Vacation rentals in Kathy Osterman Beach

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Top-rated vacation rentals in Kathy Osterman Beach

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Guest favorite

Apartment in Edgewater

4.93 out of 5 average rating, 380 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.

Dec 21 – 28

G$19,038 GYD per night

Guest favorite

Apartment in Edgewater

4.9 out of 5 average rating, 294 reviews

Edgewater escape, charming 2 BR, Rooftop Solar

Self check-in to a charming 2-bedroom + living/dining room, private entrance garden apartment, close to: the red line to downtown or Evanston, the lake, theaters, restaurants, and parks. Edgewater is known for tree-lined streets, quiet, safe, diverse, & as a friendly neighborhood. We provide breakfast foods (coffee, tea, fresh fruit, milk, cereal, bread and homemade jam). There is a microwave, small fridge & induction stovetop. You're limiting carbon emissions with solar & heat/ac pumps.

Nov 19 – 26

G$25,130 GYD per night

Guest favorite

Apartment in Uptown

4.96 out of 5 average rating, 264 reviews

Cozy loft in Chicago's Uptown

Located in the heart of Uptown, we offer a private, 3rd floor/walk-up, smoke-free studio apartment in a vintage Queen Anne (hosts live on 1st floor; small family on 2nd). The Aragon Ballroom, Riviera Theater and the legendary Green Mill Jazz club all within a 5-minute walk. New!Andersonville, recently voted the coolest neighborhood in US (Timeout’s survey) is only a 15-minute stroll. The CTA's Red Line/Wilson station is 3 blocks away. Overnight street-parking decals also available for guests.

Oct 8 – 15

G$24,282 GYD per night

Guest favorite

Guest suite in Lincoln Square

5.0 out of 5 average rating, 292 reviews

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

Sep 29 – Oct 6

G$29,288 GYD per night

Guest favorite

Apartment in Andersonville

4.92 out of 5 average rating, 108 reviews

Edgewater, private, charming coach house 2 (of 2) Licensed by the City of Chicago 2209376

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.

Oct 31 – Nov 7

G$25,052 GYD per night

Guest favorite

Apartment in Lincoln Square

4.94 out of 5 average rating, 190 reviews

Spacious, light-drenched studio-private entrance!

Sun-filled private apartment in Lincoln Square! Spacious & well-appointed studio apartment features newly renovated kitchen and 1.5 baths (spa shower!) Located in the Lincoln Square neighborhood, you’ll be steps to restaurants, cafes, pubs & shopping. Close to CTA Brown Line (Rockwell) stop, as well as Western, Foster & Lawrence buses. Just 3.4 miles to Wrigley Field. One block to Swedish Covenant Hospital. Short bus/ride-share to Andersonville, Chicago Lakefront & Foster Beach! Kid friendly.

Jul 10 – 17

G$23,539 GYD per night

Guest favorite

Guest suite in Andersonville

4.96 out of 5 average rating, 317 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.

Feb 14 – 21

G$18,671 GYD per night

Superhost

Apartment in Edgewater

4.79 out of 5 average rating, 126 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.

Feb 18 – 25

G$29,811 GYD per night

Superhost

Apartment in Andersonville

4.82 out of 5 average rating, 434 reviews

Lovely Andersonville Apt with Ideal Location

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).

Nov 9 – 16

G$23,136 GYD per night

Superhost

Apartment in East Rogers Park

4.89 out of 5 average rating, 105 reviews

LAKESIDE PIED `A TERRE STEPS TO BEACH

This gem is steps from Hartigan Beach, an eclectic mix of eateries, small theater venues, public transportation and Fine Wines & Spirits. You'll love my place because of the coziness and proximity to a swimming beach, on a friendly tree lined street. Conveniently situated between Loyola and Northwestern Universities. Rent a Divvy bike, call UBER/LYFT, rent a car and explore all that Evanston, Edgewater and Andersonville has to offer!

Oct 19 – 26

G$25,111 GYD per night

Guest favorite

Guest suite in Lincoln Square

4.94 out of 5 average rating, 176 reviews

Lincoln Square In-laws Suite: Private Entrance

Garden apartment room with private entrance and ensuite bathroom. All the amenities you'll need for either a work trip, city sightseeing, or just a comfy bed. Located in the vibrant Lincoln Square neighborhood. Only minutes away from the train. Fast wifi, and a large desk for working away from home. P.S. You will most likely find a few beers from a Chicago brewery in the fridge.

Aug 19 – 26

G$23,576 GYD per night

Guest favorite

Apartment in Andersonville

4.98 out of 5 average rating, 166 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.

Mar 1 – 8

G$29,991 GYD per night