Search Holiday Homes in South Side

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    today icon
    Change your mind
    Book hotels with free cancellation

Browse Select South Side Holiday Homes

Fridge, microwave, oven, stovetop
Lincoln Park Living - Suite 2!
10.0 out of 10, Exceptional, (2)
"Location can't be beat. 15 min drive to Lincoln Park Zoo though (which was our destination) -not 3 min We were so happy with the location and it had all that we needed stocked. Finding free parking was relativrly easy which is a great plus. But if you are looking for a quiet place, this is not for you. You have to sacrifice peace & quiet for the location"
Lincoln Park Living - Suite 2!
TV
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (4)
"Good host"
Luxury Downtown Penthouse with Private Rooftop!
Private kitchen
Your Next Vacation Home
10.0 out of 10, Exceptional, (9)
"This home was very Beautiful and More Spacious than expected with a Beautiful back yard that we sadly didn’t get to enjoy because of the rain. The house location was great with A lot of stores and restaurants nearby. Next time we have a Family gathering I definitely will be rebooking"
The price is £273
per night
3 Jun - 4 Jun
Your Next Vacation Home
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free
Property grounds
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (2)
"We booked this property for a stay while I took 2 of my sons to the Twins game at Guaranteed Rate Field. Overall it was a great place to stay, it was close to the Field Museum and Lincoln Park Zoo that we went to, and was easy to get to and from the baseball park as well. I do hope they get the tv on the rooftop patio working though, we didn’t really use that space since the tv wasn’t working while we were there. That was the only real downfall of the trip!"
Breathtaking Downtown Penthouse B - Sleeps 11
Property grounds
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (31)
"Great house thank you"
✽ Charming Cottage ✽ close to College/Town/Station
Smart TV, table football, stereo
Freshly Remodeled Cozy Home
10.0 out of 10, Exceptional, (15)
"Place was clean and decor was nice and owner responed very nice to any questions."
Freshly Remodeled Cozy Home
Fridge, microwave, oven, stovetop
Updated Forest Park 3 BR Bungalow
10.0 out of 10, Exceptional, (82)
"This vrbo exceeded expectations from the photos. The vrbo was extemely clean, well maintained, and our dog enjoyed the yard. We also felt very safe walking at night and really enjoyed the proximity to Oak Park attractions, and the green line el stop is a 5 minute walk away. We intend to stay again when visiting the Chicago suburbs!"
Updated Forest Park 3 BR Bungalow
Fridge, microwave, oven, stovetop
Lincoln Park Living - Suite 1
10.0 out of 10, Exceptional, (1)
Lincoln Park Living - Suite 1
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
10.0 out of 10, Exceptional, (150)
"we had a great stay in Lincoln Park. The house worked well for a group of 8 women. The owner was very responsive."
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24
Private kitchen
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
10.0 out of 10, Exceptional, (2)
"My family really enjoyed this townhouse. It was very nice clean, location was perfect. Would definitely stay here again. The host Sherice was very very nice, kind, friendly and patient with my family."
Amazing 4 Bedrm Twnhm-30 Miles to Dwntwn Chicago Private Off Street Parking
Exterior
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
Exterior
Charming Oak Park Home w/ Private Fire Pit!
9.8 out of 10, Exceptional, (8)
"Me and my family stayed there and it has to be my favorite place when visiting family there was more than enough room for local family members to come and visit, the beds were so comfortable and the place was stocked with everything we needed. Communication was perfect we had to stay an extra day and they let us book it with no problem. Would definitely book to stay at again."
Charming Oak Park Home w/ Private Fire Pit!
Beach nearby
Dunes Escape - Minutes from Indiana Dunes National Park
9.8 out of 10, Exceptional, (28)
"We had a great stay! Everything was just as listed! Every area was very clean, kitchen well stocked, plenty of towels provided for our 2 night stay. If i could change anything it would have been to add a nightlight of some sort in the twin room. Unfamiliar place/noises and it was completely dark for my daughter. No lamp or nightlight in that room. Also a few of the cabinet doors need tightened down."
The price is £269
per night
3 Jun - 4 Jun
Dunes Escape - Minutes from Indiana Dunes National Park
Fridge, microwave, oven, stovetop
Brownstone in Gold Coast - Downtown
9.8 out of 10, Exceptional, (8)
"The unit is in a great location and easy to get around. I didn't have a car with me, so I didn't have to worry about parking. It was clean and easy to communicate with the owner. The building itself is an older Chicago building, although the unit has been updated. I really enjoyed my stay!"
Brownstone in Gold Coast - Downtown
Exterior
Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping
9.8 out of 10, Exceptional, (29)
"Comfy bed in primary room! That is the thing I care most about when renting a vacation rental so when I get a good bed, I like to write about it. This house is pretty good for groups. It would have been nice to have another full-size bathroom but we did ok. The house was very clean. Furniture was comfortable and sufficiently-sized for the number of bedrooms in the home. Parking was good. Supplies were sufficient. We weren’t lacking anything in the kitchen. Sometimes there is left-over oil...
Modern, Spacious, & Convenient 4 BR/3.5 BA Home minutes from golf & shopping
Fridge, microwave, oven, stovetop
Beautiful, Remodeled Penthouse Unit in Old Town!
9.6 out of 10, Exceptional, (7)
"This property is huge for a city apartment. Our family of 5 (two parents, three kids) had plenty of space. The newly updated kitchen is very pretty. It is a short walk to many restaurants and Lincoln Park Zoo. The property manager was very responsive to my questions. We would definitely stay here again."
Beautiful, Remodeled Penthouse Unit in Old Town!
On the beach
Cozy Gary Vacation Rental: Steps to Beach!
9.6 out of 10, Exceptional, (20)
"We enjoyed our stay at this house! There was plenty of beds and the weather was perfect for us to have a bonfire! The wood provided was a little green but burnt well after we got the coals nice and hot. The beach was a quick walk away and a great place to relax and catch some sun. There was plenty of great beach stuff at the house but the umbrella was older and looked broken so we didn't take it. I would rent this house again! If your looking for a place that has a lot of places to eat or things...
Cozy Gary Vacation Rental: Steps to Beach!
Interior
Elegant Mayor's Manor in Central Chicago - 9 Beds
9.6 out of 10, Exceptional, (8)
"Place was as described and worked perfect for our stay."
Elegant Mayor's Manor in Central Chicago - 9 Beds
Beach nearby, sun-loungers
Miller Beach Getaway!
9.6 out of 10, Exceptional, (57)
"From the minute we walked inside we felt right at home! It was very clean and the layout of the house is very welcoming and open. The kitchen had all the necessities to make dinner and enjoy each other with plenty of seating. The hot tub was perfect with the waterfall and lights. It was a short walk to the beach where we enjoyed the day in the sun! We will definitely rent this location again if our travels bring us back up to northern Indiana! This was a mother / daughter weekend to remember."
Miller Beach Getaway!
Outdoor dining
national historic home near downtown airports no parties no events
9.4 out of 10, Exceptional, (19)
"Had a great time used space for birthday event!!"
The price is £278
per night
26 May - 27 May
national historic home near downtown airports no parties no events
Don't see what you're looking for?
See all available properties in South Side
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.

Other property types in South Side

Fridge, microwave, oven, stovetop
LakeHouse
10.0 out of 10, Exceptional, (6)
"I loved this house. It was clean, spacious, the piano made it that much better. I will definitely be back again."
LakeHouse
Fridge, microwave, stovetop, toaster
cozy home in Bridgeport Chicago. walking to park and river front
10.0 out of 10, Exceptional, (1)
"Staying at this VRBO house in Chicago was an absolute knockout! The location was perfect for catching the wrestling show with my friends, and the house itself was spacious, clean, and had all the amenities we needed. From comfy beds to a fully equipped kitchen, we felt right at home. The host was super accommodating and made check-in a breeze. Definitely a five-star experience – would book again in a heartbeat!"
cozy home in Bridgeport Chicago. walking to park and river front
Interior
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, (60)
"The location is perfect for plans to the museums and easy access to Lake Shore Drive. It also has plenty of street parking."
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
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.

South Side Holiday Homes information

Number of reviews
434
Accommodation
191 Holiday Homes
Lowest Price
£251
Highest Price
£278

South Side Hotel Reviews
Expedia verified reviews

Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

5/5 Excellent
"Really great and nice staff! Comfortable beds, clean, and great breakfast options. Great location. Not too touristy but still central. Would highly recommend."
A verified traveller stayed at Embassy Suites by Hilton Chicago Downtown River North
Posted 15 hours ago
Embassy Suites by Hilton Chicago Downtown River North