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Browse Select South Side Cottages

Exterior
Cottage in a Garden
8.0 out of 10, Very good, (1)
"We were visiting daughter and family which was close by. Very cozy place. Host was helpful. The sofa needs to be replaced. The gardens are probably beautiful in the summer. Tv had buffering problems."
Cottage in a Garden
Fridge, microwave, oven, stovetop
Stay near family or close to downtown, this cottage in Beverly has it all!
Stay near family or close to downtown, this cottage in Beverly has it all!
Children’s area
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
9.8 out of 10, Exceptional, (29)
"We booked this cottage for the quirky colors and the loft space we knew our kids would love sleeping in (which they did, of course). What came as a pleasant surprise was the kitchen, equipped with everything you would ever need and more. We brought in two days worth of meals and were absolutely able to make good use of what we brought. We also loved the hammock, the fire pit, the completely charming front yard, and the on site washer and dryer. A great experience and a great location!"
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
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Fridge, coffee/tea maker, cookware/dishes/utensils
Dunland Cottage W/hot tub, paddle boards, fire pit
9.2 out of 10, Wonderful, (15)
"We booked without any issues, but was surprised 100% was due at booking nearly a year in advance. Loved the location/quiet neighborhood, the beds/bedding and hot hub hangout area. Kitchen sink needed some repairs along with the steps from hot tub to back yard. Upon arrival there was only a roll & half of toilet paper for 6 people for 3 nights😞 I also text the day of our arrival to ask if the golf cart was still available to rent & didn’t get a response. We would still stay again because we...
Dunland Cottage W/hot tub, paddle boards, fire pit
Beach nearby
Spacious, Fun and Family Friendly Beach Home
9.8 out of 10, Exceptional, (88)
"We had a great time at the Blue Butterfly. It was a short walk to the beach and a short drive to Mt. Baldy Dunes. Great location. Lots to do. Plenty of room for 3 families. Thank you for a fun stay."
Spacious, Fun and Family Friendly Beach Home
Interior
Cozy Westmont Home: Walk to Metra Station!
3.5 star property
2.0 out of 10, (1)
"Very upset with the communication of this rental. I booked this rental for a weekend getaway with the family. I received an email a couple of days ahead of the booking reminding me of my trip and that I was all set. Then on check in day, I realized that I needed the check in information. I sent a message through the app to the renter. The response was "it may take a few days for the property to get back with you" so I called the number on the response. The operator then tried to look up my...
Cozy Westmont Home: Walk to Metra Station!
Beach
Cozy beach cottage near West Beach.
9.8 out of 10, Exceptional, (10)
"Will rebook"
Cozy beach cottage near West Beach.
Interior
Park Ridge Vacation Rental: 17 Mi to Chicago
3.0 star property
Park Ridge Vacation Rental: 17 Mi to Chicago
Property grounds
“The cottage” 2 bedrooms cozy and private home
9.6 out of 10, Exceptional, (4)
"It was and amazing place me and May family enjoyed it so much."
“The cottage” 2 bedrooms cozy and private home
Interior
Country Club Hills Home w/ Charcoal Grill + Yard!
3.0 star property
Country Club Hills Home w/ Charcoal Grill + Yard!
Interior
Classic Oak Park Home, 11 Mi to Downtown Chicago!
3.5 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Interior
Spacious Family Glenwood Estates Home w/ Hot Tub!
3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!
Exterior
Charming Oak Park Home w/ Private Fire Pit!
3.5 star property
Charming Oak Park Home w/ Private Fire Pit!
Interior
Maywood Vacation Rental w/ Electric Fireplace
3.0 star property
Maywood Vacation Rental w/ Electric Fireplace
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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, oven, stovetop
Cheerful 4 bedroom smart home w/ indoor fireplace
7.4 out of 10, Good, (6)
"The check in process was great and the house was very clean. It was easy to communicate with the property manager. Helped make our trip to chicago great!"
Cheerful 4 bedroom smart home w/ indoor fireplace
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
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 Cottages information

Number of reviews
126
Accommodation
12 Cottages
Lowest Price
Highest Price

South Side Hotel Reviews
Expedia verified reviews