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Mansion holiday rentals in Chicago

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Top-rated mansion rentals in Chicago

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Home in Highland Park

4.91 out of 5 average rating, 110 reviews

Rejuvenate and Relax in the North Shore

Set in the midst of an affluent neighborhood, this spacious and sunny four bedroom retreat offers all the comforts of a home away from home. With it's perfect location close to Lake Michigan, Chicago Botanical Garden, Ravinia, Naval Base, and Six Flags Great America to name a few, our family home is within reach to Chicago as well. If you feel very adventurous, just leave your car in garage, pick up a bike and ride the Lake Shore Bike trail all the way to downtown Chicago, enjoying the beautiful scenery. If you feel less adventures but still would like to enjoy beautiful scenery, you can do it by taking a train. Metra can get you downtown Chicago in less than 45 min. and the stop is within walking distance.

Guest favourite

Townhouse in Chicago

4.87 out of 5 average rating, 205 reviews

Prime Reviews a Duplex in Logan Square Chicago

Nestled in a quiet cul-de-sac in Logan Square, this is a serene oasis. Steps away from Milwaukee Ave's renowned restaurants, bars, Revolution Brewery, Stan Mansion, and The Whale, 606 trail, Blue Line to airports and downtown, as well as Bucktown and Wicker Park. Logan Square Public Library a block away. Enjoy a self-check-in process, free street parking, fully-equipped kitchen, 4 BR, 2 baths, and amenities like a washer, dryer, and yard. Please note, per Chicago regulations, no parties allowed.

Guest favourite

Flat in Chicago

4.97 out of 5 average rating, 101 reviews

NorthSide Chicago duplex 5-BD,2King size-free park

Welcome to our luxurious 5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our stunning property is the perfect for your big gathering. Sleeps up to 10 guests with indoor Jacuzzi, full kitchen, free indoor parking, and patio access to grill with big screen TV, and sound system. Keyless check-in and 24/7 active security cameras. Don't miss out on experiencing the best of Chicago from our beautiful and convenient duplex unit. Book your stay now!

Guest favourite

Home in Schaumburg

4.93 out of 5 average rating, 14 reviews

Schaumburg Woodfield Pool House 4bedroom 2.5bath

Freshly updated house with in-ground POOL! Minutes to Woodfield mall and restaurants in Schaumburg. One of the only houses with private pool in the area. LOCATION: 35 min to downtown Chicago, 20 min to O'Hare airport, 20 min to Rosemont convention area MASTER BEDROOM extra large for primary guest(s). Unpack and stay awhile with a large walk in closet. Luxurious attached master bathroom with double sink and large walk in shower with bench. Pool is open from May 14th until the end of September.

Guest favourite

Home in Highland Park

4.93 out of 5 average rating, 40 reviews

Witness Sunrise Over Lake Michigan

Mesmerizing views of Lake Michigan from nearly every corner of this recently renovated Mid-Century Modern home. The house is walking distance from Ravinia Festival, downtown Ravinia Restaurants, and glorious Rosewood Beach; a healthy walk or short drive from Metra Train Stn. to Chicago and from the Chicago Botanical Gardens. Of course, guests can always choose instead to relax fireside, on the roof deck, or at the home’s private beach. Perfect for 4 guests, it accommodates 6. 2K, 2Q, 2.5 baths.

Guest favourite

Home in Schaumburg

4.97 out of 5 average rating, 107 reviews

Modern Spacious Quiet Home Near O'Hare -Deck&Yard

Amazing Modern Big 4 BR 2.5 BA "Aqua' House.Quiet street in the heart of Schaumburg.Upper level:Living Room-TV&Fireplace to cozy up w/h Family.Modern Open Eat-in Kitchen:Custom cabinets,SS Appliances,White Quartz Countertops,breakfast Island.Master suit:King bed&Modern Shower Bath&TV,2nd BR-two full beds,3rd BR-king bed&2nd Modern Tub Bath. Lower Level:Big Family Rom where kids can play,4th BR -king bed&Work Desk,Half bath&Laundry.Big deck&Yard to enjoy w/h family.We have other houses nearby.

Flat in Chicago

4.92 out of 5 average rating, 62 reviews

The Waveland Room 4 Bed/4bath Private Roof-Deck!

"Holy Cow"! 4bed 4bath Duplex Penthouse w/ 3,000 sqft Private Roof-Deck! Step outside & be face-to-face with the iconic Wrigley Field, home of the Chicago Cubs!! This Top floor Duplex-up Penthouse has 4 bedrooms 4 & bathrooms, 2-story Private Penthouse home with a 3,000 sqft PRIVATE Roof Deck. Great open layout w/ Fully-equipped Chef's kitchen, a 20' island fitted with 10 custom bar stools, 8 person dining table, Three 4K UHD TVs In ceiling Surround Sound system (inside and out).

Guest favourite

Home in Chicago

4.87 out of 5 average rating, 135 reviews

Lake View | Wrigley Designer House w/Patio

Between Wrigley Ville and Lincoln Park, our home is on a quiet street. We are surrounded by coffee shops, restaurants and nightlife. There is a Whole Foods less than a block away, a Target and other groceries stores within 5 minutes walk. The house is over 2,500 square feet spread over 3 floors, with 4 completely separate bedrooms. Extra tall ceilings in the common areas, artsy cathedral ceilings and skylights in the upstairs bedrooms and very comfortable mattresses will help you unwind.

Guest favourite

Home in Chicago

5.0 out of 5 average rating, 53 reviews

Architect's Urban Oasis | 4bd/3ba I Luxe

Experience our one-of-a-kind home in the heart of downtown Chicago. It has 4 bedrooms, 3 bathrooms and comfortably sleeps 8. We are offering our home to select people visiting Chicago. Perfect for families and mature groups. I am an architect, and designed this home for my family in 2005. It was published in Chicago Magazine, Playboy, and featured in several TV commercials. Chosen by CS as the most luxurious AirBnb in Chicago in 2023. STRICT NO PARTY, EVENTS or EXTRA GUESTS policy.

Guest favourite

Flat in Chicago

4.96 out of 5 average rating, 237 reviews

Spacious 5-BR home next to transit! Great area!

A modern fully furnished apartment in Chicago located in the heart of Logan Square. Offering endless options for dining, entertainment, culture, and transportation all within a walkable neighborhood. Walk or Train to every site in minutes; PARKING PASSES INCLUDED! *** We are literally a minute away from the center of Logan Square and Transit. *** This is not a single-family home. It is an apartment with another tenant in the building. Outdoor spaces are shared with the other tenant.

Guest favourite

Home in Highland Park

4.91 out of 5 average rating, 127 reviews

2-Acre Highland Park Retreat with Heated Pool ~ 5*

Experience luxury of this award winning 6BR 4Bath family home in picturesque Northshore private estate. Spend day by the private heated pool, enjoy beauty of gardens, explore local landmarks, starting with the gates of neighborhood Michael Jordan estate. The stylish design and rich amenity list will leave you in awe. ✔ Two-Acre Estate ✔ 6 Comfy BRs ✔ Multiple Living Areas ✔ Full Kitchen ✔ Backyard (Pool, Lounges, BBQ) ✔ Smart TVs ✔ High-Speed Wi-Fi ✔ Free Parking See more below!

Guest favourite

Apartment in Chicago

5.0 out of 5 average rating, 104 reviews

Spacious 4 Bedroom Condo

Located in West Town in the heart of Noble Square, just north of West Loop with access to all the best restaurants and only minutes away from River North and Old town, enjoy this 4 bedroom, 3.5 bath condo with private parking, 2 living spaces, heated floors throughout the entire lower level and steam showers. A gourmet kitchen stocked with everything you will need including an espresso maker. This home is perfect for families, couples, friends or traveling for business.

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Popular amenities for Chicago mansion rentals

Free parking on premises

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Luxury mansion rentals

Guest favourite

Apartment in Chicago

4.95 out of 5 average rating, 132 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Guest favourite

Home in Chicago

4.93 out of 5 average rating, 212 reviews

Luxe 6BR House *Trendy Logan Square *Garage Access

Guest favourite

Apartment in Chicago

4.98 out of 5 average rating, 126 reviews

Luxury 4 bedroom steps from Wrigley

Guest favourite

Apartment in Chicago

4.94 out of 5 average rating, 125 reviews

711 The Penthouse

Guest favourite

Flat in Chicago

4.93 out of 5 average rating, 134 reviews

❤️ Lowest Rates! Spacious Duplex with Parking!

Flat in Chicago

4.86 out of 5 average rating, 169 reviews

Impeccable 5-Bed Wrigleville Beauty

Home in Chicago

4.9 out of 5 average rating, 162 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Apartment in Chicago

4.82 out of 5 average rating, 188 reviews

Chicago River West 4 Bedroom / 3 Bathroom

Pet-friendly mansion rentals

Guest favourite

Home in Chicago

4.82 out of 5 average rating, 139 reviews

Historic Old Town, Fabulous 4 Bedroom Home

Guest favourite

Home in Chicago

4.98 out of 5 average rating, 132 reviews

Southwestern Penthouse TRES | Sleeps 12

Flat in Chicago

4.82 out of 5 average rating, 278 reviews

Stylish Comfy Flat by Wrigley Field+CTA for Groups

Apartment in Chicago

4.79 out of 5 average rating, 108 reviews

Spacious Home, Incredible Lakeview Location

Flat in Chicago

4.86 out of 5 average rating, 155 reviews

*Comfortable & Spacious Home Close to Downtown*

Flat in Chicago

4.83 out of 5 average rating, 255 reviews

4BDRM Gorgeous Apt Pilsen Private Parking avail

Guest favourite

Townhouse in Chicago

4.84 out of 5 average rating, 150 reviews

Downtown Elegance ✨ Private Yard Parking

Guest favourite

Flat in Chicago

4.98 out of 5 average rating, 52 reviews

4 BR Mayfair flat

Mansion rentals with a pool

Home in Schaumburg

5.0 out of 5 average rating, 4 reviews

Paradise 4BR w/ Pool & Games

Guest favourite

Home in Glen Ellyn

4.94 out of 5 average rating, 17 reviews

Glen Ellyn Home

Guest favourite

Yurt in Homewood

4.97 out of 5 average rating, 74 reviews

Glamping Yurt&RV Game Room Pool/Hot Tub/Sauna plus

Flat in Chicago

5.0 out of 5 average rating, 4 reviews

Luxe 2-Level PH + Spa House Retreat! Pets Welcome

Home in Lake Forest

4.91 out of 5 average rating, 58 reviews

Beautiful 137 Year Old Farm Home (3night min)

Flat in Chicago

4.62 out of 5 average rating, 50 reviews

Stylish 4 Bedroom / 4 bath in the Loop | Sleeps 12

Flat in Chicago

Cloud9 | Up to 15ppl|Balcony @MagMile |The Apollo

Home in Chicago Heights

Olympia field -matteson IL- homewood, park forest

Destinations to explore