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Compare 14 Cottages in South Side with updated reviews, rates, and availability.

Cozy beach cottage near West Beach.
9.8 out of 10, Exceptional, 10 reviews
"Will rebook"
Cozy beach cottage near West Beach.
Stay near family or close to downtown, this cottage in Beverly has it all!
10.0 out of 10, Exceptional, 2 reviews
"Great Stay!"
Stay near family or close to downtown, this cottage in Beverly has it all!
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
9.8 out of 10, Exceptional, 30 reviews
"Our fam of five 6, 8 and 12 year olds LOVED our quiet little getaway. We knew the water would be a bit chilly on Lake Michigan but boy was it beautiful...and only a few blocks away! Our kiddos slept in loft. We made every meal there, hiked some trails, played some of the games there and some we brought. There were plenty towels, bath and beach as well as kitchen accessories. It was a perfect getaway before our busy theatre rehearsals and sports camps begin! We definitely hope to come back!"
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park
Dunland Cottage W/hot tub, paddle boards, fire pit
9.2 out of 10, Wonderful, 15 reviews
"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
Spacious, Fun and Family Friendly Beach Home
9.8 out of 10, Exceptional, 88 reviews
"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
Cozy Westmont Home: Walk to Metra Station!
3.5 star property
2.0 out of 10, 1 review
"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!
Park Ridge Vacation Rental: 17 Mi to Chicago
3.0 star property
Park Ridge Vacation Rental: 17 Mi to Chicago
“The cottage” 2 bedrooms cozy and private home
9.6 out of 10, Exceptional, 4 reviews
"It was and amazing place me and May family enjoyed it so much."
“The cottage” 2 bedrooms cozy and private home
Cottage in a Garden
9.0 out of 10, Wonderful, 2 reviews
"Great place to stay, quiet, with privacy sorounding by beautiful garden "
Cottage in a Garden
Country Club Hills Home w/ Charcoal Grill + Yard!
3.0 star property
Country Club Hills Home w/ Charcoal Grill + Yard!
Classic Oak Park Home, 11 Mi to Downtown Chicago!
3.5 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Spacious Family Glenwood Estates Home w/ Hot Tub!
3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!
Charming Oak Park Home w/ Private Fire Pit!
3.5 star property
Charming Oak Park Home w/ Private Fire Pit!
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

LakeHouse
10.0 out of 10, Exceptional, 7 reviews
"Great"
LakeHouse
cozy home in Bridgeport Chicago. walking to park and river front
10.0 out of 10, Exceptional, 1 review
"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
Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum
9.8 out of 10, Exceptional, 60 reviews
"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 Cottages information

Number of reviews
130
Accommodation
14 Cottages
Lowest Price
Highest Price

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