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
4.95 out of 5 average rating, 129 reviewsThe Grand Kimball Lodge, Logan Square, Sleeps 14
Home in Chicago
4.93 out of 5 average rating, 211 reviewsLuxe 6BR House *Trendy Logan Square *Garage Access
Apartment in Chicago
4.94 out of 5 average rating, 124 reviews711 The Penthouse
Flat in Chicago
4.92 out of 5 average rating, 133 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Apartment in Chicago
4.98 out of 5 average rating, 125 reviewsLuxury 4 bedroom steps from Wrigley
Flat in Chicago
4.86 out of 5 average rating, 168 reviewsImpeccable 5-Bed Wrigleville Beauty
Townhouse in Chicago
4.97 out of 5 average rating, 122 reviews*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*
Flat in Chicago
4.86 out of 5 average rating, 155 reviews*Comfortable & Spacious Home Close to Downtown*
Pet-friendly mansion rentals
Home in Chicago
4.82 out of 5 average rating, 140 reviewsHistoric Old Town, Fabulous 4 Bedroom Home
Apartment in Chicago
4.79 out of 5 average rating, 107 reviewsSpacious Home, Incredible Lakeview Location
Flat in Chicago
4.82 out of 5 average rating, 276 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Home in Bensenville
4.87 out of 5 average rating, 63 reviewsThe Skyway - 5+beds
Home in Chicago
5.0 out of 5 average rating, 13 reviewsModern Family Townhouse
Home in Burbank
4.9 out of 5 average rating, 21 reviewsKing bed, Free Wi-Fi, Burbank
Home in Chicago
5.0 out of 5 average rating, 21 reviews4BD/4BTH - Entire Building+Garage - Wicker Park!
Home in Addison
5.0 out of 5 average rating, 28 reviewsHome in Unincorporated Addison. RV & Pet Friendly
Mansion rentals with a pool
Home in Schaumburg
5.0 out of 5 average rating, 3 reviewsParadise 4BR w/ Pool & Games
Home in Glen Ellyn
4.94 out of 5 average rating, 17 reviewsGlen Ellyn Home
Flat in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Yurt in Homewood
4.97 out of 5 average rating, 74 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Flat in Chicago
4.61 out of 5 average rating, 49 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Flat in Chicago
New place to stayCloud9|Golf,Gym,CoWorking@LincolnPark|The Ash
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 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
- Fitness-friendly rentals Chicago
- Rentals with lake access Chicago
- Rentals with an accessible-height bed Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with an EV charger Chicago
- Rentals with a cinema Chicago
- Rentals with outdoor seating Chicago
- Flat rentals Chicago
- Rentals with a sauna Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a firepit Chicago
- Loft rentals Chicago
- Family-friendly rentals Chicago
- Beachfront rentals Chicago
- Townhouse rentals Chicago
- Rentals with beach access Chicago
- Rentals with pools Chicago
- Rentals with a fireplace Chicago
- Boutique hotel rentals Chicago
- Guest house rentals Chicago
- Bed and breakfasts Chicago
- House rentals Chicago
- Apartment rentals Chicago
- Rentals with a hot tub Chicago
- Private suite rentals Chicago
- Monthly Rentals Chicago
- Rentals with a balcony Chicago
- Rentals with a patio Chicago
- Waterfront rentals Chicago
- Smoking-friendly rentals Chicago
- Lakehouse rentals Chicago
- Family-friendly rentals 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