Photo by Marc Jacobs

Search Far Southeast Side Cottage Rentals

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Browse Select Far Southeast Side Cottages

Dunland Cottage W/hot tub, paddle boards, fire pit

8.2 out of 10, Very good, (20)
"Stayed in Naomi’s home for a weekend with some friends visiting from out of town! We had a great time and was pleased with the home + it was very comfortable and easy to drive to the beach. The paddleboards and beach chairs that came included for our use were awesome! There were some small issues - one of the bedrooms had a duvet that unfortunately smelled and we had to remove it, and while we were staying we experienced issues with the hot tub that were not resolved by the time our stay ended,...
Dunland Cottage W/hot tub, paddle boards, fire pit

Pet-friendly Lake Getaway: 1 Block to Beach!

3.0 star property
Pet-friendly Lake Getaway: 1 Block to Beach!

Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

10.0 out of 10, Exceptional, (33)
"Very clean, fun, festive place to stay. Plenty of beds for our family of seven. And more space than expected for us all to spread out and do our own thing if we wanted to. Extremely impressed with the communication and accomodations made for us while staying from the Host, Robin. Thank you so much for everything. It was a great weekend away. Kids had a great time at the cottage as well as at the beach which is so close you can hear the waves from the screened in porch which was awesome!! "
Fun w/Loft! Beach ~Nature Trails ~Grill~ Firepit ~Indiana Dunes National Park

Spacious, Fun and Family Friendly Beach Home

9.8 out of 10, Exceptional, (93)
"I grew up nearby and knew some of Gary is rundown, but this was not the case here in Miller Beach. The neighborhood is older and the property next door is abandoned, but THIS property is well-maintained, the host was very responsive, and it's 2 blocks from the water. We had a great time at the beach, exploring the dunes, and even just hanging out watching some TV. "
Spacious, Fun and Family Friendly Beach Home

Cozy Westmont Home: Walk to Metra Station!

3.0 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!

Cozy beach cottage near West Beach.

8.4 out of 10, Very good, (13)
"The host was communicative and amenable to a late check out which was appreciated. The property was a good size and there was even a pool that we did not expect, or use as it wasn’t fully functional. But most of all it was not very clean, we went through and wiped all the surfaces, the bed we used had dirty sheets, and none of the outdoor furnishings had been cleaned. We purchased and replaced the kitchen and bathroom rugs and the kitchen did not have a good set up of utensils, etc. We use...
Cozy beach cottage near West Beach.

“The cottage” 2 bedrooms cozy and private home

9.6 out of 10, Exceptional, (5)
"6 girls in one house, everyone had a bed or couch to sleep on, clean and convenient "
“The cottage” 2 bedrooms cozy and private home

Country Club Hills Home: Walk to Rec Center!

3.0 star property
Country Club Hills Home: Walk to Rec Center!

Classic Oak Park Home, 11 Mi to Downtown Chicago!

3.0 star property
Classic Oak Park Home, 11 Mi to Downtown Chicago!

Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

3.0 star property
10.0 out of 10, Exceptional, (1)
"So cozy. Feels like staying in a guest house with the whole place to yourself! "
Oak Park Home w/ Fire Pit - 5 Mi to Garfield Park!

Gary Cottage w/ Outdoor Dining Areas - Near Beach!

8.8 out of 10, Excellent, (6)
"Very clean, nice, and accomidating"
Gary Cottage w/ Outdoor Dining Areas - Near Beach!

Steps to Lake Michigan Beach: Gary Vacation Rental

3.0 star property
Steps to Lake Michigan Beach: Gary Vacation Rental

Charming Crete Home w/ Hot Tub, Deck & Fire Pit

3.0 star property
Charming Crete Home w/ Hot Tub, Deck & Fire Pit

Gary Cottage w/ Outdoor Dining Areas - Near Beach!

3.0 star property
Gary Cottage w/ Outdoor Dining Areas - Near Beach!

Spacious Family Glenwood Estates Home w/ Hot Tub!

3.0 star property
Spacious Family Glenwood Estates Home w/ Hot Tub!

13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

3.0 star property
13 Mi to Dtwn Chicago: Maywood Home w/ Fireplace

Homewood Home ~ 1 Mi to Metra Station!

3.0 star property
Homewood Home ~ 1 Mi to Metra Station!

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

3.0 star property
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

Renovated Griffith Family Home in Chicagoland Area

3.0 star property
Renovated Griffith Family Home in Chicagoland Area

Gary Vacation Rental < 1 Mi to Indiana Dunes NP!

3.0 star property
Gary Vacation Rental < 1 Mi to Indiana Dunes NP!
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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Other property types in Far Southeast Side

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (592)
"We stayed stayed at the Sentral for a business/family trip. This hotel is beautiful and accommodating. Sandra at the front desk was the sweetest and made check in a breeze, even allowing us to check in early. The room was clean, however there was a burn mark on the kitchen floor and it appeared as it was not vacuumed. Otherwise the room was wonderful, we would definitely stay here again! "
The price is CA $151
CA $218 total
includes taxes & fees
Nov 24 - Nov 25
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (208)
"Easiest check in and check out process "
The price is CA $79
CA $92 total
includes taxes & fees
Dec 22 - Dec 23
Sonder Market Hall

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (395)
"Nice"
The price is CA $169
CA $198 total
includes taxes & fees
Dec 19 - Dec 20
Sonder South Wabash
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.
Beautiful view of the beach with palm trees

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