Townhome vacation rentals in South Side
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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 townhouse rentals
Family-friendly townhouse rentals
Townhouse in Manteno
4.97 out of 5 average rating, 229 reviewsManteno clean 2 king beds great location!
Oct 1 – 8
Townhouse in Chicago
4.97 out of 5 average rating, 229 reviewsNewly Renovated, Spacious Urban Getaway
Oct 9 – 16
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Sep 25 – Oct 2
Townhouse in Old Town
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
Dec 24 – 31
Townhouse in Chicago
4.82 out of 5 average rating, 89 reviewsBridgeport Home
Sep 9 – 16
Townhouse in Evanston
5.0 out of 5 average rating, 86 reviewsThe NICEST place in Evanston for Families 1500Main
Apr 6 – 13
Townhouse in Gary
4.93 out of 5 average rating, 71 reviewsSpacious and Cozy Lakeview Retreat in the Dunes!
Apr 25 – May 2
Townhouse in Gary
4.93 out of 5 average rating, 75 reviewsMiller Beach Nature Get Away in Modern Townhome
Mar 14 – 21
Townhouse rentals with a washer and dryer
Townhouse in Country Club Hills
5.0 out of 5 average rating, 16 reviewsLuv Happii House
Sep 9 – 16
Townhouse in Chicago
4.87 out of 5 average rating, 68 reviewsSanitized Home, 4BR/3BA, Free Parking available
Nov 5 – 12
Townhouse in Portage
5.0 out of 5 average rating, 53 reviewsHome near Indiana Dunes, Lake Michigan, Chicago!
Mar 30 – Apr 6
Townhouse in Oak Park
5.0 out of 5 average rating, 27 reviewsOak Park/River Forest Townhouse by Concordia Univ.
Jul 6 – 13
Townhouse in Chicago
5.0 out of 5 average rating, 66 reviewsUpscale Home in Lincoln Park Minutes from Downtown
Aug 8 – 15
Townhouse in Chicago
4.89 out of 5 average rating, 65 reviewsSpacious 4BR, central ChinaTown by McCormick/DWNT
Dec 1 – 8
Townhouse in Evanston
4.96 out of 5 average rating, 26 reviewsFamily Friendly Home Near Northwestern Campus
Apr 19 – 26
Townhouse in West Town
4.95 out of 5 average rating, 19 reviewsModern Downtown Home with Rooftop and Skyline View
Dec 22 – 29
Townhouse rentals with a patio
Townhouse in Brookfield
4.76 out of 5 average rating, 46 reviewsSunny 2 bedroom townhouse near Brookfield zoo.
Aug 21 – 28
Townhouse in Chicago
4.91 out of 5 average rating, 93 reviewsModern and spacious! 20 mins to ORD, 20 mins DT!
Jan 28 – Feb 4
Townhouse in Belmont Cragin
4.96 out of 5 average rating, 56 reviewsCozy & Bright Townhome near O’hare -Self Check In-
Jul 6 – 13
Townhouse in Chicago
5.0 out of 5 average rating, 19 reviews𓃥Wicker Cozy Corner
Oct 4 – 11
Townhouse in Oak Park
4.91 out of 5 average rating, 78 reviewsDowntown Oak Park - Luxury 3 bed 3.5 bath Townhome
Sep 7 – 14
Townhouse in Chicago
4.9 out of 5 average rating, 29 reviewsLocation! 3 Bed House, parking! Rooftop! Safe area
Sep 21 – 28
Townhouse in Chicago
4.89 out of 5 average rating, 70 reviewsInsta-worthy Townhome w/ King Suite &Rooftop Oasis
Dec 3 – 10
Townhouse in Chicago
4.96 out of 5 average rating, 94 reviewsUpscale 4-Bedroom Townhouse w/Garage - LOCATION
Nov 16 – 23
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