Townhouse holiday rentals in Near North Side

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.

4.85 out of 5 average rating, 273 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.)

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.

4.99 out of 5 average rating, 129 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

4.95 out of 5 average rating, 105 reviews

Townhouse in North Side

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

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.

4.97 out of 5 average rating, 101 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!

4.88 out of 5 average rating, 385 reviews

A wall-mounted shelf displays a selection of games and activities. Notable items include a colorful game box labeled 'Charades', along with stacks of miscellaneous game pieces. Above the shelf, the word 'PLAY' is spelled out using wooden blocks, adding a playful touch to the space.

Townhouse in West Town

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/PERMIT VISITORS. Please agree per message to confirm

5 out of 5 average rating, 111 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

Fully Furnished 2-story, 2 bedroom attached Duplex with a King bed in the Primary bedroom and a pair of Twin beds in the 2nd bedroom. Couch on main floor is also a sofa bed that sleeps two if needed. Main floor is wide open floor plan. This space has been set up specifically for short-term rentals of 1-2 weeks or months and has previously been used by Guests looking for homes in the Evanston area or having construction done. We cater to Families visiting Northwestern University.

Townhouse in Near North Side

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, 158 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.

4.9 out of 5 average rating, 134 reviews

The living room features a light-colored sofa and two burgundy armchairs arranged around a square coffee table. Large windows allow natural light to fill the space, with a decorative rug adding texture to the floor. A television is mounted on the wall, complementing the modern decor.

Townhouse in River West

Upscale 4-Bedroom Townhouse w/Garage - LOCATION

In the heart of Chicago's River West, this professionally-designed 4BR/2.5BA townhouse is right in the middle of it all! You can easily walk to West Loop, River North, and the Loop - all home to some of the best restaurants and attractions Chicago has to offer. Your travel to/from the city will be extra convenient with access to a private one-car garage spot and street parking. With 4 bedrooms and 5 beds across 3 floors, your group will have plenty of space to enjoy Chicago!

4.94 out of 5 average rating, 121 reviews

Townhouse in Oak Park

Downtown Oak Park - Luxury 3 bed 3.5 bath Townhome

Entire townhome located in charming downtown Oak Park. Luxury accommodations. Free Parking. Dog friendly. Highly-walkable area. Attached two-car garage. Chicago's El and Metra train stops a short 2-block walk. Both trains bring you to the heart of downtown with the El extending into many Chicago neighborhoods. Shopping, restaurants, Target, Trader Joe's and Frank Lloyd Wright homes within walking distance. TVs logged into Hulu, Disney +, ESPN, Netflix and HBO Max.

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, 104 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.

Townhouse in Ranch Triangle

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, 295 reviews

Beautiful Lincoln Park/ De Paul Complimentary Parking Permit

This generously sized, quiet apartment, located in the highly sought-after Lincoln Park neighborhood, offers convenient access to acclaimed restaurants and boutiques, all within a five-minute walk. Its private entrance and proximity—less than four blocks—to both the Red and Brown Line "L" stations ensure effortless access to Chicago's attractions, most within a two- to five-stop train ride. Zoned parking permits are provided.

A spacious living room features a comfortable white sectional couch positioned on a light area rug. A sleek glass coffee table is centered in front of the couch. A modern media console with wall-mounted shelves displays decorative items, while natural light streams through a large window with sheer coverings.

4.88 out of 5 average rating, 214 reviews

Cheerful 3 story townhouse Old Town/LP

Discover a luxurious three-story townhouse, ideally located for exploring Chicago's Lincoln Park Zoo, Lake Michigan, Magnificent Mile, Old Town, and Lincoln Park's vibrant dining and shopping. Enjoy a complimentary designated parking spot. Please note: due to a host's medical condition, we cannot accommodate service animals that are cats or dogs. A fee applies for more than two guests.

Popular amenities for Near North Side townhouses

Kitchen

Wi-Fi

Free parking on premises

Air conditioning

Family-Friendly townhouses

5 out of 5 average rating, 7 reviews

The open living area features a striking mural inspired by Van Gogh, complemented by blue sofas arranged around a round coffee table. Natural light enhances the warm wooden flooring, while a staircase leads to the upper level. Ceiling fans are visible, promoting airflow.

Townhouse in River West

A Starry, Central, Artsy, Stylish Home by L Stop

A modern dining area features a wooden table surrounded by blue chairs, enhancing the vibrant atmosphere. A large abstract artwork adds color to the wall, while a spiral staircase leads to the upper levels of the townhome.

4.82 out of 5 average rating, 44 reviews

3-Story,Free Parking,No Pet Fee,Private Patio,W/D

A vibrant mural depicting a cosmic landscape with stars and colorful mountains is displayed on the wall above a cozy orange sofa. The sofa is adorned with plush blue pillows, creating an inviting space for relaxation and conversation.

Townhouse in West Town

4.76 out of 5 average rating, 83 reviews

Charming & Comfy Gem ~ 10 Mins to Downtown ~Patio!

A spacious bedroom is presented with a wooden bed framed by intricately designed posts. A mirror and dresser complement the room, while natural light filters through sheer curtains. A standing lamp adds additional illumination, creating a bright and airy ambiance.

4.83 out of 5 average rating, 6 reviews

Shared home / Parking / McCormick Place Center - L

A charming duplex is set behind a lush green landscape, featuring a welcoming front porch with steps leading to a blue front door. Tall windows allow natural light to fill the home, while surrounding trees and shrubs contribute to a peaceful atmosphere.

Townhouse in Oak Park

4.79 out of 5 average rating, 33 reviews

4 bed/1.5 bath townhouse in FLW Historic District!

5 out of 5 average rating, 28 reviews

A decorative tray is displayed on a neutral-toned couch, featuring a white vase filled with faux white foliage and a black candelabra holding two tall white candles. A wall art piece and a green plant can be seen in the background.

Townhouse in Orland Park

Luxurious townhome 30 days lease open for 2 weeks

Townhouse in Des Plaines

4.53 out of 5 average rating, 234 reviews

Chicago ORD Family Retreat – 2BR/2BA • Sleeps 8

Townhouse in South Shore

5 out of 5 average rating, 4 reviews

3-Level Townhome Near Soldier Field and Downtown

Townhouse rentals with a washing machine and dryer

Townhouse in Little Village

A modern bedroom features a spacious bed with a patterned black and white comforter. Two bedside lamps illuminate the space. Bright natural light filters through sheer white curtains, and a large artwork depicting a street scene with a red bicycle enhances the wall above the bed.

4.94 out of 5 average rating, 51 reviews

Urban Oasis in Heart of Chicago

4.96 out of 5 average rating, 74 reviews

A modern living area features a sectional sofa and a round coffee table, surrounded by indoor plants. A large wall-mounted flat panel television is visible, and natural light floods through the large windows, which lead to an outdoor balcony. A textured rug adds warmth to the space.

Townhouse in River West

Beautiful Spacious RiverWest Townhome 4-Bed/4-Bath

4.75 out of 5 average rating, 81 reviews

The facade of the historic townhome is showcased, featuring a prominent bay window and decorative architectural details. A vibrant red door serves as a focal point, complemented by large windows that allow natural light to fill the interior. Surrounding greenery adds to the inviting aesthetic.

Townhouse in Lake View

Historic Alta Vista Terrace District

4.87 out of 5 average rating, 131 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

4.75 out of 5 average rating, 224 reviews

A comfortable living area features a dark upholstered sofa with decorative pillows, complemented by a round glass coffee table atop a patterned area rug. A dining set is positioned in the background, and wooden cabinets are visible in the kitchen area.

Townhouse in Old Town

Insta Worthy Prime Spot *Patio *Parking *Fireplace

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.

4.87 out of 5 average rating, 102 reviews

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

4.93 out of 5 average rating, 68 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 Woodlawn

*Hyde Park *2 Masters *2 Living Rooms *Courtyard

4.93 out of 5 average rating, 42 reviews

A well-lit bedroom features a spacious bed with crisp white linens and decorative pillows. A wooden dresser stands alongside a woven basket, and a geometric area rug is placed on the floor. Warm light from a bedside lamp enhances the neutral color scheme.

Townhouse in Lake View

Ideal Lakeview location! Walk to Wrigley, DePaul

Townhouses with a patio

4.88 out of 5 average rating, 24 reviews

The exterior of a modern row house is displayed, featuring textured stone walls and a garage door. Two large windows with railings are positioned above the entrance. Subtle outdoor lighting illuminates the front, complemented by a small decorative wreath on the door and seasonal foliage on the ground.

Townhouse in West Town

Chicago West Town Row House

4.98 out of 5 average rating, 43 reviews

Townhouse in Oak Park

A Pleasant Stay in Oak Park

Townhouse in Lincoln Square

A multi-unit building is shown surrounded by well-maintained green lawns and hedges. Outdoor seating areas with umbrellas are visible, providing a relaxed space for guests to enjoy the fresh air. The clear blue sky highlights the inviting exterior and garden spaces.

5 out of 5 average rating, 31 reviews

Northside Famlynest Lincoln Sq 4BR/1.5BA/2P

The modern kitchen features deep wooden cabinetry and a granite countertop, complemented by stainless steel appliances. A dining table with six chairs is positioned beside large windows, offering a view of the outdoors. The space is illuminated by both natural and artificial light.

4.98 out of 5 average rating, 52 reviews

Chinatown 3 bedroom with Parking - near McCormick

4.96 out of 5 average rating, 115 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 Plaines

Upscale 3 bed 1.5 bath near Chicago O'Hare Airport

4.9 out of 5 average rating, 50 reviews

A living room area features two dark leather sofas arranged around a glass coffee table set on a patterned rug. A desk with a chair is visible, illuminated by blue overhead lights, while sheer curtains frame a window.

Townhouse in Evanston

Entire Cozy Townhouse

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.

4.69 out of 5 average rating, 130 reviews

Charming & Bright Multilevel Townhome with Parking