Holiday rentals in Edgewater, Chicago

4.92 out of 5 average rating, 432 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.

4.89 out of 5 average rating, 92 reviews

Adorable Private Edgewater Suite

Cozy exposed brick, garden unit on a quiet street, perfect for relaxing after a night out in the city! Comfy, queen-sized bed, full kitchenette and gated private side entrance so its the perfect spot for your trip to Chicago! We are right by the exciting nightlife of Andersonville and a 10 minute walk to the beach/start of the Lakefront trail. Public Transit is close and easily accessible, the redline "L" can get you downtown in a half-hour train ride. Close to Loyola University, Go Ramblers!

4.96 out of 5 average rating, 140 reviews

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.

Guest suite in Andersonville

4.96 out of 5 average rating, 373 reviews

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.

Superhost

4.81 out of 5 average rating, 154 reviews

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.

4.98 out of 5 average rating, 243 reviews

Foster Flat - Retreat to your Home Away from Home

The perfect place to stay for your next trip to Chicago. This fully furnished 2 bedroom/1 bath unit features bright living spaces with modern decor. Located just a few blocks from the heart of Andersonville, you'll find coffee shops, restaurants, shopping and nightlife. Lincoln Square and Ravenswood neighborhoods are also nearby for you to explore. Conveniently located to public transportation (buses, Red and Brown Line trains, as well as Metra), you'll have no trouble getting around town.

4.97 out of 5 average rating, 87 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!

5 out of 5 average rating, 132 reviews

Flat in East Rogers Park

Remodeled, Near Loyola, Beach and Subway

Stylish and sophisticated, this remodeled 3 bedroom, 2 bath private apartment is in a prime location, 3 blocks from Hartigan Beach, and 2 blocks to the Loyola Red Line "L" station to take you to Wrigley Field, downtown & many locations in between. We are 2 blocks from Loyola University & about 4 miles to Northwestern University. Located on a quiet, residential tree-lined street, we are a 2 block walk from all manner of restaurants & conveniences associated with our proximity to Loyola.

4.95 out of 5 average rating, 556 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 East Rogers Park

4.93 out of 5 average rating, 240 reviews

Cozy 1bdr Rogers Park, Loyola, Northwestern.

Visiting Northwestern, Loyola University, Rogers Park or Evanston? This cozy AirBnb is perfectly situated. A beautifully clean, private apartment 2 blocks from parks & sand beaches, walking distance to Loyola, short ride to Northwestern, steps to public transportation & restaurants, red line "El" trains & bus routes. Apt has private, queen bedroom, en suite full bathroom, living room w/queen sofa bed,TV, dining table, & partial kitchenette. Note: no full kitchen.

4.95 out of 5 average rating, 65 reviews

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 street parking. We look forward to hosting, where comfort, convenience, and the best of Chicago's neighborhoods await you.

4.92 out of 5 average rating, 142 reviews

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).

Holiday rentals for every style

Get the amount of space that is right for you

Flats

Convenient locations with everyday essentials

Hotels

Stylish accommodation and amenities

Unique stays

Spaces that are more than just a place to sleep

Popular amenities for Edgewater, Chicago holiday rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great holiday rentals in Edgewater, Chicago

Private room in East Rogers Park

4.97 out of 5 average rating, 104 reviews

The Stained Glass Apt. Edgewater #2

DavidRating, 5 stars3 weeks ago

Felice was a wonderful host, engaging to the extent desired. She was easy to connect with and seems to enjoy her guest. The location is perfect for someone going to the Chicago Mosaic School and the Granville Red Station which means you can easily get downtown. I feel fortunate to have this gem. It is especially good for travelers who don’t plan to cook. Food establishments are readily available and appreciate your business. Thank you Felice for making my stay comfortable and welcoming.

5 out of 5 average rating, 6 reviews

2BR Apartment close to Stores

LauraRating, 5 stars1 week ago

Very comfortable bedding and pillows, like a five star hotel! This place is brand new, updated/modern and with all the windows it’s bright with natural light. Also very safe. Parking was always easy and ample. Location is surrounded by mainly single family homes, so it’s very quiet for being in the city. We walked to many restaurants including our favorite coffee/breakfast joint Collectivo. They have the BEST sausage/egg/cheese biscuits. We will definitely return!

5 out of 5 average rating, 132 reviews

Private room in Uptown

Easily accessible Uptown room

MarinaRating, 5 stars2 weeks ago

We absolutely loved starting at Cameron’s place! It was so clean, beautiful and in the perfect location for us. Cameron was so kind and helpful and really set the bar for what an Airbnb host should be. We would definitely book to stay there again!

Private room in Andersonville

4.95 out of 5 average rating, 262 reviews

Great Edgewater/Andersonville private suite

JacobRating, 5 stars1 week ago

Great location, great accomodations, and most importantly amazing hosts! Tripp and Todd were so welcoming, I felt right at home. They provided helpful suggestions for meals, activities, transport, etc. Hosts were in communication from the moment I landed to coordinate checkin, and allowed me to drop off my bags early when I arrived prior to the check in time. The location is great, only a few minutes walk to Clark Street which is well populated and has many restaurants and independent shops. Do yourself a favor and book with Tripp and Todd if you ever find yourself in Andersonville/Edgewater!

5 out of 5 average rating, 13 reviews

Home in Andersonville

Charming 3bd Bungalow In Vibrant Andersonville

CharlesRating, 5 stars1 week ago

Great home and location. Taranee’s place is clean and close to Andersonville’s Clark Street with tons of restaurants and shops. Parking was easy around the home. Great workspace for those who need that. Kitchen is updated and well stocked with cooking and serving items. Highly recommend.

4.91 out of 5 average rating, 91 reviews

Remodeled, Modern, Spacious 1- Bedroom Garden Apt

AshleyRating, 5 stars7 months ago

Loved this Airbnb - would gladly stay here again! Everything I needed was right there an an excellent area to walk my dog in! Felt right at home and Roberto is extremely kind and helpful! Very appreciated - highly recommend staying here!!!

Private room in Andersonville

4.98 out of 5 average rating, 321 reviews

Super Cozy Bed/Bath in Awesome Andersonville Home!

JackRating, 5 stars1 week ago

Marty and Rob’s place was perfect for our stay in Chicago. Located in the lovely neighbourhood of Andersonville, their home is well connected to anywhere that you might need to go in the city! The house is super clean and well stocked with everything that you might need, including some thoughtful touches like a couple of bottles of cold water on arrival. The bathroom is fully stocked and there are plenty of clean towels provided, and if you run out they are more than happy to wash them and give them back to you, which is handy! We would definitely stay with Marty and Rob again when we’re next in Chicago. Thanks so much!