Townhome vacation rentals in South Side

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Top-rated townhouse rentals in South Side

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Guest favorite

Townhouse in Chicago

4.98 out of 5 average rating, 229 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

The newly renovated spacious apartment is furnished with brand new modern king bed in the bedroom to ensure restful nights. In large living room, beautiful cherry dining table to enjoy morning coffee and comfortable L-shape leather sofa for watching your favorite movies from Netflix on 43" flat screen TV. The brand new fully equipped kitchen has a granite countertops, stainless steel appliances. The modern marble bathroom has a huge mirror over the sink, glass sliding shower doors, a full size bath tub and a hair dryer. Spacious 3 room apartment with all the amenities specified above is for guests use only and free residential parking permits provided upon request. I'm always available. I live on the 2nd floor of the townhouse with my husband and work at a bridal boutique which I own on west Armitage Ave. The apartment is super conveniently located in the Armitage/Sheffield. It's 2 1/2 blocks or 5 minutes walk to both Brown and Red line stations which make getting around Chicago fast and easy. Visiting lake front Millennium Park takes less than 20 minutes from the apartment. My neighborhood is surrounded by Old Town, full of local shops and restaurants, Wrigley Field, eclectic Bucktown shops, and the Lincoln Park Zoo. The 3 Michelin-starred restaurant, Alinea is 2-minute walk from the door. Take either Red ( North/Clybourn ) or Brown (Armitage/Sheffield ) line for exploring Rush st( 1 stop) Water Tower, Michigan Ave, Mag miles, Gold Coast( 2 stops ) The Navy Pier( 3 stops) Millennium Park, Cloud Gate/ The Bean, Buckingham Fountain, Art Institute of Chicago,( 4stops). Both stations are within 5 min walking distance from the apartment. It's also a short cab or Uber ride to Michigan Ave. Gold Coast. No smoking, no street shoes, no parties allowed. The nightly rates are for 2 guests only and $25 guest fee applys for 3rd guest. There is a $500.00 penalty for breaking the each rule.

Jan 5 – 12

ﺩ.ﺇ784 per night

Superhost

Townhouse in Chicago

4.87 out of 5 average rating, 141 reviews

⭐️Cozy Garden Unit by Downtown & Blue Line Stop⭐️

Cozy, comfy garden apartment that sleeps up to 4 people with access to the patio w/ fire pit and rooftop deck. Located right next to the underground train stop. A quick trip to Downtown & hip Wicker Park/Logan dining, shopping & nightlife. A straight shot from ORD on the Blue line Normal check-in is 4 pm. Bag drops possible as early as noon. I will notify you if an early check-in is possible on the day of arrival. Please be flexible with check-in times if booking with less than 24 hours’ notice

Aug 6 – 13

ﺩ.ﺇ579 per night

Guest favorite

Townhouse in Portage

4.98 out of 5 average rating, 54 reviews

Home near Indiana Dunes, Lake Michigan, Chicago!

Enjoy home away from home in this beautiful two bedroom, THREE beds, one bath home with plenty of living room and kitchen sunlight . Relax in a comfortable living room with recliner chairs while you enjoy a warm cup of coffee or your beverage of choice.Home has plenty of parking including a driveway for two cars and free street parking. If you enjoy the outdoors, you'll love our extra large back yard! Enjoy a short walk down the block to a beautiful trail and enjoy winter sledding and disc golf.

Jan 31 – Feb 7

ﺩ.ﺇ318 per night

Guest favorite

Townhouse in Chicago

4.93 out of 5 average rating, 187 reviews

A Cozy Oasis - Guest Favorite Logan Square Chicago

On a quiet cul-de-sac in Logan Square, this home is a serene oasis. Steps away from Milwaukee Ave's renowned restaurants, bars, Revolution Brewery, Stan Mansion, and The Whale, 606 trail, Blue Line to airports and downtown, as well as Bucktown and Wicker Park. Logan Square Public Library is a block away. Enjoy a self-check-in process, free street parking, fully equipped kitchen, 3 BR, 1 bath, and amenities like a washer, dryer, and yard. Please note, Per Chicago regulations, no parties allowed.

Mar 20 – 27

ﺩ.ﺇ755 per night

Guest favorite

Townhouse in Chicago

4.86 out of 5 average rating, 43 reviews

Large Executive Row house in Historic Pullman

Charming well appointed home w/exquisite furnishings. Safe, family friendly neighborhood w/shopping nearby. Walking distance to train station. Private entrance w/large rooms & plenty of space to host larger groups. We have everything from soaps to seasonings. Top quality new beds mattresses & linens. Walk to Pullman National Monument with visitors center staffed by US Park Rangers that feature state of the art interactive exhibits that appeal to all ages. Guided walking tours available.

Apr 24 – May 1

ﺩ.ﺇ482 per night

Guest favorite

Townhouse in Chicago

5.0 out of 5 average rating, 26 reviews

Chic Townhouse: 2BR, Rooftop, Free Parking, Secure

Welcome to our luxurious 2-bedroom, 2-bathroom townhouse located in the heart of south loop Chicago! Our home is perfect for travelers who desire being in close proximity to all the city's major tourist attractions. Enjoy breathtaking views of the city from our rooftop terrace, where you can relax and unwind after a day of exploring. Our secure complex ensures your safety and peace of mind throughout your stay, while free parking provides a hassle-free experience for those traveling by car.

Oct 18 – 25

ﺩ.ﺇ1,624 per night

Superhost

Townhouse in Brookfield

4.76 out of 5 average rating, 46 reviews

Sunny 2 bedroom townhouse near Brookfield zoo.

2 bedroom, 2 floor (bathroom on 2nd level), pet friendly, townhouse in the heart of Brookfield; 5 minutes from Brookfield zoo; 1 block from downtown Brookfield with a good selection of bars and restaurants; 5 minutes from downtown La Grange; 1 block from metra station and equal distance from O'hare and Midway airports. 1 parking space on back patio (if additional parking is needed I can submit a request for permit parking on street please provide vehicle license plate, make & model).

Sep 6 – 13

ﺩ.ﺇ468 per night

Superhost

Townhouse in Chicago

4.93 out of 5 average rating, 28 reviews

Urban Oasis in Heart of Chicago

Modern townhome built 2020 with easy access to 18th St restaurants, Fulton Market & Downtown via Pink Line train (0.5 mile). First floor MASTER SUITE, 3 beds (1 queen, 2 full), 2.5 baths, laundry in-unit, fully-stocked kitchen, & FREE PARKING off-street. Heart of Chicago is a quiet, incredibly well-preserved area at the edge of Chicago’s hip Pilsen neighborhood, brimming w/ original 1880s vintage character & unique architectural charm, + the best Italian & Mexican food in Chicago!

Jun 23 – 30

ﺩ.ﺇ881 per night

Guest favorite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 294 reviews

a SIMPLE place

Booking the entire house with 100% privacy. It has 2 driveway parking spaces and street parking. Garage may be available. CHECK-IN and OUT are flexible. I set checkout at 11am (text me if you need late checkout). The space is perfect for a family of 4. It is located about 20 minutes from O'Hare airport and 40 minutes from Chicago downtown. Infants and pets are welcome (please text me for over size pets or more than 2 pets) Play pan is available upon request.

Jan 6 – 13

ﺩ.ﺇ365 per night

Guest favorite

Townhouse in Chicago

5.0 out of 5 average rating, 5 reviews

Chinatown 3 bedroom with Parking - near McCormick

Welcome to our new townhome offering in Chinatown. This 3-story home has 4 queen beds to accommodate 8+ guests. An outdoor private parking space is included with plenty of street parking too. You're right in the middle of THE Chicago foodies destination with more than 30+ restaurants all within walking distance. Minutes to Downtown, McCormick Place, Ping Tom Park, UIC, public transit, convenience store, Starbucks and many popular attractions.

Oct 16 – 23

ﺩ.ﺇ1,377 per night

Guest favorite

Townhouse in Chicago

4.85 out of 5 average rating, 275 reviews

CITY CONDO with GARAGE 7 min Walk to Train

Experienced Super-host offers private spacious & sunny condo 3 miles from Chicago "Loop" Lakefront and Museums. Large one bedroom with king size premium mattress, and full sized sofa-bed sleeps 4. 1 FREE garage PARKING wi-fi , washer & dryer. BUS to city center is across the street. 10 minute ride to city center. Walk to United Center Bulls/Blackhawk games /concerts and large international grocery store. Note- WE DO NOT HOST SMOKERS.

Nov 3 – 10

ﺩ.ﺇ374 per night

Guest favorite

Townhouse in Country Club Hills

5.0 out of 5 average rating, 16 reviews

Luv Happii House

Truly enjoy home away from home at the Luv Happii House, a Charming, vintage style canna friendly townhouse. Perfect for a weekend getaway, business trip, work from home alternative, content creation, or cozy home base while exploring everything Chicago and the South Suburbs of Chicago have to offer including nearby The Credit Union 1 Amphitheater and Tinley Park Convention Center.

Sep 9 – 16

ﺩ.ﺇ682 per night