Holiday rentals in Kathy Osterman Beach

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Top-rated holiday rentals in Kathy Osterman Beach

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

Guest favourite

Flat in Edgewater

4.93 out of 5 average rating, 377 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.

26 Dec – 2 Jan

£95 per night
Guest favourite

Flat in Edgewater

4.9 out of 5 average rating, 291 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.

25 Dec – 1 Jan

£129 per night
Guest favourite

Flat in Uptown

4.97 out of 5 average rating, 260 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.

21–28 Aug

£111 per night

Popular amenities for Kathy Osterman Beach holiday rentals

Other great holiday rentals in Kathy Osterman Beach

Superhost

Guest suite in Andersonville

4.85 out of 5 average rating, 316 reviews

Cozy and Private Andersonville Retro Studio

18–25 Aug

£122 per night
Guest favourite

Guest suite in Lincoln Square

4.97 out of 5 average rating, 356 reviews

Private suite in Lincoln Square

13–20 Dec

£104 per night
Guest favourite

Apartment in East Rogers Park

4.94 out of 5 average rating, 181 reviews

Pvt 1bdr Rogers Park, Loyola, Northwestern.

25 Sept – 2 Oct

£109 per night
Guest favourite

Flat in Andersonville

4.98 out of 5 average rating, 184 reviews

Foster Flat - Retreat to your Home Away from Home

18–25 Jun

£158 per night
Guest favourite

Guest suite in Lincoln Square

4.92 out of 5 average rating, 400 reviews

Private Lincoln Square Garden Apt

18–25 Nov

£108 per night
Guest favourite

Flat in East Rogers Park

4.95 out of 5 average rating, 264 reviews

Huge Victorian near Loyola 2bd Apt

12–19 Jan

£158 per night
Guest favourite

Flat in Andersonville

4.96 out of 5 average rating, 247 reviews

Sunny, Cozy, Colorful Andersonville

28 Aug – 4 Sept

£172 per night
Guest favourite

Flat in Lincoln Square

4.96 out of 5 average rating, 316 reviews

Bright family-friendly Lincoln Square 2-bed 1-bath

28 Sept – 5 Oct

£135 per night
Guest favourite

Flat in East Rogers Park

4.95 out of 5 average rating, 126 reviews

The Lodge Chicago

15–22 Jun

£165 per night
Superhost

Flat in Uptown

4.8 out of 5 average rating, 102 reviews

Charming Uptown Studio - Clean & Close to Train!

11–18 Mar

£144 per night
Guest favourite

Guest suite in East Rogers Park

4.96 out of 5 average rating, 101 reviews

1BR Historic Rogers Park/West Ridge unit- Sleeps 4

12–19 Jan

£116 per night
Guest favourite

Apartment in Lincoln Square

4.98 out of 5 average rating, 325 reviews

Lincoln Square Gem!

15–22 Sept

£152 per night

Destinations to explore