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Our top choices for South Side vacation homes

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is ¥19,876
¥92,008 total
includes taxes & fees
Jul 6 - Jul 7
Near Lake and Museum • Modern • Game Area

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
10.0 out of 10, Exceptional, (11 reviews)
The price is ¥94,892
¥172,086 total
includes taxes & fees
Jun 25 - Jun 26
ENVITAE Hotel, 4BR Luxury Modern Apartments

Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
10.0 out of 10, Exceptional, (1 review)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is ¥25,967
¥33,398 total
includes taxes & fees
Jun 8 - Jun 9
Attractive Coach House Apartment for rent in Oak Park.

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
The price is ¥30,776
¥73,246 total
includes taxes & fees
Jun 9 - Jun 10
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

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, (27 reviews)
"I had a fun stay "
United States
Jusu K.
The price is ¥22,937
¥31,974 total
includes taxes & fees
Jun 9 - Jun 10
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

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, (28 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is ¥23,803
¥47,757 total
includes taxes & fees
Jun 8 - Jun 9
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
9.8 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is ¥28,852
¥51,642 total
includes taxes & fees
Jun 9 - Jun 10
✽ Charming Cottage ✽ close to College/Town/Station

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central
Lisle
9.6 out of 10, Exceptional, (29 reviews)
"Vic and his staff were extremely attentive. Thank you for a great stay"
United States
Brian N.
The price is ¥21,038
¥49,305 total
includes taxes & fees
Jun 8 - Jun 9
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Miller Beach
8.8 out of 10, Excellent, (48 reviews)
"Great place and great location "
United States
Travis B.
The price is ¥49,811
¥128,978 total
includes taxes & fees
Jun 14 - Jun 15
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
10.0 out of 10, Exceptional, (1 review)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is ¥29,695
¥62,816 total
includes taxes & fees
Jun 9 - Jun 10
Entire home in Lockport, Illinois

Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat`l Park

Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat`l Park
Miller Beach
8.6 out of 10, Excellent, (29 reviews)
"A plus thanks"
United States
Anonymous traveler
The price is ¥44,785
¥126,887 total
includes taxes & fees
Jun 17 - Jun 18
Modern Beach Bungalow, Hot tub, Firepit, Foosball, IN Dunes Nat`l Park

Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (25 reviews)
"The host was great and communication for her to respond was great. The amenities were good as well"
United States
Shantel U.
The price is ¥32,747
¥73,443 total
includes taxes & fees
Jun 8 - Jun 9
Spacious 3br home near Chicago, fenced yard for pets

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Merrillville
9.8 out of 10, Exceptional, (6 reviews)
"Me and my partner had so much fun! The host was very kind, we had our privacy and everything we could've needed during our stay. We truly had a great time! I'd love to come back someday!"
United States
Janina
The price is ¥48,087
¥75,939 total
includes taxes & fees
Jun 7 - Jun 8
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

3-bedroom hillside property in woods with fireplace and lake view

3-bedroom hillside property in woods with fireplace and lake view
Lemont
6.0 out of 10, (6 reviews)
"Was very nice to stay owner was very nice it was a pleasant stay for me ,my family and my friends will recommend . "
United States
Jennifer D.
The price is ¥30,615
¥43,382 total
includes taxes & fees
Jul 7 - Jul 8
3-bedroom hillside property in woods with fireplace and lake view

Lovely 3-bedroom house in Villa Park with WiFi and AC

Lovely 3-bedroom house in Villa Park with WiFi and AC
Villa Park
9.0 out of 10, Wonderful, (2 reviews)
"Location was great."
United States
Jessica F.
The price is ¥33,324
¥78,805 total
includes taxes & fees
Jun 8 - Jun 9
Lovely 3-bedroom house in Villa Park with WiFi and AC

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.6 out of 10, Exceptional, (9 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is ¥27,410
¥55,387 total
includes taxes & fees
Jun 28 - Jun 29
Cozy Home by O'Hare + EV Plug

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is ¥31,449
¥56,371 total
includes taxes & fees
Jun 9 - Jun 10
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is ¥29,453
¥58,223 total
includes taxes & fees
Jul 7 - Jul 8
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Your Next Vacation Home

Your Next Vacation Home
Oakton
9.4 out of 10, Exceptional, (76 reviews)
"Well welcoming and kind. I’m glad we stayed here. "
United States
Justi N.
The price is ¥35,488
¥61,971 total
includes taxes & fees
Jun 8 - Jun 9
Your Next Vacation Home

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, (9 reviews)
"Amazing property had everything we need! "
United States
Rachel
The price is ¥36,802
¥68,769 total
includes taxes & fees
Jun 9 - Jun 10
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
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 Vacation Homes information

Number of reviews
329
Accommodation
104 Vacation Homes
Lowest Price
¥31,974
Highest Price
¥172,086

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