Vacation rentals in Kathy Osterman Beach

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Top-rated vacation rentals in Kathy Osterman Beach

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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 West Rogers Park

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.

4.99 out of 5 average rating, 119 reviews

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 Edgewater

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!

4.98 out of 5 average rating, 175 reviews

Top guest favorite

A charming coach house is enveloped in lush greenery, with ivy climbing its brick exterior. Tall birch trees stand on either side, framing a large window that allows natural light to illuminate the interior. The surrounding area features a tranquil courtyard with paving stones.

Apartment in Edgewater

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.

4.96 out of 5 average rating, 167 reviews

Top guest favorite

Apartment in Edgewater

Modern 1 BR Near the L, Beach - Bright and Sunny!

Our bright and modern 1-bedroom apartment awaits in Chicago’s Edgewater neighborhood! This private, sun-filled space features a separate entrance and is designed or comfort and convenience. The bedroom includes a king-size bed and the living room offers a pull-out sofa. You’re within walking distance of Hollywood Beach and the lakefront, The Red Line “L” train is just a short walk away. Andersonville is only 10 minutes away, where you’ll find charming shops, cafés, and great dining options.

5.0 out of 5 average rating, 22 reviews

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 Edgewater

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.

4.79 out of 5 average rating, 185 reviews

Top guest favorite

Apartment in Uptown

Top Rated 3bed Delight-Walk to shops & restaurants

Experience a "top-rated" stay in this well appointed, newly remolded 1904 Greystone. Just steps from Clark St, our 3BR (1 King, 2 Queens) is "hands down one of the best". Enjoy a chef’s kitchen stocked with every detail, 3 Roku TVs, and in-unit laundry for a true home-away-from-home feel. Stroll to Andersonville’s best eats and guest favorite shops, attend concerts and shows or take a short drive to the nearby microbreweries, beach and Wrigley, it's also just a 15 min drive to Downtown.

5.0 out of 5 average rating, 52 reviews

Top guest favorite

A modern, open space is revealed, featuring light wood flooring and a green accent wall. To the left, a kitchen area is visible with sleek cabinetry, while a cozy seating area with a television can be seen in the background, promoting a comfortable gathering space.

Apartment in Edgewater

Edgewater Garden Getaway

Edgewater Garden Getaway, is a newly renovated space with a craftsmen touch and elevated charm. Walking distance to Lake Michigan and Andersonville neighborhood and next door to great restaurants, the red line public transite, grocery store and antigüedad shops. Private entrance and access to the back yard garden area. if Chicago is your next destinación, this is the perfect space to recharge and rest between adventures.

4.9 out of 5 average rating, 77 reviews

Top guest favorite

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.

Apartment in Edgewater

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.

4.98 out of 5 average rating, 167 reviews

Top guest favorite

Apartment in Andersonville

Modern Andersonville 1BR | Walk to Lake & Cafés

This thoughtfully designed, sun-filled, clean 1 Bedroom 1 Bath is located in the heart of Andersonville- just steps to Chicago's best cafés, boutiques, and lakefront trails. Perfect for remote workers, couples and solo travelers looking for a True Chicago neighborhood experience. Having been in our family since 1984, we take pride in providing guests with an experience that blends history with modern day comforts.

5.0 out of 5 average rating, 30 reviews

Guest favorite

The living room displays a spacious gray sofa complemented by an accent chair in a warm tone. A circular coffee table sits at the center, while a large flat-screen TV is mounted on a light wood media unit. Natural light filters through the windows, enhancing the tranquil atmosphere.

Apartment in Edgewater

Guest Favorite | In Unit Laundry | New Renovation

1st-floor unit with an 8-step staircase to access. Welcome to your charming 1BR|1BA retreat in the heart of Andersonville! This cozy apartment offers a comfortable living space, fully equipped kitchen, central heating and AC, in-unit washer and dryer, and a peaceful bedroom for a restful stay. Just steps from vibrant shops, restaurants, and cafes, plus nearby parks, nightlife, and easy public transit access.

4.91 out of 5 average rating, 92 reviews

Top guest favorite

A modern kitchen is showcased with sleek black countertops and white cabinetry. A tall chair is situated at the kitchen island, providing seating for one. Stainless steel appliances, including a gas stove and microwave, are visible, complemented by warm yellow walls that enhance the space's brightness.

Apartment in Edgewater

Andersonville Garden Living

This is an amazing garden level apartment right off Clark st. with all the shops and restaurants right down the block. Grab a coffee at the Coffee Studio or a drink at Little Bad Wolf . This unit has a brand new kitchen and has a Smart TV with Netflix and a huge living room to hang out, and new bathroom with a large shower. It also has a private bedroom and access to laundry.

4.83 out of 5 average rating, 160 reviews

Superhost

Apartment in Uptown

The Velvet Manor | 2BR Boutique Stay

Welcome to The Velvet Manor, a moody, designer-curated 2-bedroom retreat in the heart of Andersonville. Unwind in richly layered interiors featuring a king primary bedroom, one queen bedroom, dramatic living and dining spaces, and thoughtful boutique-hotel touches throughout. Enjoy one private garage parking space, free street parking, and room for up to 4 guests.

5.0 out of 5 average rating, 3 reviews