Mansion vacation 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.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Chicago mansion rentals
Mansion rentals with a pool
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Nov 21 – 28
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Nov 14 – 21
Home in Glen Ellyn
4.94 out of 5 average rating, 16 reviewsGlen Ellyn Home
Jul 23 – 30
Apartment in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Oct 23 – 30
Yurt in Homewood
4.97 out of 5 average rating, 74 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Apr 19 – 26
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Apr 8 – 15
Apartment in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Mar 11 – 18
Apartment in Chicago
New place to stayCloud9|Near Millenium Park|The Poppy
Jan 23 – 30
Luxury mansion rentals
Condo in Chicago
4.95 out of 5 average rating, 129 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Dec 5 – 12
Apartment in Chicago
4.92 out of 5 average rating, 133 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Jul 12 – 19
Condo in Chicago
4.98 out of 5 average rating, 123 reviewsLuxury 4 bedroom steps from Wrigley
Dec 15 – 22
Apartment in Chicago
4.86 out of 5 average rating, 166 reviewsImpeccable 5-Bed Wrigleville Beauty
Oct 9 – 16
Home in Chicago
4.9 out of 5 average rating, 160 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Jul 23 – 30
Condo in Chicago
4.82 out of 5 average rating, 187 reviewsChicago River West 4 Bedroom / 3 Bathroom
Mar 11 – 18
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Sep 25 – Oct 2
Home in Chicago
5.0 out of 5 average rating, 10 reviewsLuxe & Modern House + Skyline Rooftop! Sleeps 10
Jan 31 – Feb 7
Pet-friendly mansion rentals
Condo in Chicago
4.79 out of 5 average rating, 107 reviewsSpacious Home, Incredible Lakeview Location
Oct 30 – Nov 6
Apartment in Chicago
4.82 out of 5 average rating, 275 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Oct 22 – 29
Apartment in Chicago
4.86 out of 5 average rating, 154 reviews*Comfortable & Spacious Home Close to Downtown*
Jun 29 – Jul 6
Townhouse in Chicago
4.84 out of 5 average rating, 150 reviewsDowntown Elegance ✨ Private Yard Parking
Oct 25 – Nov 1
Home in Chicago
5.0 out of 5 average rating, 20 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
Nov 26 – Dec 3
Home in Lombard
4.95 out of 5 average rating, 57 reviewsImagine… 5 Brs/ Game Room
Dec 7 – 14
Townhouse in Chicago
4.86 out of 5 average rating, 43 reviewsLarge Executive Row house in Historic Pullman
Dec 10 – 17
Home in Addison
5.0 out of 5 average rating, 28 reviewsHome in Unincorporated Addison. RV & Pet Friendly
Aug 19 – 26
Destinations to explore
- Downtown Chicago Vacation rentals
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