Holiday Homes in South Side

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Featured Holiday Homes in South Side and around

Our top choices for South Side holiday homes

A Home Away From Home!

9.6 out of 10, Exceptional, (7)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

House with garage, outdoor dining and basement bar

7.4 out of 10, Good, (3)
"Property was very clean, warm and welcoming. Beds were comfortable. Property manager was great at checking in, and readily available. The place smells great! Everything is new! We will definitely book again!"
House with garage, outdoor dining and basement bar

LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.6 out of 10, Exceptional, (7)
"Nice place. Looks freshly updated. If you have a hard time with stairs this probably isnt for you as there is 2 flights to climb. Other than that great place"
LuxHome up to 6 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

8.0 out of 10, Very good, (9)
"The place was well maintained and very clean with no issues and the host was great and fast to respond."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

4.0 out of 10, (4)
"There was room enough for everyone. I like the recording ring doorbell. I like bathroom connect to bedroom. I didn’t like the wide open vent in the floor leading to bathroom. The bathroom door is on backwards. The coffee pot was molded. There were plenty of towels and washcloths. The bed is too close to the wall. The neighborhood is nice and quiet. I probably would stay there again but the price was high for the condition of the house. This house needs a lot of maintenance."
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

“The Marlowe” A Couples Getaway

10.0 out of 10, Exceptional, (1)
"Loved everything communication was good definitely a vibe will be booking again "
“The Marlowe” A Couples Getaway

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

9.6 out of 10, Exceptional, (15)
"Large 6 bedroomProsClean & looked new Plenty of space Things to know The neighborhood is not great I would stay here again "
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick

10.0 out of 10, Exceptional, (3)
"We were preparing for our organizations annual fundraiser gala. This home was absolutely amazing. The space was appreciated. "
Modern 4 Bed, 3.5 Bath Home | Near Sox & McCormick

Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-14 guests

9.4 out of 10, Exceptional, (17)
"Very clean and lots of room."
Mayors Manor, Zen Garden Oasis, Hot Tub & Sauna in Central Chicago, 8-14 guests

1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

9.8 out of 10, Exceptional, (9)
"Good location"
1 #23 - 4 Bedroom Condo - McCormick Place, Wintrust Arena, Chinatown

Cheerful 4 bedroom smart home w/ indoor fireplace

8.0 out of 10, Very good, (16)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

South Shore Retreat 5 bedrooms/entertainment

8.0 out of 10, Very good, (3)
"Three weeks later tries to say we didn't pay when we have emails/proof saying otherwise. We checked in at the time, and some guy just comes in the backdoor with towels. Upon checkout, says we didn't leave the key & they had to get a locksmith - we literally saw someone come in with a key (man with towels at check in). Scary neighborhood, misleading advertising, terrible communication. "
South Shore Retreat 5 bedrooms/entertainment

Lakefront property , minutes from McCormick Place and Downtown Chicago.

9.8 out of 10, Exceptional, (7)
"Overall great stay, great host"
Lakefront property , minutes from McCormick Place and Downtown Chicago.

Modern Historic Greystone - Near Lake - Free Prkg

7.0 out of 10, Good, (6)
"Great property in a quiet neighborhood. Not far from downtown and other tourist attractions. 10/10 would recommend. "
Modern Historic Greystone - Near Lake - Free Prkg

Newly Revamped Home - For privacy lovers

10.0 out of 10, Exceptional, (1)
"it was amazing and spacious. it was the perfect home for adults to visit and enjoy themselves."
Newly Revamped Home - For privacy lovers

Hamaline Luxury - Guest House

9.4 out of 10, Exceptional, (3)
"Good stay close to a lot of bus stops very convenient for what we did on our trip. The host was very accommodating and left great instructions on how to access the home. "
Hamaline Luxury - Guest House

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (23)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown

4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

9.6 out of 10, Exceptional, (10)
"Everything in the listing was accurate and clean. Easy to check-in and out. Close to food places and venues."
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

Delightful 5-bedroom house with AC in vibrant Chicago

Delightful 5-bedroom house with AC in vibrant Chicago
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