Townhouse holiday rentals in South Side

4.93 out of 5 average rating, 149 reviews

Chic Lincoln Park Townhome | Rooftop + Glam Bar

Welcome to The Lucky Penny! ⭐️ Lincoln Park Luxury | Rooftop + Glam Station | Sleeps 10 ⭐️ Stay in the heart of Lincoln Park, one of Chicago’s most vibrant neighborhoods, where tree-lined streets meet world-class dining, shopping, nightlife, and the lakefront. This beautifully curated 3-story townhome blends luxury, comfort & style, making it ideal for bachelorette weekends, girls’ trips, family stays, and celebratory group getaways. 📍 Steps from Lincoln Park Zoo, cafés, boutiques & lakefront

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An outdoor terrace features comfortable lounge seating and a grill. A panoramic view of the Chicago skyline is visible, showcasing various architectural styles and buildings under a clear blue sky.

4.99 out of 5 average rating, 285 reviews

HUGE 4BR Townhouse FultonMarket/WestLoop!

Stay in a spacious 4-story townhouse in Chicago's vibrant West Loop/Fulton Market, just steps from Restaurant Row, award-winning restaurants, nightlife, coffee shops, parks, and grocery stores. Enjoy the excitement of the neighborhood while staying on a quiet, treelined street for a peaceful night's sleep.Features include a private rooftop terrace with skyline views, an attached garage (1 regular vehicle fits), and easy access to public transit for O'Hare, downtown, Navy Pier, Mag Mile and more.

LocationFamilyWalkability

A spacious living area features a light blue couch with patterned pillows, paired with a cream armchair. Light wood floors extend throughout, creating a warm ambiance. A dining area is visible in the background, highlighted by a chandelier and a decorative wall with exposed brick.

4.87 out of 5 average rating, 304 reviews

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.)

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A bright living room features two light-colored sofas arranged around a coffee table. A large artwork adorns the wall above a decorative fireplace, complemented by elegant sconces. Natural light streams through two large windows with black shutters, enhancing the room's open ambiance.

4.98 out of 5 average rating, 165 reviews

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

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The townhouse stands elegantly among lush greenery, featuring a classic facade with black-framed windows and a welcoming entrance. A wrought-iron fence complements the landscaped front area, while a tree provides shade along the sidewalk.

4.82 out of 5 average rating, 249 reviews

Historic luxury townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the lavish Gold Coast of Chicago—one of the most sought-after locations in the city! Located on one of Chicago’s famous streets, you’ll be a 5-minute walk from the historic Gold Coast beach and intimate views of Lake Michigan. The property is also within walking distance of the subway, where you can connect to the L trains, and the Magnificent Mile. It is the perfect place to stay for adventurous travellers and those who fancy a beach in the City!

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A spacious living area features a comfortable gray sectional sofa adorned with light-colored throw pillows, set against a backdrop of large windows draped with sheer curtains. A round dining table with gray chairs and a sleek kitchen area are visible, creating an inviting open space.

4.98 out of 5 average rating, 121 reviews

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!

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A contemporary living space features a comfortable gray sofa adorned with pillows and a cozy throw. A dining table is set for four, with white plates and light floral arrangements. Large windows with sheer curtains allow natural light to brighten the room.

4.98 out of 5 average rating, 151 reviews

𓃥Wicker Cozy Corner w/Parking on site

Welcome to our charming Wicker Park getaway! Located just a 5-minute stroll from the Damen blue line stop, our cozy abode offers the perfect blend of convenience and comfort. Enjoy peace of mind with driveway parking. Explore the vibrant neighborhood with ease – you're just a short walk away from coffee shops, restaurants, bars, unique shopping boutiques, and so much more. Whether you're here for business or leisure, our prime location ensures you're never far from the action.

LocationFamilyCheck-in

A spacious bedroom features a king-size bed dressed in white linens, accented by a mustard yellow throw. Nightstands with lamps are positioned on either side of the bed. A decorative rug adds softness to the warm-toned wood flooring, with natural light streaming from the patio doors.

4.91 out of 5 average rating, 183 reviews

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

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A modern dining area features a dark wood table surrounded by six black chairs. A vase of colorful flowers sits at the center. A large clock hangs on the wall, and natural light filters through sheer curtains leading to a small balcony.

4.88 out of 5 average rating, 117 reviews

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.

ValueFamilyOutdoor spaces

4.87 out of 5 average rating, 132 reviews

A glass of red wine is positioned in the foreground, reflecting the soft colors of the sunset over a calm lake. The shoreline is bordered by tall grasses, framing the tranquil water and vibrant sky.

Townhouse in Westmont

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.

FamilyLocationBiking

The exterior of the United Center is illuminated at night, showcasing vibrant digital displays featuring team logos. Large glass doors welcome visitors. The venue, known for hosting concerts and sports events, is recognized by its prominent signage.

4.83 out of 5 average rating, 563 reviews

Entire House/United Center /Garage-Walk to Train

Spread out in this massive 2-story condo in the Near West Side! Enjoy multi-level privacy just steps from the United Center. Sleep comfortably in 3 bedrooms with premium mattresses (2 Kings, 1 bunk set)—all with closets & mirrors. Transportation is effortless with one included garage space and easy street parking. The Jackson bus is directly accross the street and the Blue Line is a short walk for easy downtown access in minutes.

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An open living area is seen, featuring a purple couch adorned with a decorative pillow that reads 'BEST DAY EVER.' The space includes a dining area with a clear table and modern chairs. A stylish kitchen with stainless steel appliances is visible, alongside artistic wall decor and unique mirrors reflecting the vibrant aesthetic.