Townhome vacation rentals in Near North Side

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Top-rated townhouse rentals in Near North Side

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Guest favorite

A spacious living area features a light-colored sofa and two contemporary armchairs surrounding a coffee table. A patterned area rug sits below, while a staircase with wooden steps and a modern railing leads to the upper level. Soft lighting complements the clean, neutral decor.

Townhouse in Lincoln Park

5 out of 5 average rating, 125 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

Guest favorite

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 Old Town

4.86 out of 5 average rating, 183 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!

Superhost

Townhouse in Magnificent Mile

4.83 out of 5 average rating, 218 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!

Guest favorite

The image depicts a row of charming triplex buildings characterized by brick facades and arched window details. Each unit is equipped with a garage door, and the sunlight creates a welcoming atmosphere along the quiet street.

Townhouse in North Side

4.95 out of 5 average rating, 101 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

Guest favorite

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

4.88 out of 5 average rating, 379 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/PERMIT VISITORS. Please agree per message to confirm

Top guest favorite

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

5 out of 5 average rating, 108 reviews

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.

Top guest favorite

Townhouse in Wicker Park

4.98 out of 5 average rating, 105 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.

Guest favorite

Townhouse in Near North Side

4.91 out of 5 average rating, 154 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.

Superhost

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

4.9 out of 5 average rating, 132 reviews

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!

Top guest favorite

A spacious living area features a sectional sofa with soft cushions, accompanied by a patterned area rug. A dining table with wooden chairs is visible in the background, along with a modern kitchen outlined by bright cabinetry and convenient bar seating.

Townhouse in Oak Park

4.94 out of 5 average rating, 117 reviews

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.

Top guest favorite

The entrance features a well-maintained brick façade, highlighting two sets of white stairs flanked by blooming flower pots. Large windows on either side offer views into the inviting interior. A decorative door welcomes guests, providing a glimpse of the warm atmosphere inside.

Townhouse in Ranch Triangle

4.98 out of 5 average rating, 289 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.

Guest favorite

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.

Townhouse in Lincoln Park

4.89 out of 5 average rating, 209 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.