Mansion vacation rentals in Chicago
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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
Luxury mansion rentals
Condo in Chicago
4.95 out of 5 average rating, 132 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Condo in Chicago
4.98 out of 5 average rating, 127 reviewsLuxury 4 bedroom steps from Wrigley
Home in Chicago
4.9 out of 5 average rating, 162 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Apartment in Chicago
4.86 out of 5 average rating, 169 reviewsImpeccable 5-Bed Wrigleville Beauty
Apartment in Chicago
4.93 out of 5 average rating, 134 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Condo in Chicago
4.79 out of 5 average rating, 109 reviewsSpacious Home, Incredible Lakeview Location
Condo in Chicago
4.82 out of 5 average rating, 188 reviewsChicago River West 4 Bedroom / 3 Bathroom
Townhouse in Chicago
4.97 out of 5 average rating, 125 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Pet-friendly mansion rentals
Home in Chicago
4.98 out of 5 average rating, 132 reviewsSouthwestern Penthouse TRES | Sleeps 12
Home in Chicago
4.82 out of 5 average rating, 139 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Apartment in Chicago
4.81 out of 5 average rating, 280 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Home in Chicago
4.93 out of 5 average rating, 106 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Apartment in Chicago
4.86 out of 5 average rating, 155 reviews*Comfortable & Spacious Home Close to Downtown*
Home in Oakbrook Terrace
4.82 out of 5 average rating, 38 reviewsDesirable chic home in a Prime Location!
Apartment in Chicago
4.98 out of 5 average rating, 53 reviews4 BR Mayfair flat
Townhouse in Chicago
4.84 out of 5 average rating, 44 reviewsLarge Executive Row house in Historic Pullman
Mansion rentals with a pool
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Yurt in Homewood
4.97 out of 5 average rating, 75 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Apartment in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Apartment in Chicago
5.0 out of 5 average rating, 3 reviewsCloud9 | Up to 15 ppl Millenium Park | The Jordan
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Destinations to explore
- Downtown Chicago Vacation rentals
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