent Mile. Local transportation accessible including bicycle rental.

Guest favourite

Rental unit in Cicero

4.98 out of 5 average rating, 265 reviews

COZY 2Bdr Apt near MDW, Dwtn, United Ctr, Sox, Hwy

Located on a tranquil city side street, this property is walking distance to numerous restaurants and stores. Enjoy easy access to public transportation, including Metra train, CTA Pink Line, and a direct CTA bus to Midway Airport. Downtown Chicago is a mere 20-minute drive away, with the United Center and Soldier Field just 15 minutes away. Ideal for a quick getaway, an overnight stay before your flight, or an extended work assignment. Unwind on the patio, complete with a fire pit and grill.

Guest favourite

Rental unit in Chicago

4.96 out of 5 average rating, 123 reviews

Cute, Clean, Cozy Apartment in Pilsen

Updated, clean and private apartment in Chicago’s unique Pilsen neighborhood. Located on a quiet, tree-lined street with private entrance, it's the perfect spot to rest after a day of exploring this great neighborhood and city. The apartment has a full kitchen with everything needed to make your morning coffee or prepare a meal. Conveniently located to McCormick Place and many of the city's attractions, including West Loop, downtown, United Center, Grant / Union / Douglass Park and more!

Guest favourite

Home in Chicago

4.89 out of 5 average rating, 113 reviews

Boho Chic Coach House 30Min to downtown W/ Parking

Whether your looking to stay near family or be close to Downtown. This place has it ALL! This coach house is located in Mt greenwood which is one of the safest neighborhoods in the City of Chicago. It is home to many police, firefighters and teachers. Downtown is a quick 30 minute drive and there are also many bars and restaurants in walking distance. The home has been totally renovated and stocked with all the essentials. All you need to do now is pack your bags and enjoy your vacation.

Superhost

Rental unit in Chicago

4.82 out of 5 average rating, 189 reviews

Your brand new Chicago suite (unit 1F)

Come stay in the home of an artist. Enjoy this comfortable eclectic apartment that's filled with great work from local artist. Enjoy the book collection while you relax on the tufted chaise or cozy up to the couch and enjoy netflix. You get the entire apartment to yourself. It has everything you need for a comfortable stay. The neighborhood is very quiet with multiple nearby transportation options. Surrounding neighborhoods just 10 min away offer many restaurant & entertainment options.

Guest favourite

Apartment in Chicago

4.86 out of 5 average rating, 139 reviews

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit suite, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and so much more.

Guest favourite

Rental unit in Chicago

4.81 out of 5 average rating, 103 reviews

Best Location in Hyde Park apartment

Lovely 1 bedroom apartment in Hyde Park location. Within one block of the U of Chicago. The lake is within a 10min walk. Close to the science museum, Metra, restaurants, parks, and famous Japanese garden. Updated unit was remodeled last year for you to enjoy. Separate living/dining rooms. The dinning room has a large table for you to enjoy a meal or get some work done. Great view to the park and tennis courts and porch on the kitchen to enjoy breakfast outside. Parking available.

Guest favourite

Rental unit in Chicago

4.96 out of 5 average rating, 111 reviews

The Photographers' Place

Tina and Kevin are your hosts for this Vintage cozy 600 sq. ft. apartment. 1st floor. Plenty of light. City living in established Bridgeport Neighborhood. Convenient location to McCormick Place (2miles), WinTrust Arena, Downtown, Chinatown, UIC, IIT, Soldier Field and Sox Park for baseball fans. Art, music, restaurant, brewery within walking or short bus ride. Grocery, Walgreens, CVS, Restaurants, Dunkin Donuts, Starbucks, 1 block away. We're only a phone call or text away.

Guest favourite

Loft in Chicago

4.94 out of 5 average rating, 171 reviews

Entire Spacious, Private Loft Apt Historic Beverly

You have the loft suite to yourself. Best for 1 - 2 people Access through the front door & complete privacy with a bathroom and separate entrance (locked doors) in a victorian farmhouse in lovely, tree-lined historic Beverly. Cozy, safe & well stocked with beverages & snacks. We are onsite hosts as we live on the 1st two floors. NOT SUITABLE if you have difficulty with stairs or lots of luggage (3rd floor) Queen bed & two twin beds avail Free street parking

Superhost

Rental unit in Chicago

4.84 out of 5 average rating, 273 reviews

Teeny Tiny Bohemian Lodge - Clean & Affordable

Explore the wonderful neighborhood of Pilsen from this unique little space. Private entrance to your bedroom with an attached bathroom with shower. The entire space is for your private use- nothing is shared. NOTE the bedroom & bathroom ARE the entire space. Designed for one person as a sleeping room. We can not host 2 people. Twin size American bed is 38 x 75 inches. Please CLICK "show more " below BEFORE YOU BOOK/INQUIRE I need you to read and respond.

Superhost

Rental unit in Whiting

4.85 out of 5 average rating, 140 reviews

NEW! |Studio Apartment Whiting IN, United States#2

Welcome to the Charming town of Whiting! The charming town of Whiting is located on the southern shore of Lake Michigan. Whiting is neighbor to Hammond IN & Chicago IL. This space is only 2 minutes away from the skyway with easy access to the city of Chicago & only two blocks down from the Hammond Horseshoe Casino. These newly renovated units also offer a comfortable and convenient stay for those who would like to travel and explore both cities.

Superhost

Guest suite in Chicago

4.86 out of 5 average rating, 267 reviews

Comfy/Private Entry & Bath/Free Parking - Win Win!

A Hidden GEM on a private block in Bronzeville, ranked one of the hottest neighborhoods in Chicago. Great for those looking to travel the city from Downtown (4 miles), to the lake (1 mile) to Hyde Park (walking distance) or those simply looking to stay in and rest in a peaceful place. Welcoming guests from near and far in this comfy studio designed specifically to host those for a great Chicago experience!