Mansion vacation rentals in Chicago

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Top-rated mansion rentals in Chicago

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Guest favorite

Home in Wicker Park

4.98 out of 5 average rating, 153 reviews

Spacious Five Bedroom Home in Trendy Chicago Neighborhood

Unwind on the private rooftop deck, soak in the luxurious jacuzzi tub or take a relaxing steam shower after you host a dinner party in your own spacious dining room. Then watch a movie in the entertainment center with popcorn machine and 75 inch TV. Bedrooms are as follows: Master - king 2nd - twin and crib 3rd- queen 4th - twin over full bunk 5th - king and twin over twin bunk We also have a large, U shaped, 40 inch deep Cloud sectional from RH that can sleep 2-3 and 2 air mattresses. Stunning newly renovated home in a fantastic Wicker Park Location! Wicker Park is the Brooklyn of Chicago with tons of unique shops, restaurants full of character and innovative bars. The entire home is yours, giving you rarely found complete privacy in the middle of the city for you, your family, friends and colleagues to enjoy! Expertly designed with gourmet kitchen and multiple living rooms, your party will have plenty of room to spread out during your stay in the Windy City. Utilizing the finest materials & craftsmanship available, some of the premium features include: hardwood flooring on entire 1st and 2nd levels, 10' ceilings, beautiful moldings, sensational gourmet kitchen with large center island, premium stainless appliances and quartz counters, extra-large bedrooms including luxurious master suite with lavish marble baths, steam shower and expansive walk-in closet. Five full bedrooms and 4 bathrooms. The master bedroom has a King bed and very large ensuite bathroom. Bedroom 2 has a twin bed and a crib (upon request), bedroom 3 has a queen bed and a daybed. Bedrooms 2 and 3 share a hall bath. Bedroom 4 has bunk beds and bedroom 5 has a king bed and a daybed. Bedrooms 4 and 5 share a bathroom. The basement has a large entertainment area with a wine fridge, popcorn machine and 75 inch TV. **For those with infants and toddlers, in addition to a crib, we also have a SNOO bassinet and a Bugaboo cameleon stroller for your use. **If you would like to use any of these, please specify in your booking so that we can have them out and available to you. Otherwise, we keep them out of the way for guests who are not needing them. If you need parking please let me know in advance ** We have keyless entry for super easy check in. I am always available by phone, texting is best, but we want you to have the most convenience possible. That’s why we have keyless entry for seamless check in. No hassle for late arrivals, etc. Simply type in the code provided after confirmation and you’re all set! The neighborhood is the most buzzed about in Chicago, with trendy restaurants, shops, and bars within an easy walk, not to mention the beautiful park. Blue line is only a few blocks, which gives direct access to O'Hare International Airport. Uber and Lyft are always minutes away, and a Divvy bike station is right around the block. Chicago is a great city to explore. We are in the living breathing heart where locals reside so you’ll get the best the city has to offer!

Guest favorite

A welcoming porch features a wooden deck with white railings and columns. Two chairs are positioned on the porch, accompanied by a barbecue grill nearby. Lush greenery is present, enhancing the outdoor space's natural appeal.

Home in Hyde Park

5 out of 5 average rating, 17 reviews

Amazing historic campus mansion!

This stylish campus mini mansion is perfect for group trips in the historic Hyde Park neighborhood. A cheerful, modern renovation of a historic home, with original woodwork, underfloor bathroom heating and leaded windows. Easy access to Uchicago, the lakefront, Chicago marathon, McCormick trade shows, the Museum of Science & Industry or exploring our vibrant city. Our spotlessly clean property helps you experience everything Chicago has to offer. Hosted by a very experienced all 5 star host.

Guest favorite

Home in Old Town

4.86 out of 5 average rating, 140 reviews

Huge Home *Prime Spot *Yard *Parking *Fireplace

Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost everything Chicago has to offer- Downtown, Magnificent mile, restaurants, bars, boutiques; Lincoln Park and North ave beach from this three-level house. 5 bedrooms, 3.5 baths, 2 fully stocked kitchens, 2 car garage, back yard, laundry, pets welcome - what else can you possibly need? Space is expandable from a smaller family to a group of 22. Message me if you have any questions!

Superhost

A modern kitchen is equipped with stainless steel appliances and white cabinetry. Natural light fills the space through two large windows. A white farmhouse sink is complemented by a dark wooden countertop, while a patterned rug lies on the hardwood floor.

Home in Logan Square

4.83 out of 5 average rating, 101 reviews

California Cottage/4br prime location Logan Square

Incredible location in Logan Square! Walking distance from dozens of restaurants, breweries, bars, nightlife, the square, the farmers’ market and much more. Free street parking in front. 2 blocks from 90/94 and close to the blue line train which goes to many of Chicago’s iconic neighborhoods, downtown, and directly to O’ Hare airport. Beautiful house with high ceilings on the 1st floor. Lovely kitchen with nice appliances. 2 cozy bedrooms upstairs. One with a queen and the other has 3 twins.

Guest favorite

The historic stone façade of the building features intricate architectural details, with large arched windows and a welcoming entrance. Flower pots are displayed on the balcony, and a wrought iron fence surrounds the property, adding to the charm of the exterior.

Apartment in Lake View

4.92 out of 5 average rating, 229 reviews

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Superhost

A cozy seating area is highlighted by two comfortable armchairs, one adorned with a decorative pillow. A coffee table sits centered, decorated with a small plant and decorative trays. Light drapes frame the windows, enhancing the warm atmosphere created by wooden flooring.

Apartment in Hermosa

4.77 out of 5 average rating, 13 reviews

2Level Duplex + Jaccuzi! Gem in Chicago 4BD/3BA

Welcome to our stunning getaway! This luxury duplex is designed to provide comfort & entertainment for your group of up to 8 guests; Indulge in the spacious entertainment area. The backyard is your private oasis, a beautifully landscaped space perfect for gatherings. With 4 lavish bedrooms, a fully equipped kitchen, & modern amenities throughout, your stay here promises both luxury and convenience. Our central location puts you just moments away from the city's finest attractions. Book now!

Guest favorite

Home in West Town

4.94 out of 5 average rating, 35 reviews

Huge Restored Humboldt Park Mansion - Park Views!

Located directly across the street from the huge and gorgeous 200 acre Humboldt Park. This recently restored mansion is an amazing place to bring the whole family with lots of room for gathering together. 5 bedrooms and 3.5 bathrooms ensures that there is plenty of space for all and with a massive public park across the street you can stroll through the park, take a swan boat out on the pond or join a game of soccer or basketball. Easy public transportation and plentiful ubers.

Superhost

A bright living space features a sectional couch positioned around a glass coffee table. Large skylights and windows allow natural light to fill the room, which is accented by a decorative rug and a modern electric fireplace. A television hangs on one wall, displaying a scenic landscape.

Apartment in Logan Square

4.92 out of 5 average rating, 12 reviews

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

The top floor sprawling ranch with duplex down offers sky & outdoors views, privacy, & cathedral ceilings, it is connected to your rear 2nd floor suite with 10ft ceilings. A burgeoning neighborhood next to the 606 Trail Amenities: - Uber-fast Wifi streaming, - Hot tub house - 80" + 75" hi-def tv's - 3 sectional couches - European decor - 2 kitchens - The popular 606 Trail access is 100 ft away, - YMCA across the street with indoor Olympic size & kiddie-pools!

Top guest favorite

A putting green mat is positioned against a tropical-themed mural featuring palm trees and a serene beach. Several golf clubs and three orange practice balls are arranged alongside the mat, creating an inviting space for leisure activities.

Home in Elmhurst

5 out of 5 average rating, 48 reviews

Big Family Home with 4 King Beds

Experience ultimate luxury at our exclusive property. Nestled in a prime location, this meticulously designed retreat offers opulent furnishings, panoramic views, and bespoke amenities. Ideal for discerning travelers and work travelers seeking sophistication and comfort, indulge in a private sanctuary where every detail exceeds expectations. Discover the epitome of elegance with us and create unforgettable memories in this exquisite haven.

Guest favorite

Home in Justice

4.93 out of 5 average rating, 225 reviews

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

3 Kings | 1 Queen | 1 Full | 3 air beds | 2 Pack 'n Plays No charge for: cleaning, extra people, or any other hidden fees. 20% weekly discount applied to 7+ nights. 20% monthly discount. Less than 5 mins to I-294, I-55. 30 mins to Chicago & O'Hare Airport. 15 mins to Midway Airport. 5 mins to Cook County’s forest preserves w/ bike, walking, and horse trails.

Guest favorite

A spacious living area features comfortable leather seating and a modern fan overhead. A sleek entertainment center with a wall-mounted screen is complemented by ambient lighting. Large windows are adorned with deep blue curtains, allowing natural light to filter in, while decorative plants add a touch of greenery.

Apartment in South Shore

5 out of 5 average rating, 17 reviews

Lux 4BR Lakeshore: W/Rftop Book Now!

Indulge in luxury with a 4-bed, 3-bath short-term stay. Enjoy spacious living, serene bedrooms, and elegant bathrooms. Private rooftop oasis for coffee, work functions, or enjoying the night sky. Near Obama Library, immerse in culture, history, golf, and boat outings. Book now for upscale urban living and relaxation in a dynamic locale.

Guest favorite

Home in Wicker Park

4.9 out of 5 average rating, 58 reviews

Downtown Chicago 4Bed Home with Theater & Parking

Welcome to @TheDreamRentals opulent 5-bedroom sanctuary, where luxury meets entertainment in the heart of the city! Nestled in an upscale neighborhood, this exquisite home boasts not only a full-fledged theater but also two stunning rooftop patio decks, making it the perfect choice for your upscale getaway.