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Mansion vacation rentals in Chicago

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Top-rated mansion rentals in Chicago

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Top guest favorite

Apartment in Albany Park

4.97 out of 5 average rating, 156 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!

Condo in West Town

4.94 out of 5 average rating, 143 reviews

711 The Penthouse

Luxurious upscale Duplex Penthouse-River West neighborhood in downtown Chicago! Newly rehabbed and updated interior design that is mind blowing. Over 5600 sq ft. Features 5 bedrooms, 2.5 baths, 3 largeTVs with sonos sound system, game room!!. Near CTA Blue Line, close to the best dining and attractions of Chicago! Two large living areas perfect for hosting small events, bachelor(ette) parties, bridal or baby showers, work/travel, and family reunions. Rooftop with beautiful view of the skyline!

A bright kitchen area is visible, featuring white cabinetry and a spacious island with seating for two. Natural light fills the space through large windows, and a small potted plant adds a touch of greenery. Stylish pendant lights hang above the island.

Home in Glen Ellyn

4.91 out of 5 average rating, 155 reviews

Home in Glen Ellyn

Beautiful 5 bedroom, 2.5 bath home in Glen Ellyn, fully furnished with everything you may need for a wonderful stay! Located in the peaceful suburbs of Glen Ellyn, the area is perfect for families or friends who would like a comfortable getaway. Located 40 minutes from downtown Chicago and Midway airport and 30 minutes from O'Hare airport. Located nearby major highways and shopping centers. Large, private and completely enclosed backyard perfect for kids to play in or a relaxed evening of BBQ!

A grand staircase with ornate wooden balusters ascends from a spacious foyer. Natural light floods the room through large windows, illuminating the polished hardwood floors. A comfortable seating area is visible to the right, complemented by light-colored furniture and a circular mirror on the wall.

Townhouse in Magnificent Mile

4.83 out of 5 average rating, 207 reviews

Historic lux Townhouse on Chicago's Gold Coast

Welcome to our stunning Townhouse located in the luxurious Gold Coast of Chicago. Perhaps the BEST location in Chicago! Located on one of the desirable & famous streets in Chicago, this property is a 5 min walk from the Gold Coast beach where you will see Lake Michigan in all of its glory. Not to mention the proximity of this property to the subway and within walking distance of Magnificent Mile. It is the perfect place to stay for the adventurous and also those who fancy a beach in the City!

A spacious guest room features plush bedding with patterned covers atop two king beds. A sleek coffee table is positioned in front of a comfortable seating area, accompanied by a modern TV mounted on the wall. Soft lighting enhances the welcoming ambiance of the space.

Home in Bensenville

4.81 out of 5 average rating, 102 reviews

Skyway w/ Shuffleboard

Welcome to our spacious split-level home– an inviting retreat perfect for families, groups of friends, and business travelers. This comfortable haven combines the convenience of a prime location with all the amenities you need for a relaxing stay. Have some fun with family and friends by laying a shuffleboard tournament. Enjoy plenty of room to spread out, fun entertainment, beautiful backyard, plenty of parking, 5 King beds and easy access to Chicago’s attractions via Metra or expressway.

A contemporary art piece is displayed on a wall, featuring soft colors with subtle blue streaks. On a polished black table, two decorative vases in contrasting styles are positioned, along with a textured coral sculpture, creating a stylish accent in the space.

Apartment in Lake View

4.84 out of 5 average rating, 307 reviews

Comfy/Elegant Home by Wrigley, Garage Spot & Yard

This chiq duplex home near Wrigley Field is a hidden gem. It features 6 beds, a garage parking spot; and a fenced yard; with 5 bedrooms, 3 baths, a spacious living & dining area and fast gigabit internet. In an unbeatable location close to many popular attractions, this home is the perfect base for your Chicago adventures. 6 min drive to: -Wrigleville -Andersonville & Boystown -Montrose Beach -Uptown, Green Mill, Riviera / Aragon Theaters 15-20 min drive: Cloudgate, Downtown, Loop!

Top guest favorite

The exterior of a multi-unit apartment building is surrounded by vibrant green trees, providing shade and a welcoming atmosphere. Large windows reflect natural light, and a front staircase leads to the entrance. The building features a combination of brick and light-colored stone elements.

Apartment in Little Italy

4.99 out of 5 average rating, 274 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.

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.

Condo in West Town

4.98 out of 5 average rating, 166 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 favorite

Apartment in Oak Park

4.98 out of 5 average rating, 116 reviews

The Chicago Game Room (Oak Park, IL)

There is no other rental like this in the Chicago area! Located in the first suburb west of Chicago, this 4-bedroom, two-level private apartment is brand new and ready for your group to enjoy. It features an amazing game room/living room with cathedral ceilings, skylights, gas fireplace, bar seating, pool table, shuffleboard/bowling table, dart board, four bedrooms + sleeper sofa, full kitchen, spa-like bathrooms, in-unit washer/dryer, and private deck. GUESTS = 8 MAX

A welcoming entryway features a polished wooden door and a decorative stained glass panel framed on the wall. The floor showcases intricate marble tiles, combining shades of dark and light, while a wooden bench is positioned against the wall for added convenience.

Apartment in Hyde Park

4.94 out of 5 average rating, 525 reviews

Hyde Park 5 Bed/3 Full Bath Condo- Travelers Only!

This will likely be the largest condo you have ever seen. This condo is 5 mins from the University of Chicago and the University of Chicago hospital. You will be a quick 10-15 min uber ride from downtown and 5 mins from beautiful Lake Michigan. We are currently only booking out of town travelers. We are not doing parties or events. I live in the building so if you are trying to have a party I will have it shut down and you will be asked to leave within an hour.

Home in Lincoln Park

4.85 out of 5 average rating, 173 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.

An open dining area is furnished with a large wooden table set for multiple guests. Soft, natural light fills the space, reflecting off a decorative area rug. A cozy armchair and two accent tables complement the warm and inviting ambiance.

Home in Avondale

4.84 out of 5 average rating, 121 reviews

The Logandale: HUGE Mid-Century Home, sleeps 15

Welcome to The Logandale! This 4 bed/3 bath mid-century modern home is ideal for families, professionals, and groups. Enjoy an open floor plan, private patio, game room, and bedrooms with memory foam mattresses. The fully-equipped kitchen, Smart TVs with Netflix, and a backyard fire pit ensure a comfortable stay. Located in the trendy Avondale/Logan Square, you're close to public transport, eateries, and attractions. Experience Chicago's best with us! 🌃🛏️🎮🔥

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Popular amenities for Chicago mansion rentals

Free parking on premises

Air conditioning

Mansion rentals with a pool

A spacious living room is featured with a cream-colored sectional couch facing a mounted flat-screen TV. Natural light pours in through large windows adorned with blinds. A stone accent wall adds texture, complemented by two decorative pieces and a ceiling fan.

Home in Munster

5 out of 5 average rating, 11 reviews

Munster hide away

A sunny backyard features a round in-ground pool surrounded by lush green grass and vibrant flower pots. The house showcases a two-story design with a balcony and large windows, providing views of the serene outdoor space and nearby landscaping.

Home in Des Plaines

5 out of 5 average rating, 4 reviews

Rosemont 4BD2BA house with Pool

A spacious basement game area features a classic pool table with a vibrant green felt surface, complemented by cues and an arranged set of colored balls. Nearby, a seating area with leather couches and an arcade machine is visible along the wooden-paneled wall.

Home in Bloomingdale

4.92 out of 5 average rating, 52 reviews

Now Open: Heated Pool with Entire House

An indoor heated pool is surrounded by large windows and glass doors, allowing natural light to fill the space. The vaulted ceiling features skylights and ceiling fans. A blue bench lines one side of the pool, creating a relaxed environment with views of the outdoor area.

New place to stay

Luxe heated indoor pool/hot tub

A modern living room features a vibrant orange sofa with two decorative pillows, accompanied by a green armchair. A glass coffee table holds a wooden tray and a decorative item. Large windows allow natural light to fill the space, revealing an urban view.

Apartment in The Loop

4.5 out of 5 average rating, 4 reviews

Two Units: Seamless Stay, Downtown Convenience

An outdoor area features a spacious swimming pool surrounded by a wooden deck, offering ample space for relaxation. Lush trees provide privacy, with the home visible in the background. The deck shows a gentle slope leading toward the water, facilitating easy access to the pool.

Cabin in New Lenox

4.59 out of 5 average rating, 69 reviews

Your favorite vacation spot

An aerial view captures a landscaped amenity yard featuring an indoor hot tub house and multiple lounge seating areas. A mix of patio furniture in shades of blue is arranged over green grass. The outdoor space is surrounded by trees and includes access to the rear deck.

Apartment in Logan Square

4.93 out of 5 average rating, 14 reviews

2-level PH w/ 2 Luxe Suites Combined; Spa Access

A spacious living area features a large sectional sofa in black, complemented by two vibrant blue armchairs. Light wood flooring reflects the soft illumination from recessed lighting. Large windows provide a view of the outdoors, while a sleek black television sits above a stylish fireplace.

Home in Logan Square

4.63 out of 5 average rating, 8 reviews

Stunning Home in Prime Chicago with Private Pool

Luxury mansion rentals

A well-furnished living room is displayed with a neutral color palette. Seating includes beige chairs and a cream-colored sofa around a coffee table. Natural light filters through plantation shutters on large windows, and decorative wall art and a textured area rug add interest to the space.

Townhouse in West Town

4.95 out of 5 average rating, 224 reviews

Luxury River West Townhome with Garage

A modern living area is visible, featuring light-colored sofas arranged around a wooden coffee table. A large flat-screen TV is mounted on a wall. The space includes a dining area with a table and chairs, while neutral walls complement white cabinetry in the kitchen.

Home in Avondale

4.89 out of 5 average rating, 248 reviews

Spacious 6BR in Logan Square + Garage! Sleeps 16

Condo in Pilsen Historic District

4.94 out of 5 average rating, 129 reviews

The Urban Oasis | Outdoor Lounge • Sleeps 10+

The entrance of Wrigley Field is depicted, showcasing the iconic red marquee sign indicating the home of the Chicago Cubs. Flags flutter gracefully above crowds of fans, with a vibrant atmosphere highlighted by the greenery and historic architecture surrounding the entrance.

Home in Lake View

4.89 out of 5 average rating, 175 reviews

Lake View | Wrigley Designer House w/Patio

An inviting entryway features two black doors adorned with detailed glass panes. A stylish staircase with wooden banisters leads upward. Artwork and photographs are displayed on the walls, while a small green plant adds a touch of life to the corner.

Condo in Lincoln Park

4.96 out of 5 average rating, 108 reviews

Large Remodeled Home in Lincoln Park, Sleeps 12!

Top guest favorite

A welcoming entrance is highlighted by two wooden doors with glass panels, set against a warm wooden porch. Potted greenery adds a touch of nature, while a doormat with a friendly greeting enhances the inviting atmosphere.

Home in Portage Park

4.97 out of 5 average rating, 117 reviews

Ultra Modern, 2800 SQ Ft, Outdoor Gazebo Sleeps 14

A spacious sectional sofa in a soft gray fabric is positioned in a well-lit basement area. Natural light enters through a small window, illuminating the inviting layout. The carpeted floor complements the relaxed setting, ideal for family gatherings or leisure activities.

Home in Justice

4.93 out of 5 average rating, 227 reviews

3 Kng, 1 Qn, 1 Full, 3AirBd|Basktbll Crt|FreePrkin

Home in Irving Park

4.87 out of 5 average rating, 125 reviews

Stunning 6 BR Home * Chicago * Centrally Located

Pet-friendly mansion rentals

A living room features a cozy seating arrangement including a spacious sofa and armchairs, accompanied by a round coffee table. A fireplace is set beneath a wall-mounted television. Natural light enters through floor-length curtains, while decorative artwork adorns the walls.

Home in Chicago

4.93 out of 5 average rating, 30 reviews

Bronzeville Home! Downtown + McCormick + U of C

A spacious living room is highlighted by a sectional sofa adorned with orange and white cushions. A round wooden coffee table complements an accent chair, while a tall plant adds a touch of greenery. Natural light filters through the sheer curtains, enhancing the neutral decor.

Home in Burbank

4.96 out of 5 average rating, 70 reviews

Luxurious House 25 min for downtown

Top guest favorite

A charming gray house with a well-maintained exterior is framed by a black fence. Steps lead up to a covered porch adorned with flower boxes, while a grassy area is visible beside the home, contributing to the inviting curb appeal.

Home in Avondale

5 out of 5 average rating, 17 reviews

Alluring Avondale Abode

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.

Condo in Lincoln Park

4.96 out of 5 average rating, 94 reviews

Private Lincoln Park Condo with 2 Parking Spots

A bright and inviting living room features a comfortable sofa adorned with patterned cushions. A soft throw is draped over an ottoman. Natural light filters through a large window, and a 'WELCOME' sign is displayed on the wall, enhancing the space's approachable atmosphere.

Home in Elmhurst

4.93 out of 5 average rating, 165 reviews

The Ultimate Escape|Unpack|Relax|Enjoy!Sleeps10-14

4.95 out of 5 average rating, 57 reviews

Culinary DREAM - Pizza Oven/BBQ/Smoker

An inviting dining area features a large wooden table surrounded by white chairs. A circular mirror adorns the wall, while natural light fills the space, highlighting large plants positioned throughout. A small side table displays a vase with sunflowers, adding a touch of greenery.

Apartment in West Town

4.88 out of 5 average rating, 110 reviews

Comfy&Spacious | Close 2 Downtown | Parking +Patio

A row of charming brick homes showcases American flags and seasonal decorations. A group of visitors gathers on the sidewalk, engaged in a guided tour. Lush greenery and colorful flowers surround the entryways, enhancing the neighborhood's inviting atmosphere.

Townhouse in Pullman

4.86 out of 5 average rating, 76 reviews

Large Executive Row house in Historic Pullman

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