Vacation rentals with a washer and dryer in Andersonville

A gated entryway is visible, featuring a wooden fence painted in a neutral tone. The gate is partially open, leading into a green space lined with trees and plants. The house entrance is seen in the background, with a clear sky above.

4.93 out of 5 average rating, 451 reviews

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.

4.99 out of 5 average rating, 102 reviews

A cozy living space features a vibrant orange sofa complemented by decorative throw pillows. A dining area with a small table stands beside a fully equipped kitchen. Artwork adorns the walls, while natural light streams through windows, enhancing the inviting atmosphere.

Condo in Lake View

Chic & Comfy • Close to Wrigley

Welcome to your comfy, cozy, cheerful hideaway in the beautiful Buena Park!☀️ Buena Park is a little-known gem. Our home is just blocks from the lakefront (4 blocks), Wrigley (6 blocks), and the major L-line in Chicago (1 block)...yet, you'd never know it given how peaceful and serene it is! We live here part-time, so rest assured you'll have everything you need for a comfortable and enjoyable stay. We ask you please respect our place, and that you enjoy the trinkets + personal items we have!

Superhost

An inviting living area features a spacious gray couch adorned with blue and white cushions. A modern coffee table with a decorative tray sits on polished hardwood floors, while large windows allow natural light to fill the space, providing views of the surrounding greenery.

Condo in Uptown

4.86 out of 5 average rating, 222 reviews

The Bright Retreat in Andersonville

Stay in the heart of Andersonville when you book this bright, newly renovated condo. The home is one block from Clark Street near some of Chicago's best restaurants. It is 3 blocks from the Argyle Red Line stop, which will get you to Wrigley in 15 minutes and downtown in 30 minutes. The home includes a fully stocked kitchen, free parking spot (small and medium size cars and SUVs only, not large vehicles), in unit washer & dryer, queen-size bed, and couch with queen-size memory foam mattress.

Apartment in Andersonville

A red brick three-flat building is presented with large windows and intricate architectural details. Colorful pumpkins are arranged in the front garden, which features lush greenery and blooming flowers. A rainbow flag is displayed prominently by the entrance, adding a touch of vibrant color.

5 out of 5 average rating, 121 reviews

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.

A modern kitchen showcases sleek white cabinetry and a large island with seating for three on black stools. Open shelving displays various glassware. A stainless steel range hood is positioned above the gas cooktop, while natural light fills the space through windows.

4.99 out of 5 average rating, 146 reviews

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!

Apartment in Andersonville

A modern living room features a large white leather sectional sofa positioned near a wall-mounted television. A sleek electric fireplace is located beneath the TV. Bright overhead lights illuminate the space, while potted plants and windows add natural accents.

4.97 out of 5 average rating, 127 reviews

Quiet city getaway by beach in fun neighborhood

Welcome to this bright and modern 2 bedroom 1 bath getaway, 1.5 blocks to Andersonville + Uptown shops and dining. Located on a quiet tree-lined street walking distance to Foster beach, grocery, concerts, and CTA for easy access downtown. Two bikes provided to explore Chicago’s neighborhoods and beautiful lakefront path. Additional amenities include beach towels, volleyball, cooler, free on-site w/d and parking. Comfortably sleeps 4 and can accommodate 6 with air mattress. Key code entry.

A charming exterior view of the coach house is framed by lush greenery. Vibrant vines climb the side of the building, while two birch trees stand gracefully, adding a natural touch. Large windows illuminate the interior, inviting guests into a serene environment.

4.89 out of 5 average rating, 123 reviews

Edgewater, private, charming coach house 2 (of 2) Licensed by the City of Chicago 2209376

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.

A cozy living room is presented with a soft area rug and a contemporary ceiling fan. Two armchairs in vibrant colors face a stylish sofa adorned with decorative pillows. A coffee table sits in the center, while a large mirror and art piece add visual interest to the space.

4.97 out of 5 average rating, 107 reviews

Bright 2BR Andersonville – Walk to Lake & Dining

Steps to Chicago’s lakefront, dining, and summer festivals — your bright Andersonville retreat awaits! Wake up to tree-lined streets, stroll to cozy cafes and local boutiques, or spend the afternoon exploring Lake Michigan’s shores. This stylish 2BR flat blends vintage charm with modern comforts—ideal for couples, remote workers, and weekend explorers. Enjoy Superhost hospitality, fast Wi-Fi, and a fully stocked kitchen for a stay that feels like home. We can't wait to welcome you soon!

Apartment in Andersonville

The bright living area features a grey sofa adorned with colorful cushions. Two teal chairs are positioned nearby, adding a pop of color. Natural light floods the space through oversized windows, highlighting the vibrant artwork on the wall and a modern coffee table at the center.

4.95 out of 5 average rating, 574 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.

Apartment in Lincoln Square

A light-filled living area features large windows with green curtains and a view of the courtyard. A comfortable sofa with decorative cushions is positioned next to a wooden coffee table, which holds a book and a small plant. A TV is set on a stylish console.

4.86 out of 5 average rating, 374 reviews

Renovated Designer Flat in Heart of Lincoln Square

Kick back with a fresh coffee and enjoy the designer touches of this renovated apartment, including marble worktops, wood floors and 1920s exposed brickwork. There are great courtyard views, while the memory foam mattress and super-sized sofa add real comfort. Lincoln Square is a quaint, family-friendly neighborhood. There's abundant German influence here, and great shops, restaurants, and bars line Lincoln Avenue. Downtown is 20 mins by train. Wrigley Field is close too.

4.92 out of 5 average rating, 184 reviews

A spacious living area is centered around a glass-top coffee table, surrounded by stylish seating options in soft hues. A wall-mounted television is visible along with a dining table set for four. Natural light filters through large windows, enhancing the inviting ambiance.

Condo in Andersonville

Warm & Comforting 4br/2ba In Andersonville

Our 4BR/2BA home offers the perfect balance of quiet and convenience. Step out the front door into the tree-lined streets and walk just minutes to the heart of Andersonville for some exciting and historic neighborhood culture or to the Red Line which grants access to everything the City has to offer! Whether you are in town as a tourist, visiting friends, or on business, you will feel right at home!