Vacation rentals with a fireplace in South Side

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Top-rated fireplace rentals in South Side

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Guest favorite

Rental unit in Berwyn

4.91 out of 5 average rating, 324 reviews

Private apartment with retro vibe

Gunderson Getaway is a cosy one BR apartment with some retro style touches in Berwyn a block from Oak Park. 2nd floor private apartment. Wifi, cable, premium channels. Full kitchen. Queen bed plus sofa & extra single bed available. EASY free street parking right by unit. Quick drive to City. Convenient to both airports, United Center and walk to Fitzgerald’s Club. Near Blue Line, restaurants, groceries, great bakery. NO smoking, candles or glitter! Pets MUST be pre-approved and never left alone.

Guest favorite

Guesthouse in Chicago

4.93 out of 5 average rating, 100 reviews

Modern Chicago Home Away from Home

Nestled in between trendy, up-and-coming Bridgeport and vibrant Chinatown with easy access to buses, trains, and highways, our 2-bedroom coach house puts Chicago within your grasp. Major hotspots like McCormick Place, Soldier Field, Museum Campus, Grant Park and the Loop are an easy Uber ride away. Chicago is a world-class city with so many things to do and see and hear and eat. It'll be impossible to do it all in a day, so let us help you recharge before you go out and do it all over again!

Guest favorite

Guest suite in Chicago

4.98 out of 5 average rating, 136 reviews

Gorgeous Studio 15 Minutes From Ohare!

Private, cozy and spacious studio apartment. This wonderful apartment is clean and ready to be your home away from home in Chicago! Full kitchen and bath! Spacious Backyard! Free Parking! On a beautiful treelined street in the Dunning neighborhood. Great for couples & business travelers! Close to great restaurants and parks, Rosemont Convention Center (10 minutes), O’ Hare Aiport (15 minutes), Downtown (35-45minutes). *Travel times are non rush hour and can increase depending on time/events*

Superhost

Guesthouse in Chicago

4.91 out of 5 average rating, 340 reviews

Private Studio in Bridgeport, Chicago

A bright studio guesthouse, perfect for business travelers, a couple’s getaway, personal retreat, or a solo adventurer. Has a kitchen sink, cabinet space for your non-perishable items, a microwave, mini-fridge, and Keurig. We provide plates, flatware, mugs, and glasses. The studio offers the privacy of your own bathroom and shower facilities. You'll rest well in a full-size Murphy bed, with sufficient storage for all your travel items. A couch is available for a third guest if needed.

Guest favorite

Condo in Chicago

4.86 out of 5 average rating, 139 reviews

Quiet, Modern, Convenient 2 bedroom condo

PLEASE READ DESCRIPTION PRIOR TO BOOKING* Stay at this quiet, charming, Chicago-themed garden unit suite, sitting in the heart of Chicago's historic Bronzeville neighborhood. This convenient location with 1000 sq feet of space is perfect for young professionals, student, small groups, families, and people traveling with children. Easy access to public transportation, downtown Chicago, the Museum of Science and Industry, the University of Chicago, downtown Hyde Park, and so much more.

Superhost

Rental unit in Chicago

4.82 out of 5 average rating, 166 reviews

University Retreat

Lovely 3 bedroom apartment in Hyde Park location. Within one block of the U of Chicago; close to the science museum, Metra, restaurants, parks, and less than 1 mile from the proposed Obama Library and the lake. Updated unit has nearly 1,300 SF of livable space to enjoy: vintage hardwood floors throughout, separate living/dining rooms, kitchen with new stainless steel appliances, new furnace, new hot water tank, and a new porch with large fenced yard. Permit parking for guests only!

Guest favorite

Home in Chicago

4.98 out of 5 average rating, 345 reviews

Cozy garden apartment historic Jackson Bvld.

Just a short walk to the United Center our cozy 1 bdrm garden apt is located on Historic Jackson Blvd's tree lined st. Stop back & warm up by the fireplace before heading out to near by shopping & restaurants. Less than an hour from Midway or O'Hare. Walking distance to Randolph St. Restaurant Row, Little Italy, Greek Town, Union Pk, Fulton Warehouse Dist, Rush Hospital and UIC. A quick train/bus to The Loop, Theater Dist, Mag Mile, Wicker Pk. Free, convenient street pkg.

Guest favorite

Rental unit in Chicago

4.96 out of 5 average rating, 521 reviews

Stunning Retro Apartment in Andersonville

Stay in this perfectly situated apartment in the heart of vibrant Andersonville and find out why TimeOut Magazine calls this “The Coolest Neighborhood in the US”. Full of natural light, this 2 bedroom, 1 bath home has generous room sizes, and located on the ground floor of an immaculately kept vintage 4 unit building that has been fully upgraded with modern amenities. Plenty of free parking 24/7. Folks who stay here really will get an authentic Chicago-style experience.

Guest favorite

Loft in Chicago

4.94 out of 5 average rating, 171 reviews

Entire Spacious, Private Loft Apt Historic Beverly

You have the loft suite to yourself. Best for 1 - 2 people Access through the front door & complete privacy with a bathroom and separate entrance (locked doors) in a victorian farmhouse in lovely, tree-lined historic Beverly. Cozy, safe & well stocked with beverages & snacks. We are onsite hosts as we live on the 1st two floors. NOT SUITABLE if you have difficulty with stairs or lots of luggage (3rd floor) Queen bed & two twin beds avail Free street parking

Guest favorite

Home in Lansing

4.8 out of 5 average rating, 100 reviews

Holiday Season at The Walter Experience

*Complimentary Early Check in( Depending on availability). Located 35 mins from Downtown Chicago. Perfect lodging with a cozy home feel! Ideal for a Business Traveler or Corporate Rental(Easy Access to I 90/94). -A Couple or a Single Person seeking a private uninterrupted relaxing accommodation. Tour our town or neighboring towns ( indiana state line 2 mins away-Munster/Hammond/ Schererville -Lower taxes,Gas,etc. Local entertainment (shows or other events)

Guest favorite

Rental unit in Chicago

4.86 out of 5 average rating, 292 reviews

Charming loft style suite

Original loft style 2nd floor apartment with private entrance. Thoughtfully furnished two bedrooms with a queen bed in each room. Plus a build in king size tatami in family room. A eat-in kitchen is convenient for basic warm up/cooking. There is a mini fridge, coffee maker and microwave. 10-20 Minutes drive to Loop, Museum Campus, Mc Cormick Place, Illinois Medical District, Soldier Field, White Sox& United Center.

Guest favorite

Rental unit in Chicago

4.96 out of 5 average rating, 142 reviews

Sprawling South Loop 3Br/2Ba with parking

Conveniently located near McCormick Place and Soldier Field. Close to parks, shopping, and public transportation. Newly remodeled unit. Second floor unit with no elevator in building. Modern bathrooms and kitchen, new fixtures throughout, nice front deck, in-unit full-sized washer and dryer, hardwood floors throughout. One parking space included, but absolutely NO OVERSIZED VEHICLES