Holiday rentals in Kathy Osterman Beach
Find and book unique accommodation on Airbnb
Top-rated holiday rentals in Kathy Osterman Beach
Guests agree: these stays are highly rated for location, cleanliness and more.
Flat in Edgewater
4.93 out of 5 average rating, 377 reviewsRavenswood 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
Flat in Edgewater
4.9 out of 5 average rating, 291 reviewsEdgewater 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
Flat in Uptown
4.97 out of 5 average rating, 260 reviewsCozy 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
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Kathy Osterman Beach holiday rentals
Other great holiday rentals in Kathy Osterman Beach
Guest suite in Andersonville
4.85 out of 5 average rating, 316 reviewsCozy and Private Andersonville Retro Studio
18–25 Aug
Guest suite in Lincoln Square
4.97 out of 5 average rating, 356 reviewsPrivate suite in Lincoln Square
13–20 Dec
Apartment in East Rogers Park
4.94 out of 5 average rating, 181 reviewsPvt 1bdr Rogers Park, Loyola, Northwestern.
25 Sept – 2 Oct
Flat in Andersonville
4.98 out of 5 average rating, 184 reviewsFoster Flat - Retreat to your Home Away from Home
18–25 Jun
Guest suite in Lincoln Square
4.92 out of 5 average rating, 400 reviewsPrivate Lincoln Square Garden Apt
18–25 Nov
Flat in East Rogers Park
4.95 out of 5 average rating, 264 reviewsHuge Victorian near Loyola 2bd Apt
12–19 Jan
Flat in Andersonville
4.96 out of 5 average rating, 247 reviewsSunny, Cozy, Colorful Andersonville
28 Aug – 4 Sept
Flat in Lincoln Square
4.96 out of 5 average rating, 316 reviewsBright family-friendly Lincoln Square 2-bed 1-bath
28 Sept – 5 Oct
Flat in East Rogers Park
4.95 out of 5 average rating, 126 reviewsThe Lodge Chicago
15–22 Jun
Flat in Uptown
4.8 out of 5 average rating, 102 reviewsCharming Uptown Studio - Clean & Close to Train!
11–18 Mar
Guest suite in East Rogers Park
4.96 out of 5 average rating, 101 reviews1BR Historic Rogers Park/West Ridge unit- Sleeps 4
12–19 Jan
Apartment in Lincoln Square
4.98 out of 5 average rating, 325 reviewsLincoln Square Gem!
15–22 Sept
Destinations to explore
- Downtown Chicago Holiday rentals
- Milwaukee Holiday rentals
- Lake Geneva Holiday rentals
- Lake Michigan Beach Holiday rentals
- Saugatuck Holiday rentals
- Evanston Holiday rentals
- Holland Holiday rentals
- South Haven Holiday rentals
- Naperville Holiday rentals
- South Side Holiday rentals
- South Bend Holiday rentals
- Chicago Holiday rentals
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom