Townhome holiday rentals in Chicago
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Top-rated townhouse rentals in Chicago
Guests agree: these townhouse rentals are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for townhouse rentals in Chicago
Family-friendly townhouse rentals
Townhouse in Chicago
4.97 out of 5 average rating, 228 reviewsNewly Renovated, Spacious Urban Getaway
15–22 Sep
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
3–10 Oct
Townhouse in Evanston
5.0 out of 5 average rating, 84 reviewsThe NICEST place in Evanston for Families 1500Main
23 Feb – 2 Mar
Townhouse in Chicago
4.82 out of 5 average rating, 89 reviewsBridgeport Home
18–25 Aug
Townhouse in Chicago
4.77 out of 5 average rating, 212 reviewsHistoric Pullman Home-Style Comfort & Great Locale
6–13 Oct
Townhouse in Chicago
4.63 out of 5 average rating, 182 reviewsChicago’s Dickens Place a trendy centralized flat
5–12 Feb
Townhouse in Chicago
4.98 out of 5 average rating, 58 reviewsFamily Friendly Triplex a Short Walk from Wrigley
28 Jun – 5 Jul
Townhouse in Chicago
4.95 out of 5 average rating, 62 reviewsBeautiful Spacious RiverWest Townhome 4-Bed/4-Bath
2–9 Nov
Townhouse accommodation with a washing machine and dryer
Townhouse in Chicago
5.0 out of 5 average rating, 66 reviewsUpscale Home in Lincoln Park Minutes from Downtown
3–10 Dec
Townhouse in Chicago
4.8 out of 5 average rating, 41 reviewsCheerful 3-bedroom townhome in west rogers park!!
14–21 Jul
Townhouse in Chicago
4.93 out of 5 average rating, 28 reviewsUrban Oasis in Heart of Chicago
2–9 Nov
Townhouse in Oak Park
5.0 out of 5 average rating, 27 reviewsOak Park/River Forest Townhouse by Concordia Univ.
20–27 Aug
Townhouse in Chicago
5.0 out of 5 average rating, 26 reviewsChic Townhouse: 2BR, Rooftop, Free Parking, Secure
4–11 Aug
Townhouse in Chicago
5.0 out of 5 average rating, 57 reviewsHidden Gem - 3 Story House & Pet Friendly!
24 Feb – 3 Mar
Townhouse in Chicago
5.0 out of 5 average rating, 15 reviewsNorthside Famlynest Lincoln Sq 4BR/1.5BA/2P
28 Oct – 4 Nov
Townhouse in Gary
4.75 out of 5 average rating, 24 reviewsSpacious Townhouse on the Avenue
31 Jul – 7 Aug
Townhouse rentals with a patio
Townhouse in Chicago
4.96 out of 5 average rating, 54 reviewsCozy & Bright Townhome near O’hare -Self Check In-
13–20 Jul
Townhouse in Evanston
4.79 out of 5 average rating, 39 reviewsCharming cozy pets stay free 2 bedrooms duplex
28 Nov – 5 Dec
Townhouse in Chicago
4.97 out of 5 average rating, 70 reviewsLuxury Townhouse, Entire 2 Bdrm West Town Charmer.
27 May – 3 Jun
Townhouse in Chicago
5.0 out of 5 average rating, 25 reviewsModern Townhome With King Suite & Private Patio
25 Jun – 2 Jul
Townhouse in Chicago
4.96 out of 5 average rating, 92 reviewsUpscale 4-Bedroom Townhouse w/Garage - LOCATION
10–17 Dec
Townhouse in Chicago
4.94 out of 5 average rating, 78 reviewsOld Town/Lincoln Park Luxury Home Garage & Rooftop
3–10 Feb
Townhouse in Des Plaines
4.94 out of 5 average rating, 36 reviewsLuxurious 3 bed 1.5 bath home near O'Hare Airport
25 Nov – 2 Dec
Townhouse in Evanston
4.96 out of 5 average rating, 26 reviewsFamily Friendly Home Near Northwestern Campus
12–19 Jul
Quick stats about townhouse rentals in Chicago
Total rentals
190 properties
Rentals with dedicated workspaces
130 properties have a dedicated workspace
Pet-friendly rentals
50 properties allow pets
Family-friendly rentals
120 properties are a good fit for families
Total number of reviews
12K reviews
Nightly prices starting at
$41 SGD before taxes and fees
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
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