Mansion holiday rentals in Chicago
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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
Condo in Chicago
4.91 out of 5 average rating, 148 reviewsWarm & Comforting 4br/2ba In Andersonville
Condo in Chicago
4.98 out of 5 average rating, 129 reviewsLuxury 4 bedroom steps from Wrigley
Apartment in Chicago
4.93 out of 5 average rating, 135 reviews❤️ Lowest Rates! Spacious Duplex with Parking!
Condo in Chicago
4.94 out of 5 average rating, 126 reviews711 The Penthouse
Home in Chicago
4.97 out of 5 average rating, 100 reviewsThe Hamlin In Logan Square 4BR/2BA w/Parking!
Condo in Chicago
4.82 out of 5 average rating, 131 reviewsMassive Old Town Home Steps to Wells St & Beach
Home in Chicago
4.9 out of 5 average rating, 162 reviewsSoaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP
Townhouse in Chicago
4.95 out of 5 average rating, 98 reviewsUpscale 4-Bedroom Townhouse w/Garage - LOCATION
Pet-friendly mansion rentals
Home in Highland Park
4.91 out of 5 average rating, 113 reviewsRejuvenate and Relax in the North Shore
Home in Chicago
4.98 out of 5 average rating, 133 reviewsSouthwestern Penthouse TRES | Sleeps 12
Apartment in Chicago
4.81 out of 5 average rating, 280 reviewsStylish Comfy Flat by Wrigley Field+CTA for Groups
Condo in Chicago
4.79 out of 5 average rating, 110 reviewsSpacious Home, Incredible Lakeview Location
Townhouse in Chicago
4.84 out of 5 average rating, 152 reviewsDowntown Elegance ✨ Private Yard Parking
Home in Chicago
4.93 out of 5 average rating, 107 reviewsLuxury House 6BED/2.5BATH/4PARKING close to lake
Home in Oakbrook Terrace
4.82 out of 5 average rating, 39 reviewsDesirable chic home in a Prime Location!
Home in Oak Forest
4.93 out of 5 average rating, 58 reviewsMy Prima Karina 4bd 2ba in Chicago Suburbs
Mansion rentals with a pool
Home in Schaumburg
4.93 out of 5 average rating, 14 reviewsSchaumburg Woodfield Pool House 4bedroom 2.5bath
Yurt in Homewood
4.97 out of 5 average rating, 77 reviewsGlamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus
Apartment in Chicago
5.0 out of 5 average rating, 4 reviewsLuxe 2-Level PH + Spa House Retreat! Pets Welcome
Apartment in Chicago
4.89 out of 5 average rating, 9 reviewsDTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)
Apartment in Chicago
4.6 out of 5 average rating, 52 reviewsStylish 4 Bedroom / 4 bath in the Loop | Sleeps 12
Apartment in Chicago
Cloud9|2x1 apartments @Fulton Market|The Pop
Home in Carol Stream
4.55 out of 5 average rating, 20 reviewsAmazing Summer Pool Awaits You!
Cabin in New Lenox
4.61 out of 5 average rating, 41 reviewsYour favorite vacation spot
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
- Family-friendly rentals Chicago
- Fitness-friendly rentals Chicago
- Hotel rentals Chicago
- Pet-friendly rentals Chicago
- Rentals with pools Chicago
- Rentals with beach access Chicago
- Lakehouse rentals Chicago
- Bed and breakfasts Chicago
- Rentals with a patio Chicago
- Monthly Rentals Chicago
- Rentals with an accessible height bed Chicago
- Private suite rentals Chicago
- Kid-friendly rentals Chicago
- Condo rentals Chicago
- Rentals with a hot tub Chicago
- Loft rentals Chicago
- Boutique hotel rentals Chicago
- Rentals with a fireplace Chicago
- Rentals with a sauna Chicago
- Rentals with a balcony Chicago
- Rentals with an EV charger Chicago
- House rentals Chicago
- Beachfront rentals Chicago
- Rentals with a home theatre Chicago
- Rentals with outdoor seating Chicago
- Apartment rentals Chicago
- Smoking-friendly rentals Chicago
- Rentals with a washing machine and dryer Chicago
- Rentals with lake access Chicago
- Waterfront rentals Chicago
- Rentals with breakfast Chicago
- Rentals with a fire pit Chicago
- Townhouse rentals Chicago
- Mansion rentals Milwaukee
- Mansion rentals Illinois
- Yurt Rentals United States
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