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 Chicago
4.97 out of 5 average rating, 228 reviewsNewly Renovated, Spacious Urban Getaway
Sep 2 – 9
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 Chicago
4.82 out of 5 average rating, 89 reviewsBridgeport Home
Jun 29 – Jul 6
Townhouse in Evanston
5.0 out of 5 average rating, 85 reviewsThe NICEST place in Evanston for Families 1500Main
Mar 3 – 10
Townhouse in Gary
4.93 out of 5 average rating, 71 reviewsSpacious and Cozy Lakeview Retreat in the Dunes!
Dec 10 – 17
Townhouse in Gary
4.93 out of 5 average rating, 75 reviewsMiller Beach Nature Get Away in Modern Townhome
Dec 7 – 14
Townhouse in Chicago
4.77 out of 5 average rating, 212 reviewsHistoric Pullman Home-Style Comfort & Great Locale
Oct 30 – Nov 6
Townhouse in Chicago
4.63 out of 5 average rating, 182 reviewsChicago’s Dickens Place a trendy centralized flat
Jan 27 – Feb 3
Townhouse rentals with a washer and dryer
Townhouse in Chicago
4.87 out of 5 average rating, 68 reviewsSanitized Home, 4BR/3BA, Free Parking available
Oct 1 – 8
Townhouse in Chicago
4.9 out of 5 average rating, 73 reviewsEnjoy Chicago/suburbs 2BR townhouse fully equipped
Apr 1 – 8
Townhouse in Oak Park
5.0 out of 5 average rating, 27 reviewsOak Park/River Forest Townhouse by Concordia Univ.
Jul 9 – 16
Townhouse in Chicago
5.0 out of 5 average rating, 66 reviewsUpscale Home in Lincoln Park Minutes from Downtown
Oct 14 – 21
Townhouse in Chicago
4.89 out of 5 average rating, 65 reviewsSpacious 4BR, central ChinaTown by McCormick/DWNT
Dec 6 – 13
Townhouse in Des Plaines
4.95 out of 5 average rating, 37 reviewsLuxurious 3 bed 1.5 bath home near O'Hare Airport
Sep 5 – 12
Townhouse in Chicago
4.8 out of 5 average rating, 41 reviewsCheerful 3-bedroom townhome in west rogers park!!
Jul 19 – 26
Townhouse in Chicago
4.87 out of 5 average rating, 62 reviewsGreat Location-Lincoln Park/Wrigleyville +Parking!
Jul 25 – Aug 1
Townhouse rentals with a patio
Townhouse in Chicago
4.96 out of 5 average rating, 56 reviewsCozy & Bright Townhome near O’hare -Self Check In-
Jul 6 – 13
Townhouse in Chicago
4.91 out of 5 average rating, 93 reviewsModern and spacious! 20 mins to ORD, 20 mins DT!
Nov 26 – Dec 3
Townhouse in Chicago
5.0 out of 5 average rating, 17 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 2 – 9
Townhouse in Chicago
4.88 out of 5 average rating, 69 reviewsInsta-worthy Townhome w/ King Suite &Rooftop Oasis
Dec 3 – 10
Townhouse in Chicago
4.89 out of 5 average rating, 28 reviewsLocation! 3 Bed House, parking! Rooftop! Safe area
Oct 15 – 22
Townhouse in Chicago
5.0 out of 5 average rating, 26 reviewsModern Townhome With King Suite & Private Patio
Sep 4 – 11
Townhouse in Chicago
4.97 out of 5 average rating, 71 reviewsLuxury Townhouse, Entire 2 Bdrm West Town Charmer.
May 27 – Jun 3
Destinations to explore
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