Townhouse holiday rentals in West Side

Find and book unique townhouses on Airbnb

Top-rated townhouse rentals in West Side

Guests agree: These townhouse rentals are highly rated for location, cleanliness and more.

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Top Guest favourite

A spacious living area showcases a comfortable L-shaped leather sofa adorned with decorative pillows. A glass coffee table is positioned on an elegant area rug, while framed art pieces decorate the walls. A floor lamp provides soft lighting next to a small side table with a decorative plant.

Townhouse in Lincoln Park

4.98 out of 5 average rating, 332 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

Located in the heart of Lincoln Park's Armitage/Halsted shopping district, one of Chicago's most desirable and walkable neighborhoods, steps from boutiques, cafés and public transit are all within a short walk. This is an urban, pedestrian friendly neighborhood where many visitors choose to explore on foot. Complimentary daily parking permits included. Please note that the apartment does not have an in-unit washer/dryer. For longer stays, laundry credit is provided for wash and fold service.

LocationValueSleep quality

Guest favourite

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.

Townhouse in Logan Square

4.86 out of 5 average rating, 305 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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Guest favourite

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.

Townhouse in Lincoln Park

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

FamilyLocationQuiet

Top Guest favourite

The living room features a high ceiling and a stone fireplace, with large windows allowing natural light to fill the space. Two brown leather sofas and a wooden coffee table create a cozy sitting area. The outdoor space is accessible through double doors.

Townhouse in Downtown Chicago

4.87 out of 5 average rating, 205 reviews

Downtown Elegance ✨ Private Yard Parking

Most incredibly located, sun-filled home with designer kitchen, marble baths, and open-concept living areas—perfect for weekend friend getaways and weekday family or work trips. Walkable to so much of what Chicago has to offer, this spacious townhouse is located on a quiet, safe neighborhood street in historic Old Town. 4 bedrooms, 4 baths, 2 outdoor spaces, fully stocked kitchen, 1-car parking, and laundry. Pets are welcome! What else could you possibly need? Message me if you have questions!

FamilyValueCleanliness

Top Guest favourite

Townhouse in Lincoln Park

4.96 out of 5 average rating, 126 reviews

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

ValueFamilyKitchen

Top Guest favourite

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.

Townhouse in Wicker Park

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.

LocationValueKitchen

Guest favourite

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.

Townhouse in Downtown Chicago

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.

ValueLocationHeating

Guest favourite

A sleek wall-mounted television is set above a modern electric fireplace, framed by a stylish metallic trim. The stone feature wall provides a textured backdrop, while warm wood flooring complements the contemporary design.

Townhouse in Des Plains

4.95 out of 5 average rating, 135 reviews

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

ValueFamilyBackyard

Guest favourite

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.

Townhouse in South Loop

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.

FamilyLocationDecor

Guest favourite

A cozy living area features a black leather sofa paired with decorative pillows. A glass coffee table sits atop a patterned rug, complemented by a lamp and a small plant. The staircase leads to an upper level, with a wall map artwork enhancing the space.

Townhouse in Hoffman Estates

4.9 out of 5 average rating, 391 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.

ValueLocationNearby

Top Guest favourite

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

4.87 out of 5 average rating, 132 reviews

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.

FamilyLocationAmenities

Guest favourite

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.

Townhouse in West Side

4.83 out of 5 average rating, 564 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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