
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

Home in West Town
4.97 out of 5 average rating, 95 reviewsRelax with Family in a Luxury Chicago Single Family Home

Flat in Lake View
4.82 out of 5 average rating, 326 reviewsSophisticated, Historic & Comfy Flat near Wrigley!

Townhouse in West Town
4.96 out of 5 average rating, 69 reviewsBeautiful Spacious RiverWest Townhome 4-Bed/4-Bath

Home in South Shore
5 out of 5 average rating, 9 reviewsLuxury 4-Bedroom Retreat, Near Lakefront

Home in Oak Park
4.94 out of 5 average rating, 47 reviewsOak Park 3000 sq ft, sleeps 16

Apartment in Wrigleyville
4.99 out of 5 average rating, 152 reviewsLuxury 4 bedroom steps from Wrigley

Townhouse in West Loop
4.99 out of 5 average rating, 241 reviewsSpacious 4-Level/4-Bedroom Townhouse in West Loop

Home in Bolingbrook
5 out of 5 average rating, 12 reviewsCosmos Home, Hot Tub, King Beds, 5 bed, 4 baths
Pet-friendly mansion rentals

Home in Berwyn
4.92 out of 5 average rating, 26 reviewsEuropean Custom Built Home

Home in Downers Grove
4.89 out of 5 average rating, 35 reviewsLuxury Bliss: Opulent 5BR/3.5BA Delightful Escape

Home in Schaumburg
4.8 out of 5 average rating, 80 reviewsSpacious 5 Bedroom 1 Level Renovated Modern House

Home in Evanston
5 out of 5 average rating, 4 reviewsCozy Private & Spacious Duplex

Home in Chicago
4.93 out of 5 average rating, 86 reviewsSpacious Row Home next to Transit w Garage

Home in Romeoville
5 out of 5 average rating, 11 reviewsRejuvenate: 4BR, fenced yard

Home in Lombard
4.67 out of 5 average rating, 3 reviewsCheerful Chicago-area 5 Bedroom Oasis

Home in Addison
4.96 out of 5 average rating, 72 reviewsHome in Unincorporated Addison. RV & Pet Friendly
Mansion rentals with a pool

Flat in The Loop
4.86 out of 5 average rating, 14 reviewsDTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)

Home in Munster
5 out of 5 average rating, 10 reviewsMunster hide away

Home in Bloomingdale
4.95 out of 5 average rating, 43 reviewsWhole House with a Hot Tub!

Flat in The Loop
4.33 out of 5 average rating, 3 reviewsCloud9 | Downtown near the Bean w/Gym |The Winfrey

Home in Austin
New place to stay4Bed GemW/Pool for8 Near ORD/MDW

Cabin in New Lenox
4.57 out of 5 average rating, 61 reviewsYour favorite vacation spot

Flat in The Loop
4.64 out of 5 average rating, 59 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

Home in Glenwood
4.8 out of 5 average rating, 55 reviewsSpacious Family Glenwood Estates Home w/ Hot Tub!
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- West Side Holiday rentals
- North Side Holiday rentals
- South Bend Holiday rentals
- Lake Michigan Beach Holiday rentals
- South Side Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
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- Private suite rentals Chicago
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