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
Guest favourite
Apartment in Chicago
4.84 out of 5 average rating, 166 reviewsYour brand new Chicago suite (unit 1F)
Superhost
Apartment in Chicago
4.84 out of 5 average rating, 177 reviewsThe Cottage
Guest favourite
Apartment in Pilsen Historic District
4.89 out of 5 average rating, 247 reviewsModern
Guest favourite
Condo in Chicago
4.9 out of 5 average rating, 193 reviewsA Stones Throw from U Chicago South Campus!
Guest favourite
Apartment in Bridgeport
4.89 out of 5 average rating, 301 reviewsVintage Bridgeport Apartment
Guest favourite
Guest suite in Chicago
4.93 out of 5 average rating, 40 reviewsClassic Den @ U Chicago
Guest favourite
Home in Chicago
4.91 out of 5 average rating, 90 reviewsBoho Chic Coach House 30Min to downtown W/ Parking
Guest favourite
Apartment in Chicago
5.0 out of 5 average rating, 29 reviewsTravel To Chicago New City
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Accommodation & holiday rentals
- Lake Michigan Beach Accommodation & holiday rentals
- Saugatuck Accommodation & holiday rentals
- Evanston Accommodation & holiday rentals
- South Haven Holiday rentals
- Naperville Accommodation & holiday rentals
- South Bend Accommodation & holiday rentals
- New Buffalo Holiday rentals
- Schaumburg Accommodation & holiday rentals
- Chicago Accommodation & holiday rentals
- Private suite rentals South Side
- Family-friendly rentals South Side
- Rentals with outdoor seating South Side
- Rentals with a washing machine and dryer South Side
- Rentals with a fireplace South Side
- Rentals with lake access South Side
- Waterfront rentals South Side
- Smoking-friendly rentals South Side
- Condo rentals South Side
- Rentals with breakfast South Side
- Apartment rentals South Side
- Kid-friendly rentals South Side
- Rentals with pools South Side
- Rentals with a fire pit South Side
- Rentals with a patio South Side
- Townhouse rentals South Side
- House rentals South Side
- Rentals with beach access South Side
- Fitness-friendly rentals South Side
- Rentals with a hot tub South Side
- Monthly Rentals South Side
- Pet-friendly rentals South Side
- Rentals with an EV charger South Side
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