Townhouse holiday rentals in Downtown Chicago

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

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

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.

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.

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.

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.

Charming & Bright Multilevel Townhome with Parking

Plenty of space to spread out and relax! My two level townhome in the hot Old Town neighborhood makes for the perfect relaxation destination for any type of traveler. With workspaces in both bedrooms, a beautiful full-sized kitchen, free parking and laundry on-site, and the best location, you can't beat what my place has to offer. Walk to Wells St, North Ave, Lincoln Park, and the lakefront! You won't want to miss out on this unique opportunity. Book today!

Westmont 3/2 duplex Fire sunsets, Firepit, lake

Near great shopping and dining. Enjoy wonderful sunsets and quiet lake activity. Fully Stocked 20 acres lake with a neighborhood beach next door. Easy commute to downtown while enjoying the peace and quiet. Feel like you are on vacation every day. Perfect for a staycation. Cleaned to Cdc standards. This duplex is a gem in Western suburbs! Pet friendly (fee). Fire pit (bring Wood), paddleboat, kayaks. Grill and fully stocked kitchen.

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.