Family-friendly holiday rentals in Edgewater

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.

Newly Renovated, Spacious 2BR in Andersonville

Welcome to your newly renovated 2nd floor oasis! Located on a serene residential street, with a private parking space and backyard, this cozy retreat is nestled between the vibrant Edgewater and Andersonville neighborhoods. Indulge in a plethora of dining and entertainment options just steps away, or take a 15-minute stroll to the CTA Redline for easy access to downtown. With a new Metra stop at the end of the block and less than 10 miles from the heart of the city, your urban adventure awaits!

Edgewater, private, charming coach house 1 (of 2) Licensed by the City of Chicago 2209375

Our Edgewater coach house is a haven in the city. A ten minute walk to Hollywood Beach, a fifteen minute walk to fun Andersonville and a five minute walk to the 'L' train for direct downtown access, it is near to everything but feels far away from the busy city. Great restaurants are right around the corner, and Wholefoods is three blocks away. Managed 100% for guests, two independent units are superbly comfortable/ pristine. All essentials and more provided. Enjoy the city and relax at once.

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.

lakefront apartment

This is located steps away from Ardmore Avenue Beach on Sheridan Rd (chicago city street noise), with it's running and biking trails seen from apartment. Less than 5 min walk to bus and train stops - easy access to a variety of areas and attractions, including the Magnificent Mile and the John Hancock Center. Also a few blocks away from Loyola University (beautiful serene view points of the lake). The apartment is cozy with intentional design touches that will make you feel right at home.

Bright Colorful Boho-Chic Studio in Lincoln Square

Kick back & relax in your home away from home in our modern & peaceful studio space with 15-foot ceilings in the heart of the Lincoln Square neighborhood. Featuring natural light, modern amenities & beautiful artwork, the house is impeccably clean and designed to ensure you have the best travel experience possible. Located on the popular Foster Ave close to Winnemac Park, you're only blocks away from bakeries, farm-to-table restaurants, independent coffee shops and local breweries.

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.

Steps from the Lake, Lovely 3-Bedroom Condo

Enjoy all that Chicago has to offer in this beautiful Edgewater home. Lakefront beaches are steps away, as is the red-line Granville stop. This condo is walking distance to the Loyola campus, many restaurants, grocery stores, gyms, antique stores, and more! There is ample street parking on Lakewood, often there is a space right outside the house. We provide daily parking passes for you to use during your stay.

Urban Garden Retreat, Chic Andersonville Getaway

Fully renovated 2-bedroom, 1-bath garden level apartment just steps away from all the amazing restaurants and shops in the Andersonville neighborhood. 95 Walk Score (Very Walkable) 72 Transit Score (Excellent Transit) 75 Bike Score (Very Bikeable with a Divvy bike rental 0.2 miles away) 0.7 miles to the lake 0.8 miles to Little Vietnam 1.1 miles to Loyola University 2.5 miles to Wrigley Field

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 Garden Living

This is an amazing garden level apartment right off Clark st. with all the shops and restaurants right down the block. Grab a coffee at the Coffee Studio or a drink at Little Bad Wolf . This unit has a brand new kitchen and has a Smart TV with Netflix and a huge living room to hang out, and new bathroom with a large shower. It also has a private bedroom and access to laundry.