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Holiday 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.

Private Studio in Bridgeport, Chicago
SUPERHOST
Entire guest house · 3 guests · 1 bed · 1 bathroom
Private Studio in Bridgeport, ChicagoA bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.
Polk Street Coach House Apartment, Little Italy/Medical Dist
PLUS
Entire guest house · 6 guests · 2 beds · 1 bathroom
Polk Street Coach House Apartment, Little Italy/Medical DistCook in a kitchen with everything from a KitchenAir convection range and Kitchen Aid food processor to Calphalon pots and pans. The mid-century look includes a comfy American Leather sofa, Gansgo Mobler dining table, and Frem Rolje teak chairs.
Royal Coach House Cottage
SUPERHOST
Entire rental unit · 4 guests · 2 beds · 1 bathroom
Royal Coach House CottageRoyal 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.

Holiday rentals for every style

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Popular amenities for South Side holiday rentals

  • Kitchen
  • Wifi
  • Pool
  • Free parking on premises
  • Air conditioning

Other great holiday rentals in South Side

  1. Entire guest suite
  2. Chicago
Perfect Private Getaway in Perfect Pilsen
₹3,758 per night
SUPERHOST
  1. Private room
  2. Chicago
Restoring Chicago Speakeasy from 1920's Room 1A
₹7,612 per night
  1. Entire rental unit
  2. Chicago
Lovely Entire 1 Bedroom Condo In Hyde Park
₹6,852 per night
SUPERHOST
  1. Private room
  2. Chicago
In the heart of Pilsen, Self Check In
₹3,276 per night
  1. Private room
  2. Chicago
w1 New Queen bed near Downtown Chicago Chinatown
₹3,212 per night
  1. Entire apartment
  2. Chicago
Private Lemon Penthouse near Green Line
₹8,790 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
1-Bedroom Close to Downtown/Chinatown/White Sox
₹3,683 per night
SUPERHOST
  1. Entire loft
  2. Chicago
Artsy Loft Near Downtown
₹6,980 per night
PLUS
  1. Entire residential home
  2. Chicago
Get Cozy at a Powder-Blue Residence in the Heart of Pilsen
₹7,676 per night
SUPERHOST
  1. Entire rental unit
  2. Chicago
Corner heaven 2b/2b w optional parking/sleeps 6
₹14,656 per night
SUPERHOST
  1. Entire apartment
  2. Chicago
420 friendly modern 3BR unit with optional parking
₹11,573 per night
SUPERHOST
  1. Entire townhouse
  2. Chicago
CITY CONDO with GARAGE 7 min Walk to Train
₹4,828 per night