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.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago mansion rentals
Luxury mansion rentals
Apartment in Chicago
4.98 out of 5 average rating, 129 reviewsLuxury 4 bedroom steps from Wrigley
Home in Chicago
4.97 out of 5 average rating, 100 reviewsThe Hamlin In Logan Square 4BR/2BA w/Parking!
Apartment in Chicago
4.82 out of 5 average rating, 131 reviewsMassive Old Town Home Steps to Wells St & Beach
Home in Chicago
4.9 out of 5 average rating, 162 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Townhouse in Chicago
4.95 out of 5 average rating, 98 reviewsUpscale 4-Bedroom Townhouse w/Garage - LOCATION
Apartment in Chicago
4.82 out of 5 average rating, 189 reviewsChicago River West 4 Bedroom / 3 Bathroom
Flat in Chicago
4.86 out of 5 average rating, 170 reviewsImpeccable 5-Bed Wrigleville Beauty
Home in Chicago
5.0 out of 5 average rating, 18 reviewsLux LoganHouse w/garage, Sleeps 12, & rooftop deck
Pet-friendly mansion rentals
Home in Glen Ellyn
4.9 out of 5 average rating, 99 reviewsHome in Glen Ellyn
Home in Chicago
4.98 out of 5 average rating, 133 reviewsSouthwestern Penthouse TRES | Sleeps 12
Apartment in Chicago
4.79 out of 5 average rating, 110 reviewsSpacious Home, Incredible Lakeview Location
Flat in Chicago
4.81 out of 5 average rating, 278 reviewsSophisticated, Historic & Comfy Flat near Wrigley!
Townhouse in Chicago
4.97 out of 5 average rating, 125 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Home in Chicago
4.96 out of 5 average rating, 24 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
Home in Schaumburg
4.83 out of 5 average rating, 35 reviewsRadiance - Single Level Home
Home in Skokie
5.0 out of 5 average rating, 27 reviewsLuxury Home - Pool Tbl/Bar/Patio
Mansion rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Schaumburg
5.0 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Yurt in Homewood
4.97 out of 5 average rating, 77 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Flat in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Flat in Chicago
4.89 out of 5 average rating, 9 reviewsDTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)
Flat in Chicago
4.6 out of 5 average rating, 52 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Flat in Chicago
5.0 out of 5 average rating, 3 reviewsCloud9 | Up to 15 ppl Millenium Park | The Jordan
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- New Buffalo Holiday rentals
- Family-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Lakehouse rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a patio Chicago
- Monthly Rentals Chicago
- Rentals with an accessible-height bed Chicago
- Private suite rentals Chicago
- Family-friendly rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Loft rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a sauna Chicago
- Rentals with a balcony Chicago
- Rentals with an EV charger Chicago
- House rentals Chicago
- Beachfront rentals Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Flat rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with lake access Chicago
- Waterfront rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Townhouse rentals Chicago
- Mansion rentals Milwaukee
- Mansion rentals Illinois
- Yurt Rentals United States
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- Farm Cottages United Kingdom
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