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Holiday Homes in Southwest Side
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Our top choices for Southwest Side holiday homes
Holiday Home in Richton Park
Spacious 3br home near Chicago, fenced yard for pets9.0 out of 10, Wonderful, (14)
"Awesome stay!"
Patrick J.
The price is €272
includes taxes & fees
21 Dec - 22 Dec
Holiday Home in Sauk Village
Your Home Away From Home in Sauk Village10.0 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 €129
includes taxes & fees
30 Dec - 31 Dec
Holiday Home in Robertsdale
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.9.8 out of 10, Exceptional, (15)
"Wonderful property and nice owners. I definitely recommend and will stay again if I'm ever in the area."
Karen D.
The price is €174
includes taxes & fees
21 Dec - 22 Dec
Holiday Home in Worth
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi9.6 out of 10, Exceptional, (54)
"Perfect place for an 8 person golf trip! "
Griffin P.
The price is €279
includes taxes & fees
12 Jan - 13 Jan 2026
Holiday Home in Lockport
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!10.0 out of 10, Exceptional, (4)
"Amazing property had everything we need! "
Rachel
The price is €332
includes taxes & fees
13 Jan - 14 Jan 2026
Holiday Home in Des Plaines
Getaway Near ORD With Great Local Amenities9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
Stephanie G.
The price is €241
includes taxes & fees
11 Jan - 12 Jan 2026
Holiday Home in Willow Springs
Coziest estate home 20 minutes to downtown8.8 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 €348
includes taxes & fees
28 Dec - 29 Dec
Holiday Home in Elmhurst
LUXE 3 BR, 2 BA + Hot Tub8.8 out of 10, Excellent, (38)
"A really nice house, clean and well kept. Neighborhood is older but nice and quiet. Close to highway and lots of restaurants. The owner was very responsive and great to work with. I plan on using this VRBO again in future. Backyard was fenced in and I might bring my pets next time. "
Scott C.
The price is €246
includes taxes & fees
21 Dec - 22 Dec
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 Southwest Side Hotel Reviews
Homewood Suites by Hilton Chicago Downtown South Loop
10/10 Excellent
Find out more about Southwest Side
Southwest Side Holiday Homes information
Number of reviews | 301 |
|---|---|
Accommodation | 344 Holiday Homes |
Lowest Price | €129 |
Highest Price | €463 |
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