Vacation rentals in Kathy Osterman Beach

Find and book unique accommodations on Airbnb

Top-rated vacation rentals in Kathy Osterman Beach

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Top guest favorite

A modern kitchen and living area are showcased within an open-concept space. The kitchen features stainless steel appliances and a large island with seating for three. The cozy living area includes comfortable seating and a low wooden coffee table, complemented by warm wooden flooring.

Apartment in Chicago

5 out of 5 average rating, 55 reviews

Brand New 1-BR Apt: Deluxe Comfort w/ Spa Bathroom

Why stay anywhere when you can experience luxury during your travels. This brand new 1-BR apartment was designed with a touch of elegance and offers amenities to make your experience not just satisfying, but memorable. At your finger tips is a full kitchen; luxury bathroom with enormous walk-in shower; separate bedroom w/ queen bed (extra day bed in living room to sleep 3 total); garage parking; garden access; cozy workspace; 2-Smart TVs; bicycle; ample storage for longer stays; WIFI; and more.

Top guest favorite

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.

Apartment in Chicago

5 out of 5 average rating, 122 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.

Top guest favorite

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.

Apartment in Chicago

4.99 out of 5 average rating, 147 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!

Guest favorite

The living room features hardwood flooring and is illuminated by natural light streaming through large bay windows. Two comfortable sofas face a coffee table, with a TV mounted on a console unit nearby. A warm and inviting atmosphere is created by the arrangement and decor.

Condo in Chicago

4.87 out of 5 average rating, 31 reviews

Comfy and Walkable

You will be close to everything when you stay at this comfortable apartment that is close to everything but quiet and friendly. This is my home. I travel a lot and airbnb it when I'm away. It's comfortable, safe, has all the things a lived-in home has, and is in an amazing location. It's like staying at your friend's apartment in the city. If you want luxury, pay more and stay somewhere else... but this is exactly the kind of place I'm looking for when I travel and I hope you'll enjoy it too!

Superhost

A cozy living area is showcased with a light-colored sofa adorned with throw pillows. A woven rug lies under a low coffee table, which holds small decor items. A potted plant adds a touch of greenery, and large windows allow natural light to fill the space.

Apartment in Chicago

4.8 out of 5 average rating, 162 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.

A spacious studio layout includes a comfortable futon and a cozy bed with a floral patterned coverlet. A small coffee table is positioned on a light area rug, while a dining table and kitchen area are visible in the background, highlighting a modern design.

Apartment in Chicago

4.76 out of 5 average rating, 25 reviews

Charming Studio 3blks to Beach

Homey studio in Chicago's historic Edgewater a few blocks from Lakefront beach amenities (weather-permitting) and Whole Foods for groceries. Easy access to public CTA and Redline trains (a block away), with very close access to Lake Shore Drive for fast Uber/Lyft access. Chicago's Magnificent Mile is just a quick 11 minute drive on LSD with Chicago Cubs' Wrigley Field just an 8 minute drive away (depending on traffic times of course). This is a central location for a great taste of Chicago.

A spacious studio layout is highlighted by a comfortable futon, partial room divider, and a flat-screen TV mounted on the wall. A simple desk and chair provide a functional workspace. Soft natural light filters through the modern window treatments, enhancing the overall brightness of the room.

Apartment in Chicago

4.68 out of 5 average rating, 72 reviews

Studio in Chicago's Edgewater by Lakefront/LSD/CTA

New basement studio construction in Chicago's historic Edgewater a few blocks from Lakefront beach amenities (weather-permitting). Easy access to public CTA and Redline trains (a block away), with very close access to Lake Shore Drive for fast Uber/Lyft access. Chicago's Magnificent Mile is just a quick 11 minute drive on LSD with Chicago Cubs' Wrigley Field just an 8 minute drive away (depending on traffic times of course). This is a central location for a great taste of Chicago.

Guest favorite

A well-lit living area features a striped sofa accompanied by two modern armchairs. A wooden coffee table sits in the center, complemented by a patterned rug. Shelves display an array of silverware and decorative items, adding character and visual interest to the space.

Condo in Chicago

4.93 out of 5 average rating, 261 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.

Top guest favorite

The spacious garden studio features a cozy living area with a textured sofa adorned with decorative pillows. A stylish coffee table is positioned in front, complementing an adjacent dining area. The kitchenette showcases modern appliances, while warm lighting enhances the welcoming ambiance.

Apartment in Chicago

4.96 out of 5 average rating, 93 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.

Superhost

A spacious king size bed is dressed in a dark blue patterned quilt, complemented by decorative pillows. A vibrant red throw rests at the foot of the bed. The room features wooden accents, a mirror, and a small bookshelf. Decorative wall hangings add character.

Guest suite in Chicago

4.86 out of 5 average rating, 379 reviews

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.

Guest favorite

A shared common room features a king-sized bed with dark bedding layered over gray sheets. A television sits on a nearby black dresser, and a wooden nightstand is positioned next to the bed. Natural light enters through partially open window blinds.

Shared room in Chicago

4.83 out of 5 average rating, 181 reviews

05a. Common Room King

We have a King-sized bed in a Common Room. This is in a shared common room space. Up to 3 other guests my be booked in this room. The room has limited storage and NO DOOR. This space is best for those with little to no bags. Breakfast is included in your stay. We keep the pantry stocked with eggs, bacon, milk, orange juice, jam, bread, fruit, pancake mix, coffee and tea. Any of these items can be used to make yourself breakfast in the morning.

A bright and airy bedroom features large windows with natural light streaming through light curtains. A spacious bed is made with crisp white linens, complemented by a plush blue throw. Two bedside lamps are positioned on either side, while a bench sits at the foot of the bed.

Apartment in Chicago

4.73 out of 5 average rating, 161 reviews

Cozy 1 bdr in Edgewater close to Red L & Loyola

Get cozy in this beautifully designed studio that sleeps 2 guests. The thoughtful, contemporary design combines elegant details and modern furnishings. Its conveniently located within steps to fantastic shops, cafes, restaurants and bars. Ideal for couples, group of 2 or solo travelers. Its conveniently located within steps to coffee shops, restaurants, bars, nightlife, Whole Foods, Loyola university, the beach and Red Line