Family-friendly holiday rentals in Edgewater

Edgewater escape, charming 2 BR, Rooftop Solar

Self check-in to a charming 2-BR+ liv/dining room, private entrance garden apartment, 3 blks to Red Line or Metra to downtown or Evanston, Skokie, theaters, restaurants, and parks. Edgewater has tree-lined streets, known as a quiet, safe, diverse & friendly neighborhood. Breakfast foods (coffee, tea, fruit, milk, cereal, bread, homemade jam) for starters. Has a microwave, small fridge, toaster oven & induction stovetop. Your stay reduces carbon emissions due to solar panels & heat/ac pumps.

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.

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.

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.

Andersonville's Secret Garden: 2 beds, 1 bath

This serene retreat is tucked away amongst the tree-lined streets of the Lakewood Balmoral historic district. Guests can venture just two blocks to dive into the hustle and bustle of Andersonville, with its incredible food scene and unique local shopping spots. Those looking to explore all that Chicago has to offer will enjoy easy access to the CTA redline, major bus routes, and Divvy stations (our shared bike provider).

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.

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.