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, 127 reviewsLuxury 4 bedroom steps from Wrigley
Townhouse in Chicago
4.95 out of 5 average rating, 196 reviewsLuxury River West Townhome with Garage
Home in Chicago
4.9 out of 5 average rating, 162 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Flat in Chicago
4.93 out of 5 average rating, 134 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Flat in Chicago
4.86 out of 5 average rating, 169 reviewsImpeccable 5-Bed Wrigleville Beauty
Flat in Chicago
4.8 out of 5 average rating, 184 reviewsBright & Renovated Irving Park Duplex W/ Backyard!
Townhouse in Chicago
4.97 out of 5 average rating, 125 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Home in Chicago
5.0 out of 5 average rating, 54 reviewsArchitect's Urban Oasis | 4bd/3ba I Luxe
Pet-friendly mansion rentals
Apartment in Chicago
4.79 out of 5 average rating, 109 reviewsSpacious Home, Incredible Lakeview Location
Apartment in Chicago
4.82 out of 5 average rating, 188 reviewsChicago River West 4 Bedroom / 3 Bathroom
Flat in Chicago
4.81 out of 5 average rating, 280 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Home in Chicago
4.82 out of 5 average rating, 139 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Home in Chicago
4.93 out of 5 average rating, 106 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Home in Oakbrook Terrace
4.82 out of 5 average rating, 38 reviewsDesirable chic home in a Prime Location!
Flat 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
4.93 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
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
4.62 out of 5 average rating, 50 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Home in Schaumburg
4.33 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Flat in Chicago
Cloud9|2x1 apartments @Fulton Market|The Pop
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
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Townhouse rentals Chicago
- Bed and breakfasts Chicago
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- House rentals Chicago
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- Private suite rentals Chicago
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- Monthly Rentals Chicago
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- Mansion rentals Milwaukee
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- Yurt Rentals United States
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