
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.
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Holiday rentals for every style
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Popular amenities for South Side holiday rentals
Other great holiday rentals in South Side
Guest favourite

Private room in Chicago
4.91 out of 5 average rating, 35 reviewsHyde Park/Kenwood close to UChicago Hospital. Bike
Superhost

Private room in Chicago
4.75 out of 5 average rating, 64 reviewsPrivate room, Near IIT, McCormick, free parking5
Guest favourite

Private room in Chicago
4.85 out of 5 average rating, 40 reviewsB: Spacious bedroom with private workspace.
Top guest favourite

Private room in Chicago
5 out of 5 average rating, 91 reviewsHistoric campus U of C Prof. mansion, top location
Guest favourite

Private room in Chicago
5 out of 5 average rating, 30 reviewsPrivate bath Hyde Park UChicago x2

Private room in Chicago
4.59 out of 5 average rating, 63 reviewsPink Room - SouthShoreBungalowLower FL SomeHumming
Top guest favourite

Private room in Chicago
4.99 out of 5 average rating, 257 reviewsHyde Park - Walk to University of Chicago
Guest favourite

Private room in Chicago
4.82 out of 5 average rating, 17 reviewsTwinning & Winning - Yellow Key - Place 2
Destinations to explore
- Chicago Holiday rentals
- Indianapolis Holiday rentals
- Downtown Chicago Holiday rentals
- Platteville Holiday rentals
- St. Louis Holiday rentals
- Detroit Holiday rentals
- Columbus Holiday rentals
- Louisville Holiday rentals
- Southern Indiana Holiday rentals
- Cincinnati Holiday rentals
- Milwaukee Holiday rentals
- Wisconsin River Holiday rentals
- Family-friendly rentals South Side
- Bed and breakfasts South Side
- Rentals with a fireplace South Side
- Rentals with a washing machine and dryer South Side
- Rentals with a patio South Side
- Rentals with outdoor seating South Side
- Rentals with an EV charger South Side
- Pet-friendly rentals South Side
- Flat rentals South Side
- Rentals with breakfast South Side
- House rentals South Side
- Townhouse rentals South Side
- Waterfront rentals South Side
- Rentals with lake access South Side
- Rentals with beach access South Side
- Rentals with a hot tub South Side
- Smoking-friendly rentals South Side
- Private suite rentals South Side
- Apartment rentals South Side
- Fitness-friendly rentals South Side
- Rentals with pools South Side
- Rentals with a firepit South Side
- Lincoln Park
- Millennium Park
- Wrigley Field
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- Humboldt Park
- Guaranteed Rate Field
- 875 North Michigan Avenue
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Illinois Beach State Park
- Wicker Park
- Garfield Park Conservatory
- Washington Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Lincoln Park Zoo
- Willis Tower
- Raging Waves Waterpark
- The 606
- The Beverly Country Club