Vacation rentals in Kathy Osterman Beach

4.92 out of 5 average rating, 433 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, 365 reviews

A well-kept garden features blooming white hydrangeas surrounded by lush greenery. In the background, a classic two-story house displays a spacious balcony and a pergola, providing a serene outdoor dining area. The peaceful setting is complemented by seating among the vibrant plants.

Guest suite in Chicago

Private Lincoln Square one bed+bath studio apt.

Clean, bright studio apartment in Lincoln Square. Private entrance, queen bed, private bath and small kitchenette in one of Chicago's premier neighborhoods. (Small twin futon also available if needed.) Beautiful home and garden with plenty of free street parking. Easy walk to public transportation, incredible restaurants, music venues, and shopping. The lake, Wrigley Field and more are readily accessible by public transportation. Enjoy all of Chicago! Chicago Registration Number: R18000036336

A tranquil garden space features an inviting path paved with bricks, bordered by vibrant flower boxes filled with a variety of blooms. A rustic staircase leads to a charming coach house, while lush greenery and trees provide a serene atmosphere throughout the area.

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.

Superhost

A modern kitchen area features black cabinets and a granite countertop. Kitchen appliances, including a stove and an oven, are neatly aligned. A wooden dish rack sits by the sink, while natural light highlights the space. The adjoining living area is partially visible in the background.

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.

The exterior of a modern brick building is captured, showcasing a combination of dark brick and natural stone elements. Large windows allow natural light to fill the interior. A clean sidewalk leads to the entrance, framed by greenery and pebbled landscaping.

4.97 out of 5 average rating, 96 reviews

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.

The entrance features a warm wooden door adorned with a small circular mirror, welcoming guests into the space. A textured mat lies on the polished hardwood floor, leading to the softly lit hallway with light-colored walls.

4.95 out of 5 average rating, 557 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.

4.93 out of 5 average rating, 241 reviews

A sandy beach scene is captured with gentle waves lapping at the shore and people enjoying the water. In the foreground, a couple stands together, gazing out at the sea. Large, fluffy clouds drift above, adding to the serene atmosphere.

Condo in Chicago

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.

Three brown bottles with pump dispensers are mounted on a black wall bracket. The labels specify body wash, shampoo, and conditioner, all featuring a minimalist design. The background consists of textured grey tiles, contributing to a modern bathroom aesthetic.

4.95 out of 5 average rating, 66 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.

A well-organized workspace is displayed, featuring a wooden container filled with yellow pencils. Next to it, a glass terrarium with green leaves and small pebbles adds a touch of nature. A wooden sign with the phrase 'GOOD VIBES' is positioned prominently.

4.83 out of 5 average rating, 509 reviews

Lovely Chicago Apt | Hip Location w/ Top Food

Large 1 bedroom with all the essentials and kitchen for your stay in Chicago's entertainment district. Steps away from all the amazing restaurants and shops in Andersonville, Uptown's Asia on Argyle (best Pho in the city!), and a number of music venues (Aragon, Riveria, and The Green Mill). You'll also be a short walk from Foster Beach and Chicago's Lakefront Trail, beautiful parks, and public transportation (CTA Red Line, Buses, and Metra train).

4.97 out of 5 average rating, 120 reviews

A foosball table is positioned in the foreground, featuring uniform rows of players. The players are crafted from black with gold accents, arranged to create a competitive atmosphere. Bright light filters in from a nearby doorway, illuminating the game area.

Guest suite in Chicago

Modern Garden Apartment in Lincoln Square

Welcome to our stylish and updated one-bedroom apartment located in a classic brick building in Lincoln Square. Perfect for solo travelers or couples, the space features a comfortable queen bed and a bright, modern interior. Just a short walk to the Brown Line and steps from Lincoln Square’s cozy shops, top-rated restaurants, and vibrant local culture. Wrigley Field, downtown attractions, and Lske Michigan are easily accessible by bike or train.

A vibrant street scene features a mix of historic and modern buildings, showcasing various storefronts. Vehicles pass by on the road, while clear blue skies create a bright atmosphere. Notable signage indicates the presence of restaurants and shops, contributing to the neighborhood's lively character.

4.99 out of 5 average rating, 155 reviews

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...

A clean and functional kitchen area features a large white refrigerator alongside a matching stove. Countertops are adorned with white canisters for storage. Natural light illuminates the space, enhancing the organized layout and modern appliances.

4.98 out of 5 average rating, 198 reviews

Beautiful Hollywood-Ridge Suite in Edgewater

Beautiful, complete, and private apartment/suite in a historic Chicago Greystone located in the beautiful and diverse Edgewater neighborhood. Sleeps 1-4 persons (Queen bed in master bedroom and Deluxe Memory-Foam Queen Size Sofa Sleeper in living area). Suite features guest-controlled central air and heat, 2 flat screen TVs, private bath and shower, and full access to all rooms.

Vacation rentals for every style

Get the amount of space that is right for you

Hotels

Stylish accommodations and amenities

Unique stays

Spaces that are more than just a place to sleep

Homes

Comfortable places with all the essentials

Popular amenities for Kathy Osterman Beach vacation rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Other great vacation rentals in Kathy Osterman Beach

4.96 out of 5 average rating, 190 reviews

A well-maintained hospital exterior is featured, showcasing a clear sign directing to the Emergency entrance. Brightly colored flowers line the pathway, complemented by manicured greenery and trees. The modern brick building stands against a clear blue sky, indicating a welcoming and accessible environment.

Private room in Evanston

Welcoming Evanston Home

JoshuaRating, 5 stars2 weeks ago

Jennifer was a very hospitable host and I had a very pleasant stay. The room was very clean and quiet!

A spacious living area features hardwood flooring and large windows that allow natural light to fill the room. Comfortable seating options include a blue recliner and patterned armchairs, accented by plants and decorative elements. A coffee table sits centrally, enhancing an inviting environment.

4.99 out of 5 average rating, 153 reviews

At the junction of comfort and care

KristinaRating, 5 stars4 weeks ago

William is an amazing host who is very accommodating and helpful with all questions relating to parking and transit to downtown Chicago. He was very responsive to all my communications and was clear on expectations. Fantastic person and place!

An inviting living room is featured with two black leather sofas positioned around a central area rug in vibrant hues. A brick fireplace sits at the end of the room, flanked by built-in bookshelves displaying books and decorative items. Warm light filters through the windows.

4.97 out of 5 average rating, 105 reviews

The Stained Glass Apt. Edgewater #2

SandraRating, 5 stars5 days ago

I loved Felice’s home. It is decorated with great taste and artistry. The house is quiet, all the spaces are uniquely decorated, the kitchen is a wonderful work of craftsmanship, and although my room was small, it is very comfortable. I slept well. The area is very walkable and pretty, with lots of lined trees on the neighborhood streets. It is close to neighborhood shops and walking distance to the lake. Felice is a wonderful host. She is accesible and very friendly. She made me feel right at home.

A narrow hallway is shown, featuring warm-toned walls and wooden floors. Light fixtures are mounted on the walls, illuminating the path leading towards an open kitchen at the far end. Several doors line the sides, and a small table is positioned against the wall.

5 out of 5 average rating, 132 reviews

Easily accessible Uptown room

MarinaRating, 5 stars3 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!

4.91 out of 5 average rating, 104 reviews

An aerial view showcases the winding Lakeshore Drive alongside Lake Michigan. Lush greenery lines the waterfront path, with boats gently cruising on the water. The Chicago skyline rises in the background, characterized by various distinctive buildings against a clear blue sky.

Private room in Evanston

Room Mins to Downtown Chicago & Northwestern!

NataliaRating, 5 stars1 week ago

Musa was very friendly and helpful the entire time we stayed at his place. The house is big, neat and located in a nice and calm neighbourhood, ideal if you want to rest after a day in downtown. Good shops nearby so I recommend go for a walk around the beautiful Evanston.

A living area features a black leather sofa adorned with orange accent pillows. A wooden coffee table displays decorative items and candles. Large windows allow natural light to fill the space, surrounded by lush green plants and a striking wall art piece of a face.

4.95 out of 5 average rating, 262 reviews

Great Edgewater/Andersonville private suite

JacobRating, 5 stars2 weeks 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!

A cozy outdoor seating area features a woven loveseat with plush cushions, inviting relaxation. A matching ottoman rests in front, complemented by a small round table made of natural wood. Lush greenery surrounds the space, enhancing the tranquil atmosphere of the garden.

4.98 out of 5 average rating, 321 reviews

Super Cozy Bed/Bath in Awesome Andersonville Home!

JackRating, 5 stars2 weeks 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!

An elegantly remodeled bathroom features a large jetted tub under a slanted ceiling, complemented by a rainfall showerhead. A round mirror reflects soft lighting, while white subway tiles create a clean aesthetic. A small sink with a sleek faucet is positioned beside a cabinet.