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Holiday Homes in South Side
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Our top choices for South Side holiday homes
10.0 out of 10, Exceptional, (1)
"My Experience Was (NOTHING) Short Of Perfect! The Place Is Nice & The Host Was Even Better! I’ll Forsure Be Booking Again! "
Aaron K.
The price is NZ$295
includes taxes & fees
31 Jan - 1 Feb 2026
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Modern 3BR w/Deck · Minutes from I-65. Fenced YardMerrilville
The price is NZ$646
includes taxes & fees
30 Jan - 31 Jan 2026
Spacious 3br home near Chicago, fenced yard for pets
Spacious 3br home near Chicago, fenced yard for petsRichton Park
9.0 out of 10, Wonderful, (14)
"Really cute house! Very comfortable beds. Clean and well maintained. "
Samantha D.
The price is NZ$538
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.Robertsdale
9.8 out of 10, Exceptional, (17)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
Karen D.
The price is NZ$310
includes taxes & fees
5 Jan - 6 Jan 2026
The price is NZ$728
includes taxes & fees
2 Jan - 3 Jan 2026
Dunes Escape - Minutes from Indiana Dunes National Park
Dunes Escape - Minutes from Indiana Dunes National ParkMiller Beach
9.8 out of 10, Exceptional, (36)
"We loved our stay and had a relaxing time in the area. Buying groceries to cook was great with a full kitchen to cook with. Rooms were super nice and also had every accommodation we could need. Definitely will be looking to stay again!"
Braden S.
The price is NZ$507
includes taxes & fees
6 Jan - 7 Jan 2026
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
*The Comfy King Ranch*King Bed Suite*Fast Wi-FiWorth
9.6 out of 10, Exceptional, (55)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is NZ$583
includes taxes & fees
4 Jan - 5 Jan 2026
Coziest estate home 20 minutes to downtown
Coziest estate home 20 minutes to downtownWillow Springs
8.8 out of 10, Excellent, (16)
"We liked the home, it had everything we needed. We loved having the pool table to play on, that was a hit! The backyard was clean and large, with lots of room! We had the privacy that we needed!"
Gabriela N.
The price is NZ$685
includes taxes & fees
9 Jan - 10 Jan 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top South Side Hotel Reviews
Holiday Inn Chicago – Midway Airport S by IHG
10/10 Excellent
Find out more about South Side
South Side Holiday Homes information
Number of reviews | 310 |
|---|---|
Accommodation | 91 Holiday Homes |
Lowest Price | NZ$295 |
Highest Price | NZ$857 |
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