Family-friendly holiday rentals in Andersonville

Ravenswood Guest House Annex

The Annex is a private apartment in an 100+ year old wood frame home just north of Andersonville. The Annex is a typical Chicago style 'in-law' garden apartment - located on the first floor of the house where we live - it is bright and clean and well appointed with comfortable furniture. (see pictures). It has large windows that look out on our garden and yard. Our daughter's family also lives on the property in rear coach house. There is easy access to Lake Shore Drive, Evanston and downtown.

Andersonville 2 bed with modern kitchen + bath

Hi, we're Mike and Lora. Our beautiful Mission-style three-flat is located about 100 ft. from Clark St. in Andersonville, with great bars, restaurants, and shopping just outside our door. Half a mile east is the Red Line, which gets you right downtown, and just past that is beautiful Foster Beach. We live upstairs and are happy to offer recommendations. We love it here! The apartment was rehabbed in 2019 and features a large kitchen with tons of counter space, in-unit laundry, and queen beds.

Gorgeous, cozy 1-bedroom Suite in Andersonville

Our place is a short walking distance to everything. “Timeout” rated Andersonville #2 of the “worlds coolest neighborhoods”. Check out their Neighborhood Guide online for the best restaurants, bars & shops to visit. You’ll love your suite because of the quiet ambiance, location, complete privacy and NO cleaning fee. We are close to public transport and about 1 mile to the lakefront & Lake Shore Drive. 5 miles N of downtown Chicago. Perfect for couples, solo adventurers and business travelers.

1-Bedroom Apt by Andersonville & Lakefront

Spacious, sunny 1-bedroom apartment in peaceful, historic Edgewater neighborhood of Chicago. Overlooks park and is short walk from Thorndale Red Line "L" station, the beach, Whole Foods, and shops, restaurants, and bars in Andersonville. Ideal for up to 4 people, has queen-size bed in bedroom and sleeper sofa in living room. Kitchen is fully equipped with gas stove, microwave, fridge, coffee machine, and utensils. Free high-speed WiFi. Smart TV. Clean and comfortable with modern touches.

Private Andersonville Apartment

Enjoy your stay in this private 3-bedroom upper apartment with separate entrances and free street parking available. Three separate bedrooms offer total comfortable sleeping for up to 6. Full eat-in kitchen, comfortable living room, and work space make it easy to work or relax here while enjoying all that Chicago and Andersonville have to offer! Fast WiFi is included along with a nice workspace. The apartment is close to Clark Street and a short walk to CTA bus and Red Line.

Edgewater Studio on Paulina

Our garden unit is nestled in the charming Edgewater neighborhood of Chicago, just a short walking distance from the vibrant Andersonville area where you will find several shopping and dining options. Situated in a convenient location, our unit offers easy access to public transit options including bus routes and Red Line as well as permitted street parking. We look forward to hosting, where comfort, convenience, and the best of Chicago's neighborhoods await you.

Cozy and Private Andersonville Retro Studio

In the heart of Andersonville, this cozy, vintage-inspired studio apartment can be your home away from home. Located on the garden level, it is only 2 steps down to your own private oasis in the city. Separate private building entrance and no shared spaces in the entire basement suite. Sparkling clean and every detail considered for your comfort. Enjoy living like a local steps from Chicago's best 'hood, while experiencing the comforts of home.

Stylish 2BR Andersonville — Walk to Lake & Cafés

Steps to Chicago’s lakefront, cozy cafes, and Andersonville’s best shops. This bright 2BR blends vintage charm with fast Wi-Fi, plush bedding, and a fully stocked kitchen—ideal for couples, remote workers, and weekend explorers. Stroll tree-lined streets, explore the nearby lakefront, or curl up indoors as the seasons change. Enjoy Superhost hospitality for an effortless stay. We’d love to host your next Chicago escape.

Cozy Andersonville Cabin

Our cabin-in-the-city is a relaxing garden apartment, located in the popular LGBTQ+ friendly Andersonville area of Chicago. The cabin unit is decorated in bear and nature themes, with warm and cozy pine walls - like you were renting a cabin in the woods! Our place is a half a block from the main strip. Plenty of great shopping, award winning dining, and fun night life is just steps from our house!

Vibrant & Chic Apt On Quiet St in Andersonville

Welcome to this thoughtfully remodeled 1925’s two-flat building located in the Second Coolest Neighborhood in the US. While this stylish space is the perfect relaxing stay, its location makes it easy for you to get around. *Free street parking You are only: 5 min walk to Clark St & Exceptional restaurants & bars 6 min drive to Lakefront & Lakeshore Drive... 17 min drive to Downtown Chicago...

Andersonville Bicycle Studio

Enjoy a stylish experience at this centrally-located Andersonville studio. The Bicycle Studio leaves no detail untouched - modern amenities with the charm of exposed brick and timber beams. You are two blocks away from Chicago's popular Andersonville neighborhood - endless dining, shopping and entertainment. Quick access to public transportation and Chicago's lakefront.

Andersonville Living

Sunny 3 Bedroom 1 Bath located in Andersonville right off Clark St. with its shopping, bars and restaurants. The apartment has vintage charm with original woodwork and floors as well as modern amenities such as the new kitchen and central AC. There is a large sunny back deck for sipping your morning coffee, wifi, cable and Amazon for your media needs.