Townhome vacation rentals in West Side

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.

4.75 out of 5 average rating, 220 reviews

Insta Worthy Prime Spot *Patio *Parking *Fireplace

Walk to almost everything Chicago has to offer- Downtown, Mag Mile, North Ave beach, zoo, and Lincoln park, restaurants, bars, boutiques. Bring family or friends to this Haute Couture Designer themed townhouse spanning over two levels on a quiet neighborhood street in historic Old Town. This amazing space has 4 bedrooms, 2.5 baths, patio, parking for 1 car, laundry, fully stocked kitchen with stainless steel appliances & granite countertops. Pets welcome! Please message me if you have questions!

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.

5 out of 5 average rating, 122 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 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.

4.83 out of 5 average rating, 216 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!

A vibrant living area features a large brown leather sectional sofa adorned with colorful pillows. A stylish white coffee table sits in the center, while an artistic mural of Chicago's skyline adds character to the backdrop. A plush area rug adds warmth to the wooden floors.

4.92 out of 5 average rating, 122 reviews

Stylish Lincoln Park Townhome Rooftop & King Suite

3-Story Townhome in Lincoln Park with Private Rooftop Step into style and comfort in the heart of Lincoln Park, where vibrant city life meets serene, tree-lined streets. Perfect for business, leisure, or family stays. Offering the perfect base to explore Chicago from one of its most sought-after neighborhoods. The Ultimate Bachelorette Getaway! Celebrate in style at this chic, spacious townhome—ideal for unforgettable bachelorette weekends. Parking pass available for added convenience.

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, 372 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, 107 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.

4.98 out of 5 average rating, 102 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.

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.

4.9 out of 5 average rating, 130 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!

Guest favorite

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

4.95 out of 5 average rating, 108 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.

4.94 out of 5 average rating, 111 reviews

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

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.

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.

4.98 out of 5 average rating, 284 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.