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Holiday Homes in South Side

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Our top choices for South Side holiday homes

Your Home Away From Home in Sauk Village

Your Home Away From Home in Sauk Village
2.0 star property
Sauk Village
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! "
United States
Aaron K.
The price is NZ$295
includes taxes & fees
31 Jan - 1 Feb 2026
Your Home Away From Home in Sauk Village

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
2.0 star property
Merrilville
The price is NZ$646
includes taxes & fees
30 Jan - 31 Jan 2026
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
2.0 star property
Richton Park
9.0 out of 10, Wonderful, (14)
"Really cute house! Very comfortable beds. Clean and well maintained. "
United States
Samantha D.
The price is NZ$538
includes taxes & fees
5 Jan - 6 Jan 2026
Spacious 3br home near Chicago, fenced yard for pets

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.
2.0 star property
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."
United States
Karen D.
The price is NZ$310
includes taxes & fees
5 Jan - 6 Jan 2026
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Honeycomb Hideout w/ 2 bedrooms

Honeycomb Hideout w/ 2 bedrooms
Gary
The price is NZ$728
includes taxes & fees
2 Jan - 3 Jan 2026
Honeycomb Hideout w/ 2 bedrooms

Dunes Escape - Minutes from Indiana Dunes National Park

Dunes Escape - Minutes from Indiana Dunes National Park
Miller 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!"
United States
Braden S.
The price is NZ$507
includes taxes & fees
6 Jan - 7 Jan 2026
Dunes Escape - Minutes from Indiana Dunes National Park

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (55)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
The price is NZ$583
includes taxes & fees
4 Jan - 5 Jan 2026
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Coziest estate home 20 minutes to downtown

Coziest estate home 20 minutes to downtown
Willow 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!"
United States
Gabriela N.
The price is NZ$685
includes taxes & fees
9 Jan - 10 Jan 2026
Coziest estate home 20 minutes to downtown

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (5)
"Amazing property had everything we need! "
United States
Rachel
The price is NZ$643
includes taxes & fees
12 Jan - 13 Jan 2026
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Vintage Urban Retreat

Vintage Urban Retreat
Oak Park
10.0 out of 10, Exceptional, (14)
"This location was very convenient, and in close proximity to both downtown Oak Park, and the greater Chicago area."
United States
Thomas P.
The price is NZ$857
includes taxes & fees
4 Jan - 5 Jan 2026
Vintage Urban Retreat

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (19)
"Great place Great location "
United States
Josh W.
The price is NZ$703
includes taxes & fees
5 Jan - 6 Jan 2026
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

Luxury Suite in Glen Ellyn, IL USA

Luxury Suite in Glen Ellyn, IL USA
Glen Ellyn
9.6 out of 10, Exceptional, (10)
"Was very comfortable. Had everything we needed except wash clothes. Walmart really close. "
United States
Debra B.
Luxury Suite in Glen Ellyn, IL USA

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
8.0 out of 10, Very good, (20)
"Very nice place "
United States
Elliot H.
The price is NZ$407
includes taxes & fees
4 Jan - 5 Jan 2026
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (55)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is NZ$533
includes taxes & fees
1 Jan - 2 Jan 2026
✽ Charming Cottage ✽ close to College/Town/Station

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Gary
8.6 out of 10, Excellent, (17)
"i had a good time here. the house was great. thank you"
United States
Alvaro C.
The price is NZ$776
includes taxes & fees
5 Jan - 6 Jan 2026
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

Enamored in Elmhurst

Enamored in Elmhurst
2.0 star property
Elmhurst
10.0 out of 10, Exceptional, (14)
"Great stay"
United States
Aaron B.
The price is NZ$849
includes taxes & fees
7 Jan - 8 Jan 2026
Enamored in Elmhurst

20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill

20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill
Gary
10.0 out of 10, Exceptional, (4)
"Very nice property. Kids loved staying here! "
United States
Sydney D.
The price is NZ$785
includes taxes & fees
5 Jan - 6 Jan 2026
20mins from beach, 10guests/WIFI/1.2 baths/ping pong/pool table/treadmill

Wonderful in Wood Dale, right by O’Hare airport!

Wonderful in Wood Dale, right by O’Hare airport!
Wood Dale
10.0 out of 10, Exceptional, (18)
"Great property and great host!"
United States
Darin H.
The price is NZ$679
includes taxes & fees
1 Jan - 2 Jan 2026
Wonderful in Wood Dale, right by O’Hare airport!

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.2 out of 10, Wonderful, (5)
"Charming property in a quiet neighborhood. Host were exceptionally accommodating and replied promptly with questions. Would happily stay in this home again."
United States
Michael H.
The price is NZ$490
includes taxes & fees
5 Jan - 6 Jan 2026
Cozy Home by O'Hare + EV Plug

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.8 out of 10, Excellent, (38)
"Great place to stay. Plenty of backyard space. "
United States
Terrence M.
The price is NZ$562
includes taxes & fees
14 Jan - 15 Jan 2026
LUXE 3 BR, 2 BA + Hot Tub
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

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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