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
5.0 out of 5 average rating, 209 reviewsSpacious 4-Level/4-Bedroom Townhouse in West Loop
Jan 7 – 14
Townhouse in Chicago
4.97 out of 5 average rating, 228 reviewsNewly Renovated, Spacious Urban Getaway
Jul 14 – 21
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Oct 3 – 10
Townhouse in Chicago
4.82 out of 5 average rating, 89 reviewsBridgeport Home
Aug 19 – 26
Townhouse in Evanston
5.0 out of 5 average rating, 84 reviewsThe NICEST place in Evanston for Families 1500Main
Feb 23 – Mar 2
Townhouse in Gary
4.93 out of 5 average rating, 71 reviewsSpacious and Cozy Lakeview Retreat in the Dunes!
Jul 11 – 18
Townhouse in Gary
4.93 out of 5 average rating, 75 reviewsMiller Beach Nature Get Away in Modern Townhome
Dec 2 – 9
Townhouse in Chicago
4.77 out of 5 average rating, 212 reviewsHistoric Pullman Home-Style Comfort & Great Locale
Apr 6 – 13
Townhouse rentals with a washer and dryer
Townhouse in Chicago
4.92 out of 5 average rating, 71 reviewsEnjoy Chicago/suburbs 2BR townhouse fully equipped
Sep 3 – 10
Townhouse in Chicago
5.0 out of 5 average rating, 66 reviewsUpscale Home in Lincoln Park Minutes from Downtown
Jan 1 – 8
Townhouse in Chicago
4.87 out of 5 average rating, 67 reviewsSanitized Home, 4BR/3BA, Free Parking available
Sep 29 – Oct 6
Townhouse in Chicago
4.8 out of 5 average rating, 41 reviewsCheerful 3-bedroom townhome in west rogers park!!
Jul 15 – 22
Townhouse in Chicago
4.89 out of 5 average rating, 65 reviewsSpacious 4BR, central ChinaTown by McCormick/DWNT
Dec 26 – Jan 2
Townhouse in Oak Park
5.0 out of 5 average rating, 27 reviewsOak Park/River Forest Townhouse by Concordia Univ.
Jul 4 – 11
Townhouse in Gary
4.75 out of 5 average rating, 24 reviewsSpacious Townhouse on the Avenue
Jun 26 – Jul 3
Townhouse in Chicago
4.75 out of 5 average rating, 12 reviewsHouse of KAT Properties
Nov 1 – 8
Townhouse rentals with a patio
Townhouse in Chicago
5.0 out of 5 average rating, 4 reviewsChinatown 3 bedroom with Parking - near McCormick
Nov 2 – 9
Townhouse in Chicago
4.91 out of 5 average rating, 93 reviewsModern and spacious! 20 mins to ORD, 20 mins DT!
Mar 6 – 13
Townhouse in Chicago
4.96 out of 5 average rating, 54 reviewsCozy & Bright Townhome near O’hare -Self Check In-
May 27 – Jun 3
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
4.89 out of 5 average rating, 28 reviewsLocation! 3 Bed House, parking! Rooftop! Safe area
Jul 11 – 18
Townhouse in Chicago
4.88 out of 5 average rating, 68 reviewsInsta-worthy Townhome w/ King Suite &Rooftop Oasis
Dec 3 – 10
Townhouse in Chicago
4.97 out of 5 average rating, 70 reviewsLuxury Townhouse, Entire 2 Bdrm West Town Charmer.
May 27 – Jun 3
Townhouse in Chicago
5.0 out of 5 average rating, 25 reviewsModern Townhome With King Suite & Private Patio
Jun 25 – Jul 2
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- Family travel hub Tips and inspiration
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