Holiday rentals in Andersonville

Unbeatable location in Andersonville - Quiet 3-BR

Unbeatable location--just steps away from Andersonville's famous Clark Street! Enjoy the quiet, spacious 1st floor of our classic Chicago 2-flat building with modern touches and free street parking. We live upstairs, maintain the unit ourselves, and are glad to answer questions. You can easily spend your whole stay in Andersonville or explore our iconic city via quick Uber rides or public transportation. ***New sofa in living room and we recently painted the bedrooms. New photos coming soon!***

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!

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.

Lovely Apartment on Quaint Block in Andersonville

This private 1-bedroom garden apartment is located on a historical residential block in lovely Andersonville (Lakewood Balmoral) neighborhood. The apartment has one private bedroom with a queen bed, a living room with a door and nice queen sized sleeper-sofa, a kitchen/breakfast area and a bathroom. Located close to the heart of Andersonville/Clark Street, the area provides a fantastic variety restaurants & stores, 15 min walk to the lakefront, and plenty of transportation options.

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.

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!

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 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.

Private, Charming, Coach House Loft in Andersonville

After a day exploring the city, cook dinner in an open-plan kitchen with dark hardwood surfaces. Gather around an enduring wood table and unwind in the Midwestern aura of this apartment featuring robust wood floors and rustic-industrial decor.