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Vacation rentals in South Side

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Top-rated holiday rentals in South Side

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

Guest favourite
Apartment in Chicago
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.
20 – 27 Oct
Guest favourite
Condo in Chicago
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.
23 – 30 Apr
Superhost
Apartment in Woodlawn
University Retreat
Lovely 3 bedroom apartment in Hyde Park location. Within one block of the U of Chicago; close to the science museum, Metra, restaurants, parks, and less than 1 mile from the proposed Obama Library and the lake. Updated unit has nearly 1,300 SF of livable space to enjoy: vintage hardwood floors throughout, separate living/dining rooms, kitchen with new stainless steel appliances, new furnace, new hot water tank, and a new porch with large fenced yard. Permit parking for guests only!
24 – 31 July

Popular amenities for South Side holiday rentals

Other great holiday rentals in South Side

Guest favourite
Apartment in Chicago
Amazing Location | Stunning Views | Free Parking
4 – 11 Feb
Guest favourite
Guest suite in Bronzeville
Bronzeville Beauty: Modern Style + Historic Charm
1 – 8 Aug
Guest favourite
Condo in Woodlawn
A Stones Throw from U Chicago South Campus!
17 – 24 Oct
Guest favourite
Apartment in Pilsen Historic District
Modern
28 Mar – 4 Apr
Superhost
Apartment in Chicago
The Cottage
Guest favourite
Home in Pilsen Historic District
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
30 Nov – 7 Dec
Guest favourite
Holiday home in South Shore
UChicago Luxurious King Suite Lakefront
2 – 9 Nov
Superhost
Apartment in Chicago
Your Oasis of Elegance in Greater Grand Crossing
12 – 19 May
Guest favourite
Apartment in Chicago
Ground-Level Speakeasy: 1BR-1.5BA Near Everything!
2 – 9 May
Superhost
Guest suite in Bronzeville
Bronzeville Guest Suite - 1 Br
28 June – 5 July
Superhost
Apartment in Woodlawn
Eclipse: Modern Apt. in Woodlawn
2 – 9 Feb
Guest favourite
Apartment in Chicago
Location! Location! Location!
10 – 17 May

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