Mansion vacation rentals in Chicago

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!

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.

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

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.

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!

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.

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.

Luxury Retreat with Home Theater

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.

Luxury River West Townhome with Garage

Exquisitely decorated 4 BR home located one O'Hare Blue Line El stop from the Loop (downtown Chicago). Accommodates up to 8. Private drive-in courtyard and private in-unit garage. Unique features include rooftop deck, large jacuzzi in master bath, hand-made Yamaha grand piano for qualified musicians.