Mansion holiday rentals in Willowbrook

711 The Penthouse

Luxurious upscale Duplex Penthouse-River West neighborhood in downtown Chicago! Newly rehabbed and updated interior design that is mind blowing. Over 5600 sq ft. Features 5 bedrooms, 2.5 baths, 3 largeTVs with sonos sound system, game room!!. Near CTA Blue Line, close to the best dining and attractions of Chicago! Two large living areas perfect for hosting small events, bachelor(ette) parties, bridal or baby showers, work/travel, and family reunions. Rooftop with beautiful view of the skyline!

Stone Mansion Sleeps 10-20 Free parking & TV

Giant, 4 bedroom, 2,300 square feet apartment on 2nd floor, near Red Line Train, bars, cafe's, shopping, restaurants, Lakefront and everything else Chicago has to offer. Large living room with bar area, TV and fridge for socializing before hitting the town. Dining room has a large table and 8 chairs. 4 bedrooms with 2 private rooms with king beds and one with a double bed. 4 futons for in the living room for extra sleeping space two (2) parking spots in the west facing garage on premises.

Massive Old Town Home Steps to Wells St & Beach

Start your Windy City adventures in my spacious 3rd-floor duplex in the heart of Chicago's vibrant Old Town neighborhood! This 8 bed, 4 bath home comfortably sleeps up to 20 guests, making it perfect for large groups or families. Enjoy modern furnishings, a fully equipped kitchen and two cozy living areas to relax in after exploring the city. Steps from popular restaurants, bars, boutiques and the lake, you’ll be immersed in local charm. (Please note, parties and large events are not allowed)

WATER FRONT LUXURY HOME WILL FEEL LIKE A RESORT!

LUXURY HOME WITH A SPECTACULAR VIEW OF THE WATER. EXECUTIVE BRICK HOME WITH BRAZILIAN CHERRY-HARD WOOD FLOORS. FLOOR TO CEILING WINDOWS IN FAMILY ROOM WITH 14' CEILINGS/DECORATIVE BRICK FIREPLACE. GOURMET KITCHEN W/ MAPLE CABINETS/GRANITE & SS APPS/EATING ISLAND. SUNROOM WITH BEAUTIFUL VIEW OF POND. LUXURY MASTER SUITE W/ LUXURY BATH. FULL FINISHED BASEMENT WITH 9' FOOT CEILINGS INC FULL BATH & BED. TRANQUIL BRICK PAVER PATIO. (Plus 100-acre park, paths, soccer & baseball fields, & more).

Luxury 5BR Mansion, Gym, & Backyard Oasis

Welcome to our luxurious 5-bedroom, 4.5-bathroom mansion. You'll fall in love with the elegance of this 8800 sft property, which comfortably accommodates up to 10 guests. With a gym, a garage for your convenience, a backyard fire pit for cozy evenings, and a basement designed for entertainment, this Airbnb offers the ultimate retreat for relaxation and fun. Whether you're seeking a family reunion, a getaway with friends, or a peaceful escape, this mansion is your perfect destination.

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!

Historic Old Town, Fabulous 4 Bedroom Home

Lovely Historic 4 Bedroom, 3 bathroom home in Old Town, walking distance of restaurants, boutiques, coffee shops, the lake front and excellent public transportation. 2nd Fl. Master Bedroom has a King size bed and Twin plus private bath with bathtub, walk in shower, w/d; 2nd Fl. two room "suite" with a Queen size bed in each room and private bathroom. 1st Fl. bedroom with Queen bed and private bathroom. Off Street Parking and Private Deck! License Pending.

Bayless Dune Lodge at West Beach - Indiana Dunes!

Bayless Dune Lodge at West Beach is a gorgeous, Lodge-themed home in Miller Beach, Indiana, a scenic community surrounded by the Indiana Dunes National Park! A short walk to one of the finest white sand beaches on Lake Michigan, the Lodge sits on nearly half an acre of land nestled into the "Bayless Dunes Nature Preserve." The property boasts a heated, in-ground swimming pool, pool-side lounge area, two outdoor dining areas, two spa-quality bathrooms and more!

Luxurious Home - Golf Courses, Theater, Spa & Gym

See Video Tour with VR Code in Photo. Area Luxurious custom home on Tanna Farms Golf Course with stunning views and upscale features. Enjoy a gourmet kitchen, home theater, game room, steam shower, and spa-like primary suite. Relax in the 8–10 person hot tub or entertain in the spacious family room. Includes full gym, smart home tech, and new HVAC. Near METRA, trails, tennis, and two 18-hole golf courses. Perfect for families, golf getaways, and group stays.