Mansion holiday rentals in Chicago

Find and book unique mansions on Airbnb

Top-rated mansion rentals in Chicago

Guests agree: these mansions are highly rated for location, cleanliness and more.

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Top guest favourite
The exterior of a historic building showcases large glass windows framed by green trim. Natural light streams into the space, illuminating various items displayed inside. The backdrop features a view of a nearby architectural structure, adding visual interest to the streetscape.
Apartment in Lincoln Park
4.97 out of 5 average rating, 138 reviews

Private Lincoln Park Condo with 2 Parking Spots

Built in 1895 and updated in 2025, the condo provides historic charm with modern convenience. The unit is light filled with ample space to spread out and relax. The bathroom has been fully remodeled and the kitchen is updated. The unit has a private balcony deck and a landscaped common patio. The unit includes 2 free off-street parking spots. Amenities include 60" 4K Smart TV, fiber internet, Nest Thermostat & Tuft & Needle/ Casper mattresses. Enjoy living in the heart of Lincoln Park.

Superhost
An elegant 1890 Greystone building is presented, showcasing a symmetrical façade with decorative stonework. A tiered front staircase leads to a charming entryway, flanked by well-maintained landscaping. Large windows enhance natural light, while a vibrant green shrub adds a touch of color to the exterior.
Home in West Side
4.94 out of 5 average rating, 140 reviews

Beautiful Chicago Greystone

Experience the best of Chicago from this sprawling, private 4-bedroom condo. Located just 15 minutes west of the City Center, you’re perfectly positioned to explore the culinary scene of the West Loop, the lush Garfield Park Conservatory, and the energy of the United Center Transit: Steps from multiple bus lines, 2 blocks to the Blue Line, and 1 mile to the Pink Line Amenities: On-site laundry (available upon request) Local Experts: We live in the unit below and happy to give recommendations

Guest favourite
A spacious kitchen features modern cabinetry and stainless steel appliances. An island with bar seating for eight is complemented by sleek blue chairs. Natural light fills the area from large windows, illuminating the open layout that transitions into a cozy dining space.
Home in South Loop
4.9 out of 5 average rating, 116 reviews

Large Home | Free Parking | Near Downtown

• HUGE Single Family Home | 3 Floors • Parking Garage | 2 Cars! • Chef's Kitchen | Cookware | Utensils • Basement | Two Living Rooms • 4 Bedrooms | 5 Beds | Sleeps 10 • Downtown | McCormick Place: 10min(drive) • Soldier Field | Sox Stadium: 10min(drive) • Chinatown | Pilsen Nightlife: 5min(drive) • Lakefront | Beach | Museums: 10min(drive) • Outdoor Surveillance | Noise Monitoring • Washer | Dryer | Dishwasher in unit (free) • Rideshare(Uber/Lyft) | Bikeshares(Divvy) • Working Class Neighborhood

Top guest favourite
A comfortable living area showcases a modern design with a large flat-screen TV mounted on a stone feature wall. Soft lighting highlights a cozy seating arrangement, including a plush sofa and two armchairs. A decorative coffee table sits in the center, contributing to a welcoming atmosphere.
Flat in Albany Park
4.97 out of 5 average rating, 198 reviews

NorthSide Chicago duplex 5-BD,2King size-free park

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

Guest favourite
An expansive rooftop patio is showcased, featuring woven outdoor couches with blue cushions arranged around a glass-top table. The city skyline is prominently visible, with notable buildings punctuating the clear blue sky, complemented by touches of lush greenery.
Home in Downtown Chicago
4.98 out of 5 average rating, 112 reviews

Private Downtown Retreat with Rooftop Oasis

Welcome to your exclusive retreat in the heart of the city, where urban sophistication meets unparalleled comfort. Nestled in between Magnificent Mile and Gold Coast, this luxurious Airbnb offers a haven of style and tranquility amidst the hustle and bustle. The rooftop patio offers incredible views of the city skyline, with touches of lush greenery. The spacious living areas boast oversized windows that flood the space with natural light. Each bedroom is a sanctuary where luxury meets comfort.

Guest favourite
A spacious living area features large windows allowing ample natural light. Contemporary furniture is arranged for comfort, including a leather sectional, accent chairs, and a round ottoman. The open layout leads to a modern kitchen, creating an inviting and functional space for gatherings.
Flat in Wicker Park
4.89 out of 5 average rating, 142 reviews

Luxury Designer Penthouse Loft | Sleeps 20

Designer Penthouse in the heart of Wicker Park! Sleeps up to 20 people! Enjoy your own private loft in Chicago's hip and trendy Wicker Park-one of the city's centers nightlife, restaurants and cultural scene. This 4,500 square foot penthouse sits on an entire floor features 18 foot open vaulted ceilings, authentic loft feel, 4 bedrooms/3 bathrooms, and is perfect for families, professionals visiting the city on work trips, and everything in between. The cityscape views are truly unbeatable!

Top guest favourite
Flat in Little Italy
4.99 out of 5 average rating, 329 reviews

Modern+Spacious Inn Little Italy Near W Loop W/PKG

Welcome to our super clean and thoughtfully designed 4 bedroom 2 bath first floor apartment located in the heart of Chicago’s Little Italy, in close proximity to Downtown Chicago ( two miles), West Loop, Greek Town, The Medical District and University of Illinois at Chicago Campuses. You will have no trouble reaching the hottest destinations in Chicago via foot, bike, Uber, cab, or train. Come be our guest! Please read our full listing description and house rules prior to booking.

Guest favourite
A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.
Apartment in West Town
4.96 out of 5 average rating, 209 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

Top guest favourite
A cozy living area features comfortable seating with a dark blue sofa, two armchairs, and a wooden coffee table. Natural light streams through large windows adorned with decorative frames. A small decorative tree and artwork add warmth to the space, complemented by a soft area rug.
Home in Lincoln Park
4.87 out of 5 average rating, 200 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.

Top guest favourite
The brick exterior of the three-story home features large windows that provide natural light, framed by dark accents. A set of stairs leads to the black front door, showcasing a modern design. The surrounding area includes concrete walkways and mature trees.
Home in Wrigleyville
4.99 out of 5 average rating, 107 reviews

Wrigleyville Single Family

Private single family home one block from Wrigley Field! Enjoy three levels of living all to yourself. Totally gut renovated home with a chef's kitchen, central heat/air, washer/dryer, and three full bathrooms. Three bedrooms on the second level with a full basement/ bedroom with its own bathroom. Large back deck off the kitchen with a gated parking pad for one large vehicle included. Have an amazing time in the very heart of Wrigleyville.

Guest favourite
A charming Victorian home is showcased, featuring a front porch with wide steps leading to a door framed by lush greenery. The exterior is painted in a crisp white, complemented by dark accents on the windows. A manicured lawn adds to the inviting landscape.
Home in Oak Park
4.96 out of 5 average rating, 132 reviews

Oak Park Victorian by FLW Studio

Discover historic charm in our updated 4-bedroom Victorian home in the iconic Frank Lloyd Wright district. Comfortably sleeps 8. Features a fully equipped kitchen, dedicated workspace, and modern amenities. Perfectly located for exploring local gems on foot or a quick 15-min drive to downtown Chicago. Enjoy private parking and easy access to public transit. Ideal for families and groups seeking a stylish, central retreat.

Top guest favourite
A cozy living area showcases a brown leather sofa adorned with decorative cushions. A round glass coffee table rests on a patterned rug, complementing the hardwood flooring. Framed artwork decorates the wall, while natural light enters through nearby windows.
Home in Logan Square
4.98 out of 5 average rating, 132 reviews

The Hamlin | Logan Square Home 4BR/2BA w Parking!

✨ Your Chicago Stay, Elevated. 🏡 Welcome to The Hamlin House in Logan Square This design-forward home features 4 bedrooms 🛏️, 2 full bathrooms 🚿, and included two-car garage parking 🚗🚗 — perfect for family trips or group getaways. ⸻ 🌿 Logan Square You’re in Logan Square, known for its amazing food 🍽️, local art 🎨, historic boulevards 🏛️, and easy access to downtown 🌆 — all without downtown hotel pricing.

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