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
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Home in Schaumburg
5 out of 5 average rating, 6 reviewsParadise 4BR w/ Pool & Games
Yurt in Homewood
4.97 out of 5 average rating, 77 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Home in Glen Ellyn
4.94 out of 5 average rating, 18 reviewsGlen Ellyn Home
Home in Lake Forest
4.91 out of 5 average rating, 58 reviewsBeautiful 137 Year Old Farm Home (3night min)
Rental unit in The Loop
4.6 out of 5 average rating, 52 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Rental unit in Near North Side
New place to stayCloud9|Golf,Gym,CoWorking@LincolnPark|The Ash
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Luxury mansion rentals
Condo in Logan Square
4.95 out of 5 average rating, 133 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Townhouse in West Town
4.95 out of 5 average rating, 198 reviewsLuxury River West Townhome with Garage
Home in Wrigleyville
4.9 out of 5 average rating, 162 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Condo in Wrigleyville
4.98 out of 5 average rating, 130 reviewsLuxury 4 bedroom steps from Wrigley
Home in Logan Square
4.97 out of 5 average rating, 100 reviewsThe Hamlin In Logan Square 4BR/2BA w/Parking!
Condo in West Town
4.94 out of 5 average rating, 126 reviews711 The Penthouse
Rental unit in Wrigleyville
4.86 out of 5 average rating, 170 reviewsImpeccable 5-Bed Wrigleville Beauty
Home in Logan Square
5 out of 5 average rating, 18 reviewsLux LoganHouse w/garage, Sleeps 12, & rooftop deck
Pet-friendly mansion rentals
Home in Highland Park
4.91 out of 5 average rating, 114 reviewsRejuvenate and Relax in the North Shore
Home in Logan Square
4.98 out of 5 average rating, 135 reviewsSouthwestern Penthouse TRES | Sleeps 12
Rental unit in Lake View
4.81 out of 5 average rating, 278 reviewsSophisticated, Historic & Comfy Flat near Wrigley!
Townhouse in West Town
4.93 out of 5 average rating, 99 reviewsUpscale 4-Bedroom Townhouse w/Garage - LOCATION
Rental unit in West Town
4.85 out of 5 average rating, 157 reviews*Comfortable & Spacious Home Close to Downtown*
Rental unit in Irving Park
4.8 out of 5 average rating, 185 reviewsBright & Renovated Irving Park Duplex W/ Backyard!
Townhouse in Uptown
4.97 out of 5 average rating, 126 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Home in West Ridge
4.93 out of 5 average rating, 107 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Destinations to explore
- Downtown Chicago Vacation rentals
- Milwaukee Vacation rentals
- Lake Geneva Vacation rentals
- Lake Michigan Beach Vacation rentals
- Saugatuck Vacation rentals
- Evanston Vacation rentals
- Holland Vacation rentals
- South Haven Vacation rentals
- Naperville Vacation rentals
- South Side Vacation rentals
- South Bend Vacation rentals
- Schaumburg Vacation rentals
- Rentals with an accessible height bed Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Kid-friendly rentals Chicago
- Bed and breakfasts Chicago
- Smoking-friendly rentals Chicago
- Rentals with a patio Chicago
- Private suite rentals Chicago
- Beachfront rentals Chicago
- Apartment rentals Chicago
- Townhouse rentals Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a sauna Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Monthly Rentals Chicago
- Rentals with lake access Chicago
- House rentals Chicago
- Rentals with an EV charger Chicago
- Lakehouse rentals Chicago
- Rentals with a washer and dryer Chicago
- Fitness-friendly rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with beach access Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Waterfront rentals Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Mansion rentals Milwaukee
- Mansion rentals Illinois
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom