
Holiday houses 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

Private room in Chicago
4.84 out of 5 average rating, 49 reviewsYellow Room - South Shore Bungalow

Private room in Chicago
4.65 out of 5 average rating, 34 reviewsPerfect Oasis 4mins walk to University & hospital

Private room in Chicago
4.9 out of 5 average rating, 50 reviewsHyde Park/UC Modern Private Room 2

Private room in Chicago
5 out of 5 average rating, 4 reviewsCondo Living! 5 mins from UChicago/Obama Center

Private room in Chicago
4.84 out of 5 average rating, 38 reviews23rd Pl 4U

Private room in Chicago
4.71 out of 5 average rating, 38 reviewsClean & Simple lovely room (2)
Guest favourite

Private room in Chicago
4.94 out of 5 average rating, 16 reviewsCozy art-filled Hyde Park apt

Private room in Chicago
4.76 out of 5 average rating, 166 reviewsAmazing 1 bed room near downtown unit 2 room # 1
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- South Haven Holiday rentals
- Saugatuck Holiday rentals
- Lake Michigan Beach Holiday rentals
- Evanston Holiday rentals
- New Buffalo Holiday rentals
- Chicago Holiday rentals
- Rentals with lake access South Side
- Waterfront rentals South Side
- Condo rentals South Side
- Rentals with pools South Side
- Rentals with a washing machine and dryer South Side
- House rentals South Side
- Rentals with outdoor seating South Side
- Bed and breakfasts South Side
- Apartment rentals South Side
- Private suite rentals South Side
- Rentals with a hot tub South Side
- Rentals with a fireplace South Side
- Smoking-friendly rentals South Side
- Fitness-friendly rentals South Side
- Rentals with a patio South Side
- Kid-friendly rentals South Side
- Pet-friendly rentals South Side
- Family-friendly rentals South Side
- Rentals with breakfast South Side
- Rentals with an EV charger South Side
- Rentals with a fire pit South Side
- Townhouse rentals South Side
- Rentals with beach access South Side
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Millennium Park
- Wrigley Field
- Navy Pier
- United Center
- Oak Street Beach
- Shedd Aquarium
- Humboldt Park
- Six Flags Great America
- Guaranteed Rate Field
- 875 North Michigan Avenue
- The Field Museum
- Lincoln Park
- Frank Lloyd Wright Home and Studio
- Museum of Science and Industry
- Garfield Park Conservatory
- Willis Tower
- Lincoln Park Zoo
- Brookfield Zoo
- Illinois Beach State Park
- Wicker Park
- Washington Park Zoo
- The 606
- Raging Waves Waterpark
- Flossmoor Golf Club