Townhome holiday rentals in South Side

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Top-rated townhouse rentals in South Side

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Guest favourite

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.

18–25 Nov

₹17,761 per night

Superhost

Townhouse in West Town

4.86 out of 5 average rating, 142 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

6–13 Aug

₹13,097 per night

Guest favourite

Townhouse in Chicago

4.93 out of 5 average rating, 188 reviews

Cozy Oasis Top Guest Reviews 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.

16–23 Oct

₹14,916 per night

Superhost

Townhouse in Magnificent Mile

4.8 out of 5 average rating, 157 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also those who fancy a beach in the City!

17–24 Nov

₹48,453 per night

Guest favourite

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.

9–16 Jun

₹14,960 per night

Superhost

Townhouse in Brookfield

4.77 out of 5 average rating, 47 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).

20–27 Oct

₹10,639 per night

Guest favourite

Townhouse in Chicago

4.91 out of 5 average rating, 74 reviews

Enjoy Chicago/suburbs 2BR townhouse fully equipped

Imagine yourself in the heart of Chicago, just minutes away from the charming suburbs. Picture strolling through Oak Park, the hometown of Hemingway, with its vibrant downtown, tempting eateries in Elmwood Park, Forest Park's allure, and the hidden gems of River Grove. Feel the excitement as you walk to the Metra station, your gateway to downtown Chicago. Don't miss out on this captivating experience—book your stay now and immerse yourself in the vibrant tapestry of the Windy City.

8–15 Nov

₹16,872 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!

23–30 Jun

₹20,015 per night

Guest favourite

Townhouse in Hoffman Estates

4.91 out of 5 average rating, 295 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.

18–25 Apr

₹8,283 per night

Guest favourite

Townhouse in Chinatown

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.

13–20 Dec

₹27,520 per night

Guest favourite

Townhouse in Chicago

4.85 out of 5 average rating, 278 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.

3–10 Nov

₹8,501 per night

Guest favourite

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.

12–19 Jan

₹14,353 per night