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Mansion vacation rentals in Chicago

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Top-rated mansion rentals in Chicago

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Rental unit in Lake View

4.82 out of 5 average rating, 306 reviews

Sophisticated, Historic & Comfy Flat near Wrigley!

Down comforters, nice towels and linens + stylish design and comfort You will have access to the entire space - 4 bedrooms, 2 bathrooms, living room, dining room, kitchen, back deck, and back yard. Send me a text or call. This home is in the heart of it all, just a 10-minute drive to the lake, beach, and Wrigley Field. A strip mall is close by with different food outlets. Uptown's Green Mill Jazz club, Riviera Theatre, and Aragon Ballroom are a short bus ride away. The Montrose Brown Line stop is a 7 minute walk directly west. The #22 bus is a 2 minute walk away and takes you to Wrigleyville (south 10 mins) and Andersonville (North 10 mins) The #78 bus stops right outside and can take you Montrose Beach (east 10 mins) or to the Blue Line airport transfer (west about 25 minutes) Free Street parking on Montrose or Ashland is usually available. Deluxe California King Blowup Mattress available for living room. Very comfortable.

Townhouse in Old Town

4.84 out of 5 average rating, 161 reviews

Downtown Elegance ✨ Private Yard Parking

This unique space features designer kitchen, art by a local artist throughout, marble master bath and most importantly incredible location. Walk to everything Chicago has to offer- Downtown, Mag Mile; North ave beach, zoo and Lincoln park, restaurants, bars, boutiques, nightlife of Gold Coast and Old Town from this spacious house on a quiet neighborhood street in historic Old Town. 4 bedrooms, 4 baths, 2 private outdoor spaces, kitchen plus a bar, 1 car parking, washer, dryer. Pets are welcome!

Condo in West Town

4.94 out of 5 average rating, 136 reviews

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!

Home in Irving Park

4.89 out of 5 average rating, 105 reviews

Stunning 6 BR Home * Chicago * Centrally Located

Welcome to a newly built luxury 6 bedroom house in Chicago’s family friendly Albany park neighborhood. Centrally located - close to downtown (25 min), Wrigley Field (15 min) and O'Hare (15 min) Large common areas and a chefs kitchen with a 5 person island allows large parties and families to stay comfortably. The house offers spacious rooms and a full laundry room on the second level. The home also includes a 2 car garage and the convenience of not having to worry about parking in Chicago!

Rental unit in Lake View

4.92 out of 5 average rating, 213 reviews

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.

Townhouse in West Loop

4.99 out of 5 average rating, 232 reviews

Spacious 4-Level/4-Bedroom Townhouse in West Loop

Spacious Townhouse in Chicago's Hip Foodie Neighborhood: West Loop/Fulton Market. This is a Private, 4-Story Townhouse on a Tree-Lined Street just Steps from the Action...while still quiet enough for a good night's sleep. Walk to some of the Nation's Top Restaurants (near Restaurant Row), Clubs, Pubs, Groceries, Parks, Coffee Shops. Easy Train Transit to O'Hare, Navy Pier, Mag Mile, McCormick Place, etc...Terrace w/Skyline Views & Attached Garage Parking for 1 Regular-Sized Vehicle Included!

Loft in West Loop

4.83 out of 5 average rating, 107 reviews

Luxury Penthouse Loft | Heart of Fulton Market

NEW PENTHOUSE LOFT IN FULTON MARKET! Enjoy your own private luxury loft in Chicago's bustling Fulton Market-the city's center of main nightlife, restaurants and cultural scene. This 3,500 square foot penthouse features 12 foot open lofted ceilings, a dedicated elevator entrance, free onsite garage parking, 5 bedrooms/3 bathrooms, and is perfect for families traveling to Chicago, professionals visiting the city on work trips, and everything in between. The cityscape views are unbeatable!

Home in Wrigleyville

4.91 out of 5 average rating, 172 reviews

Soaring Dramatic Wrigley Loft w/ PRIVATE ROOFTOP

Say "WOW" in this top floor, IMMACULATE SPACIOUS with cozy FIREPLACE + ROOFTOP overlooking skyline! Open 2-story layout w/7 bed options, 3 bathrooms, private rooftop with skyline. Luxury flooring, soaring high ceilings, fully-stocked kitchen + huge island, keyless entry, 2 HD TVs, & outdoor grill. Perfect for SPECIAL OCCASIONS! Next to all Wrigley bars & restaurants. Train to Downtown <12 mins. Private parking for rent. As a "GUEST FAVORITE" we boast >1220 5-star reviews across listings!

Townhouse in Old Town

4.94 out of 5 average rating, 109 reviews

Old Town/Lincoln Park Luxury Home Garage & Rooftop

Old town luxurious townhouse with rooftop, patio and attached garage (with Level 2 electric car charger for any type of electric car). The extra wide floor plan allows for 4 large bedrooms and 2.5 bathrooms spread over 4 levels of living. One block away from Brown Line station and 4 blocks away from Red Line station and best of Lincoln Park shopping. 10 minutes walk to North Avenue Beach or Lincoln Park Zoo. 5 minute walk to Second City, Zanies and Old Town dining & nightlife.

Condo in West Town

5 out of 5 average rating, 137 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.

Home in Old Town

4.87 out of 5 average rating, 129 reviews

Huge Home *Prime Spot *Yard *Parking *Fireplace

Unique opportunity to rent an original Victorian home in historic Old Town. Only listing of its kind! Walk to almost everything Chicago has to offer- Downtown, Magnificent mile, restaurants, bars, boutiques, and nightlife; Lincoln Park and North ave beach from this three-level house. 5 bedrooms, 3.5 baths, 2 fully stocked kitchens, 2 car garage, back yard, pets welcome - what else can you possibly need? Space is expandable from a smaller family to a group of 22.

Home in Lincoln Park

4.84 out of 5 average rating, 157 reviews

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!

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Popular amenities for Chicago mansion rentals

Free parking on premises

Air conditioning

Mansion rentals with a pool

Rental unit in The Loop

4.85 out of 5 average rating, 13 reviews

DTown Penthouse - 4bd/4ba (+Parking + Gym + Pool)

Home in Glen Ellyn

4.94 out of 5 average rating, 18 reviews

Glen Ellyn Home

Home in Munster

5 out of 5 average rating, 8 reviews

Munster hide away

Rental unit in Magnificent Mile

5 out of 5 average rating, 11 reviews

Luxury Designer Penthouse Combo West | Gold Coast

Home in Lockport

New place to stay

Hidden GEM OASIS in Chicagoland

Home in Bloomingdale

4.94 out of 5 average rating, 35 reviews

Whole House with a Hot Tub!

Rental unit in The Loop

5 out of 5 average rating, 3 reviews

Downtown Penthouse 5bd VIEWS|Parking, Gym+Pool

Luxury mansion rentals

Home in Lake View

4.95 out of 5 average rating, 111 reviews

Entire house 1 City block from Wrigley Field!

Home in Downers Grove

4.87 out of 5 average rating, 31 reviews

Luxury Bliss: Opulent 5BR/3.5BA Delightful Escape

Home in Roscoe Village

4.94 out of 5 average rating, 254 reviews

Duplex Home RoscoeVillage/Wrigley Free St Parking

Townhouse in West Town

4.96 out of 5 average rating, 68 reviews

Beautiful Spacious RiverWest Townhome 4-Bed/4-Bath

Condo in Lake View

4.81 out of 5 average rating, 124 reviews

Spacious Home, Incredible Lakeview Location

Home in Logan Square

5 out of 5 average rating, 36 reviews

Lux LoganHouse w/garage, Sleeps 12, & rooftop deck

Condo in Wrigleyville

4.99 out of 5 average rating, 146 reviews

Luxury 4 bedroom steps from Wrigley

Townhouse in West Town

4.91 out of 5 average rating, 117 reviews

Upscale 4-Bedroom Townhouse w/Garage - LOCATION

Pet-friendly mansion rentals

Rental unit in Uptown

4.94 out of 5 average rating, 154 reviews

❤️ Lowest Rates! Spacious Duplex with Parking!

Rental unit in Humboldt Park

4.92 out of 5 average rating, 100 reviews

Traditional Greystone Chicago 4-bedroom Duplex Apt

Home in Chicago

4.95 out of 5 average rating, 76 reviews

Spacious Row Home next to Transit w Garage

Home in Logan Square

4.91 out of 5 average rating, 139 reviews

Southwestern Luxury El Motel Dos | Sleeps 12

Home in Logan Square

4.95 out of 5 average rating, 140 reviews

The Grand Kimball Lodge, Logan Square, Sleeps 14

Rental unit in Lake View

4.96 out of 5 average rating, 54 reviews

5 Bedroom Wrigleyville Experience right by stadium

Condo in Westmont

4.78 out of 5 average rating, 60 reviews

bright two-story condo

Townhouse in Uptown

4.96 out of 5 average rating, 140 reviews

*SPACIOUS 4 Bedroom Townhouse with FREE PARKING!*

Destinations to explore