Townhome vacation rentals in South Side
Find and book unique townhouse rentals 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 townhouse rentals
Family-friendly townhouse rentals
Townhouse in Chicago
4.75 out of 5 average rating, 224 reviewsHistoric Pullman Home-Rustic Style & Great Locale
Private room in Chicago
4.83 out of 5 average rating, 135 reviewsPrivate Bedroom w/ bath in Chicago Downtown/Loop
Townhouse in Chicago
4.84 out of 5 average rating, 161 reviewsDowntown Elegance ✨ Private Yard Parking
Townhouse in Chicago
4.87 out of 5 average rating, 316 reviewsCITY CONDO with GARAGE 7 min Walk to Train
Private room in Chicago
4.96 out of 5 average rating, 224 reviewsSpacious garden level suite
Townhouse in Chicago
4.6 out of 5 average rating, 192 reviewsChicago’s Dickens Place a trendy centralized flat
Private room in Chicago
4.71 out of 5 average rating, 137 reviewsPrivate Room and Bath in Perfect Location
Townhouse in Chicago
5 out of 5 average rating, 60 reviewsLovely Designer Home RiverWest 4-Bedrooms/4-Bath
Townhouse rentals with a washer and dryer
Townhouse in Chicago
5 out of 5 average rating, 5 reviewsNo Cleaning Fee, Free Parking (with e-Charging)
Townhouse in Chicago
5 out of 5 average rating, 20 reviewsNorthside Famlynest Lincoln Sq 4BR/1.5BA/2P
Townhouse in Chicago
4.86 out of 5 average rating, 101 reviewsModern Downtown Home with 5 Baths & Private Garage
Townhouse in Chicago
4.7 out of 5 average rating, 54 reviewsHistoric Alta Vista Terrace District
Townhouse in Brookfield
4.68 out of 5 average rating, 57 reviewsSunny 2 bedroom townhouse near Brookfield zoo.
Townhouse in Orland Park
5 out of 5 average rating, 6 reviewsLuxurious townhome
Townhouse in Chicago
4.71 out of 5 average rating, 17 reviewsStylish Chicago Duplex Close to Parks & Dtwn
Townhouse in Chicago
4.93 out of 5 average rating, 15 reviewsPulaski Mahal - Spacious “Smart” Home w/Game Room
Townhouse rentals with a patio
Townhouse in Chicago
4.97 out of 5 average rating, 73 reviewsCozy & Bright Townhome near O’hare -Self Check In-
Townhouse in Chicago
4.7 out of 5 average rating, 114 reviewsGreat Location-Lincoln Park/Wrigleyville +Parking!
Townhouse in Chicago
4.91 out of 5 average rating, 23 reviews3-Story,Free Parking,No Pet Fee,Private Patio,W/D
Townhouse in Chicago
4.78 out of 5 average rating, 55 reviewsCharming & Comfy Gem ~ 10 Mins to Downtown ~Patio!
Townhouse in Chicago
5 out of 5 average rating, 24 reviewsChinatown 3 bedroom with Parking - near McCormick
Townhouse in Chicago
5 out of 5 average rating, 39 reviewsModern Townhome With King Suite & Private Patio
Townhouse in Chicago
4.92 out of 5 average rating, 12 reviewsLux Full House: Outdoor Paradise + FREE Parking!
Townhouse in Chicago
4.9 out of 5 average rating, 98 reviewsLincoln Park, Rooftop-Your Insta-Perfect Getaway!
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Evanston Vacation rentals
- Saugatuck Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Bend Vacation rentals
- Schaumburg Vacation rentals
- New Buffalo Vacation rentals
- Chicago Vacation rentals
- Townhouse rentals United States
- House rentals United States
- House rentals Chicago
- Townhouse rentals Chicago
- House rentals Chicago
- Townhouse rentals Chicago
- House rentals Downtown Chicago
- Townhouse rentals Downtown Chicago
- Condo rentals South Side
- Rentals with breakfast South Side
- Private suite rentals South Side
- Bed and breakfasts South Side
- Family-friendly rentals South Side
- Rentals with a washer and dryer South Side
- Pet-friendly rentals South Side
- Rentals with pools South Side
- Rentals with an EV charger South Side
- Rentals with outdoor seating South Side
- Waterfront rentals South Side
- Monthly Rentals South Side
- Smoking-friendly rentals South Side
- Rentals with a fireplace South Side
- Apartment rentals South Side
- Fitness-friendly rentals South Side
- Rentals with lake access South Side
- Rentals with beach access South Side
- House rentals South Side
- Rentals with a fire pit South Side
- Rentals with a hot tub South Side
- Rentals with a patio South Side
- Kid-friendly rentals South Side
- House rentals Milwaukee
- Townhouse rentals Illinois
- House rentals Illinois
- Townhouse rentals Cook County
- House rentals Cook County
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom