Mansion vacation rentals in Wrigleyville

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Top-rated mansion rentals in Wrigleyville

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Guest favorite

A private outdoor patio space is presented, featuring a metal table with four matching chairs under a canopy. A grill is positioned nearby, and vibrant flower arrangements adorn the area. Lush green grass is visible, bordered by a wooden fence and trees, creating a tranquil setting.

Apartment in Lincoln Square

4.8 out of 5 average rating, 238 reviews

Spacious 4 bedroom North side Apt / Parking

Gather with friends and family in this 2-story 4 bedroom second floor apt. Where you will find plenty of space for your group to spread out and enjoy Chicago under one roof. The kitchen is spacious, loaded with amenities and the living room is a great space for a movie night or games. Its in a great location, too! Walkable to Lincoln ave with all the restaurants and bars Lincoln Square has to offer, and close to public trans Amazing location for a summer FAMILY TRIP or gathering of friends.

Guest favorite

The living area features high ceilings and large windows, allowing natural light to illuminate the space. A cozy sectional sofa is positioned around a coffee table, while a wall-mounted television hangs above a modern fireplace. Soft blue carpeting adds warmth to the decor.

Home in Wrigleyville

4.91 out of 5 average rating, 186 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, DRAMATIC SPACIOUS Loft condo w/ PRIVATE ROOFTOP overlooking skyline! Open 2-story layout w/7 individual bed options, 3 full bathrooms, fully-stocked kitchen + huge island. Enjoy luxury flooring, soaring high ceilings, keyless entry, 2 HD TVs, & grill. Perfect for special occasions! Next to Wrigley bars & restaurants. Train to Downtown only 12 mins. Private parking spaces for rent. Awarded "GUEST FAVORITE" badge! Host carries over 1275 5-star reviews across listings!

Top guest favorite

A comfortable living area showcases a modern design with a large flat-screen TV mounted on a stone feature wall. Soft lighting highlights a cozy seating arrangement, including a plush sofa and two armchairs. A decorative coffee table sits in the center, contributing to a welcoming atmosphere.

Apartment in Albany Park

4.97 out of 5 average rating, 162 reviews

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

5-BD, 2-BR duplex; a combination of first floor and garden units. Just a 3-minute walk from the train, our property is the perfect place for your big gathering. Sleeps up to 12 guests with indoor Jacuzzi, full kitchen, free indoor parking( 1 car), and private patio. Access to grill, fire pit 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 favorite

A spacious living area features large windows allowing ample natural light. Contemporary furniture is arranged for comfort, including a leather sectional, accent chairs, and a round ottoman. The open layout leads to a modern kitchen, creating an inviting and functional space for gatherings.

Apartment in Wicker Park

4.89 out of 5 average rating, 111 reviews

Luxury Designer Penthouse Loft | Sleeps 20

Designer Penthouse in the heart of Wicker Park! Sleeps up to 20 people! Enjoy your own private loft in Chicago's hip and trendy Wicker Park-one of the city's centers nightlife, restaurants and cultural scene. This 4,500 square foot penthouse sits on an entire floor features 18 foot open vaulted ceilings, authentic loft feel, 4 bedrooms/3 bathrooms, and is perfect for families, professionals visiting the city on work trips, and everything in between. The cityscape views are truly unbeatable!

Top guest favorite

A spacious living room features a large navy sofa adjacent to a modern coffee table on a textured rug. Colorful artwork adorns the walls, and a flat-screen TV is mounted for entertainment. Light streams through windows, enhancing the open, airy atmosphere.

Home in Lake View

4.89 out of 5 average rating, 187 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 favorite

A modern living area showcases a coffered ceiling and stylish furnishings. Plush sofas and accent chairs are arranged around a coffee table, with a large wall-mounted television and a decorative painting enhancing the aesthetic. Natural light enters through multiple windows, illuminating the space.

Condo in West Town

4.98 out of 5 average rating, 178 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.

Guest favorite

The living area features a stylish yellow sofa paired with two accent chairs. A round coffee table sits on a soft area rug, while large windows are dressed with sheer curtains, allowing natural light to fill the space. A decorative plant adds a touch of greenery.

Home in Avondale

4.84 out of 5 average rating, 132 reviews

The Logandale: HUGE Mid-Century Home, sleeps 15

Welcome to The Logandale! This 4 bed/3 bath mid-century modern home is ideal for families, professionals, and groups. Enjoy an open floor plan, private patio, game room, and bedrooms with memory foam mattresses. The fully-equipped kitchen, Smart TVs with Netflix, and a backyard fire pit ensure a comfortable stay. Located in the trendy Avondale/Logan Square, you're close to public transport, eateries, and attractions. Experience Chicago's best with us! 🌃🛏️🎮🔥

Superhost

A stylish living area features a comfortable gray sofa accompanied by decorative pillows. A modern coffee table sits atop a patterned area rug, with a floor lamp providing soft lighting. Natural light floods in through large windows, enhancing the inviting layout.

Condo in Lake View

4.83 out of 5 average rating, 102 reviews

Breathtaking Getaway In Prime Lakeview Location!

Prime location in Lakeview, steps from the Southport Corridor, only one mile from Wrigley! My fantastic four bedroom apartment is the perfect home base for any group of travelers staying in the magnificent Windy City. The best dining, shopping, and entertainment are abundant in this hot Chicago neighborhood, and downtown is just a train ride away. You'll love the gorgeous exposed brick walls throughout the home as well as the thoughtful design and furnishings.

Top guest favorite

A cozy living room features a warm fireplace with a flat-screen TV mounted above. Comfortable leather chairs and a plush sofa surround a coffee table, while large windows allow natural light to fill the space. Potted plants add a touch of greenery.

Bungalow in Lake View

4.95 out of 5 average rating, 131 reviews

Chicago Bootlegger House Sleeps 10-20

Walk to restaurants, groceries, shopping, Wrigley Field, Lake Michigan, Beaches, Boat Harbor, Lincoln Park Zoo, night life, bars, clubs, Red Line Train, Lakeshore Drive and more; all just a few blocks from your door. Giant house on 2 levels with over 3,500 square feet of living space and 6 bedrooms. Nicely decorated and lots of places to sit and mingle or watch one of the 85" TVs. Private 2 spot parking in garage and a parking pad for oversized vehicles.

Guest favorite

The living and dining area presents an open-concept design, featuring a large sectional sofa with decorative pillows, a glass coffee table, and a television. A dining table with ample seating is positioned near the large window, allowing natural light to illuminate the space.

Townhouse in Uptown

4.96 out of 5 average rating, 156 reviews

Ravenswood 4BR Rowhouse + Free Parking Included

• 4 bedrooms (3 queens, 3 twins, and 2 futons) • free private dedicated outdoor parking space • close to popular neighborhoods such as Wrigleyville (6 min drive), Andersonville, and Uptown • easy access to public trains (Metra, Red line Wilson and Brown line Montrose stops) and buses • 20 min to downtown Chicago by car • Easy access to Evanston by Metra (Ravenswood train stop) - 4 stops • Close to Montrose Beach • 94/100 walking score

Guest favorite

A modern living area features a gray sofa with orange accent cushions positioned in front of a low glass coffee table. Framed artwork adorns the white walls, complemented by a standing lamp and a potted plant. A patterned area rug adds warmth to the space.

Home in Logan Square

4.95 out of 5 average rating, 139 reviews

Modern, Fully Renovated Logan Square Coach House

Newly renovated and modern 4 br coach house designed to be your home away from home in Chicago! Comfortable furniture, clean decor, fresh linens / towels, Amazon Fire TV, and dining area allow for a great stay. You will be minutes away from some of the best restaurants and bars Chicago has to offer and only a 20 minute train ride from the Loop via CTA.

Top guest favorite

A modern living area is displayed, featuring a gray sofa with a yellow patterned pillow. A marble coffee table sits in front, accompanied by a comfortable armchair. A dining area with a table and chairs is visible, alongside a decorative green wall and framed photographs.

Condo in Wrigleyville

4.99 out of 5 average rating, 164 reviews

Luxury 4 bedroom steps from Wrigley

Luxury duplex-down just steps to Wrigley Field. Located in the heart of Wrigleyville and just steps from both the ballpark and the redline, this condo is perfectly located for a day at Wrigley or a night downtown. Great for families, corporate events, and big groups looking to experience all the city has to offer.