Townhome holiday rentals in Downtown Chicago

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, 141 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

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.

4.86 out of 5 average rating, 190 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!

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.

4.84 out of 5 average rating, 231 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!

4.96 out of 5 average rating, 113 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

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, 105 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!

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.

4.88 out of 5 average rating, 397 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

5 out of 5 average rating, 114 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.

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, 165 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.

4.89 out of 5 average rating, 140 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!

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, 107 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.

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, 303 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.