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Holiday Homes in South Side

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Check prices for these dates

Next weekend
5 Dec - 7 Dec
In two weeks
12 Dec - 14 Dec
In one month
26 Dec - 28 Dec
In two months
23 Jan - 25 Jan

Featured Holiday Homes in South Side and around

Fridge, microwave, oven, stovetop
Stylish 3BR Gem in Prime Location

Holiday Home in Near South Side

Stylish 3BR Gem in Prime Location
Microwave, oven, stovetop
Pleasant 3-bedroom house in Sauk Village

Holiday Home in Sauk Village

2.0 star property
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 €120
includes taxes & fees
1 Dec - 2 Dec
Pleasant 3-bedroom house in Sauk Village
Beach nearby
Dunes Escape - Minutes from Indiana Dunes National Park

Holiday Home in 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 €272
includes taxes & fees
1 Dec - 2 Dec
Dunes Escape - Minutes from Indiana Dunes National Park
Smart TV
Getaway Near ORD With Great Local Amenities

Holiday Home in Des Plaines

9.0 out of 10, Wonderful, (4)
"Very nice and clean place to stay at. Great communication from property manager. I would absolutely stay here again!"
United States
Stephanie G.
The price is €248
includes taxes & fees
9 Dec - 10 Dec
Getaway Near ORD With Great Local Amenities
Fridge, microwave, oven, stovetop
Spacious 3br home near Chicago, fenced yard for pets

Holiday Home in Richton Park

2.0 star property
9.0 out of 10, Wonderful, (13)
"Awesome stay!"
United States
Patrick J.
The price is €277
includes taxes & fees
30 Nov - 1 Dec
Spacious 3br home near Chicago, fenced yard for pets
Exterior detail
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

Holiday Home in Robertsdale

2.0 star property
10.0 out of 10, Exceptional, (12)
"Very clean in a safe neighborhood. I would stay here again"
United States
Charles W.
The price is €179
includes taxes & fees
5 Dec - 6 Dec
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.
Fridge, microwave, oven, stovetop
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

Holiday Home in Worth

9.6 out of 10, Exceptional, (53)
"Perfect place for an 8 person golf trip! "
United States
Griffin P.
The price is €294
includes taxes & fees
7 Dec - 8 Dec
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Exterior
Woodscape Haven · Cozy 3BR Escape

Holiday Home in Miller Beach

10.0 out of 10, Exceptional, (1)
"Lovely, relaxing and clean. Host is very responsive. "
United States
Jennifer L.
The price is €320
includes taxes & fees
4 Dec - 5 Dec
Woodscape Haven · Cozy 3BR Escape
Interior
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Holiday Home in Lockport

10.0 out of 10, Exceptional, (4)
"Amazing property had everything we need! "
United States
Rachel
The price is €338
includes taxes & fees
30 Nov - 1 Dec
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Fridge, microwave, oven, stovetop
Honeycomb Hideout w/ 2 bedrooms

Holiday Home in Gary

The price is €374
includes taxes & fees
26 Nov - 27 Nov
Honeycomb Hideout w/ 2 bedrooms
Exterior
Coziest estate home 20 minutes to downtown

Holiday Home in 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 €354
includes taxes & fees
1 Dec - 2 Dec
Coziest estate home 20 minutes to downtown
Exterior detail
Vintage Urban Retreat

Holiday Home in Oak Park

10.0 out of 10, Exceptional, (12)
"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 €414
includes taxes & fees
1 Dec - 2 Dec
Vintage Urban Retreat
Fridge, microwave, oven, stovetop
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS

Holiday Home in Skokie

10.0 out of 10, Exceptional, (34)
"Great!"
United States
Laura N.
The price is €583
includes taxes & fees
1 Dec - 2 Dec
Luxe Haus of Love—Renovated 1938 Cape Cod —Heated FLRS
Fitness facility
Theater • Game Room • Gym • Firepit • 4BR Home

Holiday Home in Belmont Cragin

2.0 star property
The price is €489
includes taxes & fees
2 Dec - 3 Dec
Theater • Game Room • Gym • Firepit • 4BR Home
Beach
Cozy Family Getaway- 4 Blocks From The Beach!

Holiday Home in Miller Beach

Cozy Family Getaway- 4 Blocks From The Beach!
Private kitchen
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking

Holiday Home in La Grange Highlands

10.0 out of 10, Exceptional, (2)
"Good communication from beginning to the end. Will definitely stay at this property again on my next Chicago vacation."
United States
Arnie B.
The price is €266
includes taxes & fees
30 Nov - 1 Dec
Guesthouse Gem 2BR, Smart TVs, W/D, & Parking
Outdoor dining
✽ Charming Cottage ✽ close to College/Town/Station

Holiday Home in Wheaton

10.0 out of 10, Exceptional, (54)
"Great place for a family visit to Wheaton! Thanks!"
United States
Lisa
The price is €274
includes taxes & fees
3 Dec - 4 Dec
✽ Charming Cottage ✽ close to College/Town/Station
Dining
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard

Holiday Home in Lombard

9.6 out of 10, Exceptional, (15)
"I had a great stay over the weekend with my family it was very relaxing and peaceful "
United States
Tennika W.
The price is €271
includes taxes & fees
30 Nov - 1 Dec
PROMO 10% MONTHLY DISCOUNT! Comfy Home w Access to Major Roads/Hwys, Huge Yard
Microwave, oven, stovetop, dishwasher
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

Holiday Home in Maywood

7.8 out of 10, Good, (13)
"Very nice place "
United States
Elliot H.
The price is €216
includes taxes & fees
30 Nov - 1 Dec
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
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

Motel 6 - Chicago, IL

Motel 6 - Chicago, IL

10/10 Excellent
"😊"
Melissa 1-night trip
Posted 5 days ago
Motel 6 - Chicago, IL

Find out more about South Side

South Side Holiday Homes information

Number of reviews
227
Accommodation
97 Holiday Homes
Lowest Price
€120
Highest Price
€585

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