Townhome vacation rentals in South Side
Find and book unique townhouses on Airbnb
Top-rated townhouse rentals in South Side
Guests agree: these townhouse rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you.
Popular amenities for South Side townhouses
Family-friendly townhouses
Townhouse in Chicago
4.97 out of 5 average rating, 230 reviewsNewly Renovated, Spacious Urban Getaway
Townhouse in Chicago
5.0 out of 5 average rating, 212 reviewsSpacious 4-Level/4-Bedroom Townhouse in West Loop
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Townhouse in Old Town
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
Townhouse in Chicago
4.82 out of 5 average rating, 89 reviewsBridgeport Home
Townhouse in Evanston
5.0 out of 5 average rating, 86 reviewsThe NICEST place in Evanston for Families 1500Main
Townhouse in Gary
4.93 out of 5 average rating, 71 reviewsSpacious and Cozy Lakeview Retreat in the Dunes!
Townhouse in Chicago
4.77 out of 5 average rating, 213 reviewsHistoric Pullman Home-Style Comfort & Great Locale
Townhouse rentals with a washer and dryer
Townhouse in Chicago
5.0 out of 5 average rating, 26 reviewsChic Townhouse: 2BR, Rooftop, Free Parking, Secure
Townhouse in Chicago
4.86 out of 5 average rating, 69 reviewsSanitized Home, 4BR/3BA, Free Parking available
Townhouse in Chicago
5.0 out of 5 average rating, 67 reviewsUpscale Home in Lincoln Park Minutes from Downtown
Townhouse in Oak Park
5.0 out of 5 average rating, 27 reviewsOak Park/River Forest Townhouse by Concordia Univ.
Townhouse in Chicago
4.89 out of 5 average rating, 65 reviewsSpacious 4BR, central ChinaTown by McCormick/DWNT
Townhouse in Chicago
5.0 out of 5 average rating, 12 reviewsLuxurious Wicker Park Home with Parking
Townhouse in Chicago
5.0 out of 5 average rating, 6 reviewsLux Full House +outdoor paradise +FREE parking
Townhouse in Des Plaines
4.95 out of 5 average rating, 39 reviewsLuxurious 3 bed 1.5 bath home near O'Hare Airport
Townhouses with an outdoor patio
Townhouse in Chicago
4.91 out of 5 average rating, 94 reviewsModern and spacious! 20 mins to ORD, 20 mins DT!
Townhouse in Chicago
5.0 out of 5 average rating, 20 reviews𓃥Wicker Cozy Corner
Townhouse in Belmont Cragin
4.96 out of 5 average rating, 56 reviewsCozy & Bright Townhome near O’hare -Self Check In-
Townhouse in Oak Park
4.91 out of 5 average rating, 78 reviewsDowntown Oak Park - Luxury 3 bed 3.5 bath Townhome
Townhouse in Chicago
5.0 out of 5 average rating, 27 reviewsModern Townhome With King Suite & Private Patio
Townhouse in Chicago
4.9 out of 5 average rating, 29 reviewsLocation! 3 Bed House, parking! Rooftop! Safe area
Townhouse in Chicago
4.89 out of 5 average rating, 70 reviewsInsta-worthy Townhome w/ King Suite &Rooftop Oasis
Townhouse in Chicago
4.96 out of 5 average rating, 94 reviewsUpscale 4-Bedroom Townhouse w/Garage - LOCATION
Destinations to explore
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