Holiday Homes in South Side

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Featured Holiday Homes in South Side

Honeycomb Hideout w/ 2 bedrooms

Gary
The price is AU$655
includes taxes & fees
11 Nov - 12 Nov
Honeycomb Hideout w/ 2 bedrooms

A quiet stay while you are away

Oak Park
9.8 out of 10, Exceptional, (32)
"We picked Jay's house because it's located right in the middle of Oak Park where many of Frank Lloyd Wright's works are located, we had so much fun walking the beautiful neighborhood. Jay's property is great too!"
United States
Yimei Z.
The price is AU$315
includes taxes & fees
24 Nov - 25 Nov
A quiet stay while you are away

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 AU$494
includes taxes & fees
1 Dec - 2 Dec
Dunes Escape - Minutes from Indiana Dunes National Park

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
Whiting
10.0 out of 10, Exceptional, (11)
"We had a wonderful time staying here! Everything looks just like the pictures. The hosts were very accommodating and very good with communication. We would definitely stay here again!"
United States
Amina P.
The price is AU$316
includes taxes & fees
11 Nov - 12 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Coziest estate home 20 minutes to downtown

Willow Springs
8.8 out of 10, Excellent, (14)
"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 AU$628
includes taxes & fees
15 Nov - 16 Nov
Coziest estate home 20 minutes to downtown

Pleasant 3-bedroom house 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 AU$209
includes taxes & fees
23 Nov - 24 Nov
Pleasant 3-bedroom house in Sauk Village

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

Worth
9.6 out of 10, Exceptional, (53)
"The owner was amazing house was nice and clean everything was perfect we had a really great time!"
United States
Krystal N.
The price is AU$521
includes taxes & fees
17 Nov - 18 Nov
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Vintage Urban Retreat

Oak Park
10.0 out of 10, Exceptional, (11)
"Loved everything about the place, as advertised in the listing. "
United States
Noah H.
The price is AU$712
includes taxes & fees
11 Nov - 12 Nov
Vintage Urban Retreat

Getaway Near ORD With Great Local Amenities

Des Plaines
9.0 out of 10, Wonderful, (4)
"It's hard get all this for this price. It's not that quiet like other reviews said unless you get up early in the morning. Heating works perfect, it is a bit warmer on the top floor and cooler in the kitchen but nothing to worry about. Parking on the front, walking distance to the grocery stores. 5 stars from me and will come back again."
United States
Dorde U.
The price is AU$439
includes taxes & fees
11 Nov - 12 Nov
Getaway Near ORD With Great Local Amenities

Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

La Grange Highlands
10.0 out of 10, Exceptional, (2)
"Very quiet and private and cl9se to alot of things "
United States
Kenneth W.
The price is AU$398
includes taxes & fees
11 Nov - 12 Nov
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

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

Lockport
10.0 out of 10, Exceptional, (4)
"Great stay! Clean and comfortable and inviting interior. Very convenient fenced in backyard for our dog. James is a gracious, generous host. I highly recommend this property. "
United States
Brian C.
The price is AU$592
includes taxes & fees
9 Dec - 10 Dec
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Hazel Crest
7.4 out of 10, Good, (10)
"Good quiet location "
United States
Augusto D.
The price is AU$519
includes taxes & fees
11 Nov - 12 Nov
Charming 2-bedroom house with WiFi in peaceful Hazel Crest

Newly Remodelled 3-BR Home w/ Firepit and Grill

Miller Beach
10.0 out of 10, Exceptional, (1)
"Lovely, relaxing and clean. Host is very responsive. "
United States
Jennifer L.
The price is AU$555
includes taxes & fees
11 Nov - 12 Nov
Newly Remodelled 3-BR Home w/ Firepit and Grill

Cozy Family Getaway- 4 Blocks From The Beach!

Miller Beach
The price is AU$503
includes taxes & fees
30 Nov - 1 Dec
Cozy Family Getaway- 4 Blocks From The Beach!

✽ Charming Cottage ✽ close to College/Town/Station

Wheaton
10.0 out of 10, Exceptional, (53)
"We loved how cute this house was! It was very convenient for visiting our daughter and nice to have plenty of space and amenities. Our host was very prompt communication. Would definitely stay here again!"
United States
Mary
The price is AU$484
includes taxes & fees
11 Nov - 12 Nov
✽ Charming Cottage ✽ close to College/Town/Station

Superb 3-bedroom house with fitness room in Chicago Heights

Chicago Heights
10.0 out of 10, Exceptional, (1)
"Nice house, very responsive owner"
United States
Michael L.
Superb 3-bedroom house with fitness room in Chicago Heights

PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Lombard
9.6 out of 10, Exceptional, (15)
"We didn’t spend a ton of time at the home, but rather used it as a home base of operations to enjoy what Chicago had to offer. It covered our sleeping needs and was located 30 minutes outside the city to provide us with space from congestion and busyness!"
United States
Jeremy H.
The price is AU$458
includes taxes & fees
11 Nov - 12 Nov
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

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

Lisle
9.6 out of 10, Exceptional, (19)
"Convenient location to family that lives in the area"
United States
Andrea G.
The price is AU$407
includes taxes & fees
11 Nov - 12 Nov
PROMO 15% MONTHLY DISCOUNT! Cozy House, Close to Benedictine & North Central

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

Maywood
7.6 out of 10, Good, (12)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
United States
Johanna
The price is AU$379
includes taxes & fees
11 Nov - 12 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
Richton Park
9.0 out of 10, Wonderful, (13)
"Nice property easy check in. Experience was amazing. Thank you again "
United States
Marshele W.
The price is AU$707
includes taxes & fees
11 Nov - 12 Nov
Spacious 3br home near Chicago, fenced yard for pets
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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