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
Schaumburg Woodfield Pool House 4bedroom 2.5bath
Yurt in Homewood
Glamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Rental unit in Logan Square
Luxe 2-Level PH + Spa House Retreat! Pets Welcome
Rental unit in The Loop
DTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)
Rental unit in The Loop
Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Rental unit in West Loop
Cloud9|2x1 apartments @Fulton Market|The Pop
Home in Chicago Heights
Olympia field -matteson IL- homewood, park forest
Cabin in New Lenox
Your favorite vacation spot
Luxury mansion rentals
Condo in Logan Square
The Grand Kimball Lodge, Logan Square, Sleeps 14
Condo in Andersonville
Warm & Comforting 4br/2ba In Andersonville
Condo in Wrigleyville
Luxury 4 bedroom steps from Wrigley
Condo in West Town
711 The Penthouse
Home in Logan Square
The Hamlin In Logan Square 4BR/2BA w/Parking!
Condo in Lincoln Park
Massive Old Town Home Steps to Wells St & Beach
Home in Wrigleyville
Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Condo in West Town
Chicago River West 4 Bedroom / 3 Bathroom
Pet-friendly mansion rentals
Rental unit in Uptown
❤️ Lowest Rates! Spacious Duplex with Parking!
Home in Highland Park
Rejuvenate and Relax in the North Shore
Rental unit in Lake View
Stylish Comfy Flat by Wrigley Field+CTA for Groups
Home in Logan Square
Southwestern Penthouse TRES | Sleeps 12
Townhouse in West Town
Upscale 4-Bedroom Townhouse w/Garage - LOCATION
Condo in Lake View
Spacious Home, Incredible Lakeview Location
Home in West Ridge
Luxury House 6BED/2.5BATH/4PARKING close to lake
Townhouse in Old Town
Downtown Elegance ✨ Private Yard Parking
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
- New Buffalo Vacation rentals
- Rentals with a sauna Chicago
- Kid-friendly rentals Chicago
- Loft rentals Chicago
- Lakehouse rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a washer and dryer Chicago
- Family-friendly rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Rentals with lake access Chicago
- Fitness-friendly rentals Chicago
- Rentals with a balcony Chicago
- Monthly Rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with an accessible height bed Chicago
- Waterfront rentals Chicago
- Rentals with an EV charger Chicago
- Private suite rentals Chicago
- Rentals with a patio Chicago
- Rentals with beach access Chicago
- Rentals with a home theater Chicago
- Rentals with outdoor seating Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Bed and breakfasts Chicago
- Beachfront rentals Chicago
- Apartment rentals Chicago
- Rentals with pools Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Townhouse rentals Chicago
- House rentals Chicago
- Mansion rentals Milwaukee
- Mansion rentals Illinois
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- 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
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes