
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.

Live Logan Square The Globally Loved Neighborhood
Discover your serene Logan Square oasis on a quiet cul-de-sac, just steps from Milwaukee Ave’s top restaurants, bars, Maplewood Brewery, Stan Mansion, Rosa’s Blues Lounge & The Whale. Explore the 606 Trail, hop the Blue Line to airports & downtown, Fullerton bus to Lincoln Park Zoo, and Lakefront or stroll to Bucktown, Wicker Park & the public library a block away. Enjoy self-check-in, free street parking, a fully equipped kitchen, 4 BR, 2 BA, washer/dryer & yard. (No parties per Chicago regs.)

Upscale Home in Lincoln Park Minutes from Downtown
Minutes outside downtown Chicago, built in 1890, this gorgeous fully-remodeled modern Victorian-era row house is located in the heart of Chicago’s historic and vibrant Lincoln Park. One of Chicago’s most affluent neighborhoods! > Walkability score of 98/100 > 4 min walk to the train station, steps to bus stops, short Uber ride to all top Chicago attractions > Across DePaul > Amazing parks & bike trails, free zoo, performing arts, shops, nightlife, spas & some of Chicago’s finest restaurants

Hidden Gem - 3 Story House & Pet Friendly!
Cozy & entertaining family -pet friendly property in the heart of Chicago - Lincoln Park. This Smart triplex has a fully-equipped kitchen. Large patio w/ sunset views. 3 bedrooms & 2.5 bathrooms. A Foosball table, 82' TV & BAR to enjoy a night in. This property is perfect to book w/ family or friends. Its spacious yet set up the right way to entertain in one floor, cook in another & sleep without having to deal with noise. Pets: Certain restrictions may apply. It is $35/night per pet

Cozy & Bright Townhome near O’hare -Self Check In-
Escape into this Montclare Masterpiece! Be one of the first guests to enjoy our revitalized, fully-stocked home with attached deck. This 3-level home comes with a spacious, light-flooded living area with attached open kitchen w/ SS appliances, granite countertops/ backsplash, and accent lighting - perfect for larger groups. On the third level you'll find 2 elegant bedrooms with ample closet space, updated full bathroom, and in unit washer and dryer provide all the essentials and more!

Entire House/United Center /Garage-Walk to Train
Entire 3 bedroom - 2 bath townhouse One Garage Parking space & free street parking. Reliable Wi-Fi. WALK TO UNITED CENTER Concerts, Bulls & Blackhawk games. We are 3 miles from Lake Michigan. Blue Line train 7 minute walk or take bus directly across the street to trendy West Loop bars, restaurants & shops. 10-minute ride. 15 to City Center. Please do not book if you smoke. Please agree in message to no smoking and no visitors Only guests on reservation are permitted in the home.

The NICEST place in Evanston for Families 1500Main
Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Upscale 3 bed 1.5 bath near Chicago O'Hare Airport
Free!! Coffee station with 12 types of Keurig pods such as Dunkin/Starbucks/McDonalds/Green tea/Decaf etc. Make your favorite coffee on our commercial brewer. Newly remodeled, luxurious, 3 bedrooms, 1.5 bathrooms duplex house located 10 minutes from O’Hare International Airport. 10-15 minutes from Allstate Arena, Rosemont Convention Center, Fashion Outlets of Chicago and Rivers Casino. Downtown Chicago is 25 minutes away with an easy access to I-94 and I-294 Expressways.

Downtown Oak Park - Luxury 3 bed 3.5 bath Townhome
Entire townhome located in charming downtown Oak Park. Luxury accommodations. Free Parking. Dog friendly. Highly-walkable area. Attached two-car garage. Chicago's El and Metra train stops a short 2-block walk. Both trains bring you to the heart of downtown with the El extending into many Chicago neighborhoods. Shopping, restaurants, Target, Trader Joe's and Frank Lloyd Wright homes within walking distance. TVs logged into Hulu, Disney +, ESPN, Netflix and HBO Max.

Spacious 4BR, central ChinaTown by McCormick/DWNT
Unique 2 story duplex situated in the heart of Chinatown. It’s beautiful, modern and newly furnished 4bedrm/3baths for business conventions and vacation travel. One FREE private parking and plenty of street parking. This home has 8 beds, 2 sofa beds can accommodate 16 or more guests. Walking distance to Ping Tom Park for Water Taxi, Public Transportation, Starbucks, McCormick Place Convention Center, Wintrust Arena. Minutes to Downtown and popular attractions.

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit
This generously sized, quiet apartment, located in the highly sought-after Lincoln Park neighborhood, offers convenient access to acclaimed restaurants and boutiques, all within a five-minute walk. Its private entrance and proximity—less than four blocks—to both the Red and Brown Line "L" stations ensure effortless access to Chicago's attractions, most within a two- to five-stop train ride. Zoned parking permits are provided.

Sanitized Home, 4BR/3BA, Free Parking available
This conveniently located in the heart of Chicago and newly renovated townhouse features 4 bedrooms(1 King bed room, 1 Double bed room, 1 Double bed room and 1 Queen bed + 1 Full sized bed room in basement with curtains blocked), 3 full bathrooms and fully equipped kitchen. Minutes to Downtown, McCormick Place, Chinatown and popular attractions. Walking distance to stores and many great restaurants.

Cheerful 3 story townhouse Old Town/LP
Discover a luxurious three-story townhouse, ideally located for exploring Chicago's Lincoln Park Zoo, Lake Michigan, Magnificent Mile, Old Town, and Lincoln Park's vibrant dining and shopping. Enjoy a complimentary designated parking spot. Please note: due to a host's medical condition, we cannot accommodate service animals that are cats or dogs. A fee applies for more than two guests.
Popular amenities for South Side townhouses
Family-friendly townhouses

Gated 3-Level Apt, Near Hospitals and Downtown

4 bed/1.5 bath townhouse in FLW Historic District!

Game Room | Exercise Area | Firepit | Sanitized

Stylish Chicago Duplex Close to Parks & Dtwn

a SIMPLE place

Bronzeville 10minsDowntown WasherDryer SelfCheckin

𓃥Wicker Cozy Corner w/Parking on site

Great Migration Guest House - Entire Guest House
Townhouse rentals with a washer and dryer

Urban Oasis in Heart of Chicago

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Insta Worthy Prime Spot *Patio *Parking *Fireplace

Townhome Near Munster/Hospital/BP Refinery

Luv Happii House

*Hyde Park *2 Masters *2 Living Rooms *Courtyard

Ideal Lakeview location! Walk to Wrigley, DePaul

Spacious Urban Getaway near Downtown
Townhouses with an outdoor patio

Chicago West Town Row House

A Pleasant Stay in Oak Park

Charming 2 bedroom in peaceful Evanston/pet lovers

Northside Famlynest Lincoln Sq 4BR/1.5BA/2P

Chinatown 3 bedroom with Parking - near McCormick

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Charming & Bright Multilevel Townhome with Parking

Vital Urban: Spa Inspired Retreat
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- Lincoln Park
- Wrigley Field
- Millennium Park
- United Center
- Navy Pier
- Six Flags Great America
- Shedd Aquarium
- 875 North Michigan Avenue
- Humboldt Park
- Guaranteed Rate Field
- Frank Lloyd Wright Home and Studio
- Oak Street Beach
- The Field Museum
- Wicker Park
- Garfield Park Conservatory
- Lincoln Park Zoo
- Brookfield Zoo
- Museum of Science and Industry
- Illinois Beach State Park
- Washington Park Zoo
- Willis Tower
- The Beverly Country Club
- Raging Waves Waterpark
- The 606