Vacation rentals in Kathy Osterman Beach

Top guest favorite

Guest favorite

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.

Family · Location · Laundry

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Guest favorite

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.

Family · Location · TV

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Guest favorite

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.

Location · Family · Quiet

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.

Location · Family · Layout

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Guest favorite

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.

Family · Location · Parks

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Guest favorite

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. There is easy access to Lake Shore Drive, Evanston and downtown.

Location · Family · Condition

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Guest favorite

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.

Value · Family · Layout

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Guest favorite

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.

Location · Value · Laundry

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Guest favorite

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).

Value · Location · Getting around

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Guest favorite

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.

Location · Value · Quiet

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.

Location · Parking · Kitchen

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Guest favorite

Andersonville Living

Sunny 3 Bedroom 1 Bath located in Andersonville right off Clark St. with its shopping, bars and restaurants. The apartment has vintage charm with original woodwork and floors as well as modern amenities such as the new kitchen and central AC. There is a large sunny back deck for sipping your morning coffee, wifi, cable and Amazon for your media needs.

Family · Location · Outdoor spaces