Townhouse holiday rentals in Chicago

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, 287 reviews

Fulton Market Townhome, 4 Levels & 4 Bedrooms

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.

LocationFamilyTV

4.93 out of 5 average rating, 152 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

FamilyLocationOutdoor spaces

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.

4.98 out of 5 average rating, 335 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.

FamilyLocationBreakfast

Townhouse in Logan Square

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.

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.)

LocationFamilySleep quality

4.86 out of 5 average rating, 308 reviews

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, 166 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

FamilyLocationSleep quality

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.

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!

ValueFamilyNearby

4.95 out of 5 average rating, 127 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

LocationFamilyAir conditioning

Townhouse in Belmont Cragin

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.

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!

FamilyLocationCheckout

4.98 out of 5 average rating, 125 reviews

4.97 out of 5 average rating, 155 reviews

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

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.

FamilyValueCheck-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, 184 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.

ValueFamilyAir conditioning

4.95 out of 5 average rating, 138 reviews

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

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

ValueLocationGetting around

4.88 out of 5 average rating, 118 reviews

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

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.

LocationValueIndoor spaces

Popular amenities for Chicago townhouses

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-Friendly townhouses

5.0 out of 5 average rating, 124 reviews

An open floor plan living area features a spacious couch paired with a dark coffee table. A soft area rug complements the hardwood flooring. The dining area is visible, showcasing a table for six. Large windows provide natural light to the inviting space.

Townhouse in Evanston

The NICEST place in Evanston for Families 1500Main

FamilyValueGetting around

4.95 out of 5 average rating, 308 reviews

The living room features a comfortable seating arrangement, including a dark couch and a lounge chair. Large windows allow natural light to fill the space, while a television is positioned on a media console. A ceiling fan adds to the room's functionality.

Townhouse in Edgewater

The Nancy’s gorgeous , Spacious Urban Getaway

FamilyLocationBathroom

4.88 out of 5 average rating, 130 reviews

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.

Townhouse in West Town

Wicker Park Crash Pad + 7 Beds

ValueFamilyNearby

4.93 out of 5 average rating, 265 reviews

A spacious living area is furnished with a mix of comfortable seating, including an elegant chair and a pair of armchairs. A central wooden coffee table is surrounded by decorative candles. Natural light streams through large shuttered windows, illuminating the warm color scheme and wooden flooring.

Townhouse in West Town

Luxury River West Townhome with Garage

LocationValueTV

Townhouse in Hoffman Estates

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.

a SIMPLE place

LocationFamilyNearby

4.9 out of 5 average rating, 393 reviews

4.96 out of 5 average rating, 180 reviews

The living and dining area presents an open-concept design, featuring a large sectional sofa with decorative pillows, a glass coffee table, and a television. A dining table with ample seating is positioned near the large window, allowing natural light to illuminate the space.

Townhouse in Uptown

Ravenswood 4BR Rowhouse + Free Parking Included

FamilyLocationParks

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

LocationValueCheck-in

4.97 out of 5 average rating, 123 reviews

A bright living area features a large sectional sofa and a coffee table positioned on a light rug. Natural light fills the space through large glass doors that lead to an outdoor view. A ceiling fan is installed overhead, and decorative plants add a touch of nature.

Townhouse in Naperville

Newly Renovated Home Near Naperville Downtown

ValueLocationLong stay

Townhouse rentals with a washing machine and dryer

4.87 out of 5 average rating, 115 reviews

A spacious living area features a large sectional sofa and a modern coffee table at its center. Sunlight streams through wide windows, illuminating the light-colored walls and floor. A subtle piece of artwork is displayed on the wall, enhancing the relaxing ambiance.

Townhouse in South Loop

Sanitized Home, 4BR/3BA, Free Parking available

FamilyValueBathroom

4.9 out of 5 average rating, 101 reviews

The open living area features a modern staircase with wooden steps and a metal railing. A light-colored sofa adorned with decorative cushions faces a dining space with a large table and stylish light fixtures. Exposed brick walls add warmth to the contemporary decor.

Townhouse in South Side

Artistic Stay near Hyde Park: 2 Living, Courtyard

FamilyLocationIndoor spaces

4.81 out of 5 average rating, 36 reviews

Townhouse in Lisle

Luxury New Build 3BR Townhome

LocationFamilyCleanliness

An inviting entrance features a covered porch with hanging flower baskets. A small outdoor seating area with two blue chairs and a matching table is situated beside a well-maintained garden. The garage door offers additional convenience and security for guests arriving by car.

4.99 out of 5 average rating, 76 reviews

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

ValueLocationWi-Fi

Townhouse in West Rogers Park

Cheerful 3-bedroom townhome in west rogers park!!

FamilyValueHeating

4.88 out of 5 average rating, 98 reviews

4.68 out of 5 average rating, 47 reviews

Modern Luxurious Home Near Beach, Park

ValueFamilyNearby

5.0 out of 5 average rating, 6 reviews

Townhouse in West Side

Stylish Condo Near Medical District & UIC campus

LocationFamilyAmenities

The living room features a plush sectional sofa and two mustard-colored chairs, arranged around a warm fireplace. Large windows provide natural light and a view of greenery. A flat-screen TV is mounted above the fireplace, enhancing the cozy atmosphere of the space.

4.84 out of 5 average rating, 111 reviews

West Loop 3BD/2BA TH | 2 Jacuzzis | Garage Parking

LocationValueHospitality

Townhouses with a patio

The living area offers a bright and inviting space with large windows allowing natural light to flood in. A comfortable sofa is positioned alongside two armchairs, with a coffee table set in the center. A fireplace is located beneath a wall-mounted television.

4.97 out of 5 average rating, 66 reviews

Luxurious Home in Chicago Fulton Market Downtown

FamilyValueBathroom

4.91 out of 5 average rating, 45 reviews

Spacious 3-Bed West Loop Townhouse, 1 Car Garage

FamilyLocationHospitality

4.86 out of 5 average rating, 36 reviews

Townhouse in West Town

Chicago West Town Row House

FamilyLocationDecor

Townhouse in Wrigleyville

An entryway leads into a bright living area featuring a white sofa and a wooden coffee table. A light fixture with multiple bulbs adds a modern touch. The open kitchen with white cabinetry is visible in the background, contributing to the spacious feel.

Chicago Wrigleyville Townhouse

ValueLocationCheck-in

4.93 out of 5 average rating, 61 reviews

4.96 out of 5 average rating, 81 reviews

Townhouse in Oak Park

A Pleasant Stay in Oak Park

LocationValueBathroom

A living room features a comfortable grey sofa and stylish orange chair, with a white coffee table centered on an ornate area rug. A television sits on a wooden media console, and an elegant fireplace is located on one side, adding a touch of warmth.

4.71 out of 5 average rating, 167 reviews

Charming & Bright Multilevel Townhome with Parking

ValueFamilyLong stay

4.85 out of 5 average rating, 13 reviews

Townhouse in Des Plains

Plaines Cozy Corner

LocationValueComfort