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Search Holiday Homes in Far Southeast Side

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Browse Select Far Southeast Side Holiday Homes

Stylish 3bd w/ backyard patio mins from Downtown!

2.0 star property
8.8 out of 10, Excellent, (3)
"Very comfortable home. Location was great. Owners were very responsive and helpful. A storm on our last day unfortunately left us without power, owner was great at keeping us informed of status. Already went to book for our next trip but someone beat us to it. "
Stylish 3bd w/ backyard patio mins from Downtown!

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (16)
"This is a great place and very pet friendly. Only negatives were lack of hashtags (only one in the home), no hair dryer when it advertised it had one, and no TV in any of the bedrooms. The home was clean, spacious, fireplace and hot tub are a great bonus."
Cozy 3-bedroom house in family-oriented Melrose Park.

Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

8.8 out of 10, Excellent, (37)
"We had a great stay! The property was perfect- hot tub, plenty of beds, comfortable beds, walking distance to Lake Michigan! Home was comfortable and clean and the managers were easy to reach with questions-just a text away. Would definitely stay here again"
The price is £588
includes taxes & fees
10 Jul - 11 Jul
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails

Great 3 bedroom rental unit near Logan Square

9.4 out of 10, Exceptional, (42)
"Safe neighborhood and super responsive host. I would definitely book again."
Great 3 bedroom rental unit near Logan Square

Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

10.0 out of 10, Exceptional, (11)
"Lots of good food and close to transit! Amazing little spot."
Hermosa House ECO-HOME - Quiet, Peaceful 3BR + Free Parking by Logan Square

Charming 3-bedroom house with WiFi in peaceful Hazel Crest

8.0 out of 10, Very good, (4)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is £275
includes taxes & fees
7 Jul - 8 Jul
Charming 3-bedroom house with WiFi in peaceful Hazel Crest

Belmont House, Classy & Chic/walk to Wrigley Field

9.4 out of 10, Exceptional, (43)
"The place was located right down the street from where the concert was at. Cute place, better than a hotel, parking right outside the place. "
Belmont House, Classy & Chic/walk to Wrigley Field

Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

4.0 star property
9.4 out of 10, Exceptional, (40)
"Numerous problems that owner tried to fix-no wi-fi, no ac, broken upstairs dishwasher, basement flooded when we used downstairs washing machine. Place had not been cleaned prior to check in, trash sack in entry way, litter on floor, mop on back steps. Great location."
Huge Wrigleyville Beauty -10 beds and 5 baths in the heart of it all!!

Lincoln Park Living - Suite 1

9.4 out of 10, Exceptional, (26)
"Great location in a beautiful part of town. Walk to Wrigley. Place was great for 2 families to hang out. "
Lincoln Park Living - Suite 1

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.6 out of 10, Exceptional, (7)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym

Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

2.0 out of 10, (1)
"Here is a condensed version of the document, aiming for around 1500 characters:Review of rental: Communication was good, but the house was problematic. It looked abandoned with overgrown shrubs and a "Beware of Dog" sign. Jessica, the host, was finishing cleaning upon arrival due to a late checkout. The living room had an 85" TV but only one lamp with no shade. One couch was broken. The dining room had a table and a makeshift hutch. The kitchen was odd with mismatched items; no coffee pot for...
Relaxing hot and beautiful 4 bed, 2 baths in peaceful area

The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

9.6 out of 10, Exceptional, (166)
"Great location. Has everything we needed. Great host. Have already recommended it to others who visit Chicago frequently and will definitely stay there again. "
The Original Wrigleyville Coach House- 2 Story, Private, Single Family Residence

Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

10.0 out of 10, Exceptional, (2)
"The area is quiet and the apartment is close to a dog park which is open to non-residents. There is a paved walkway right by the park that’s nice so I was able to walk my dog in the morning. The property manager immediately replied to any questions I had and the apartment was fully stocked in the kitchen, etc. I booked this because of the cost. I was in town to see the Indiana Dunes. I would stay here again."
The price is £123
includes taxes & fees
6 Jul - 7 Jul
Charming 1-bedroom townhome with WiFi, AC in enjoyable Thornton

Miller Beach and Indiana Dunes National Park Vacation House

10.0 out of 10, Exceptional, (35)
"The place was exactly what we wanted for the few days we stayed. Close to the beach and Lake Michigan."
Miller Beach and Indiana Dunes National Park Vacation House

Relaxing Oak Park Home

9.8 out of 10, Exceptional, (79)
"Kitchen, dining room, living room, bathroom, and bedrooms were all spacious and well-appointed. Beds were comfortable. House was warm and cozy. "
Relaxing Oak Park Home

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

8.0 out of 10, Very good, (5)
"The space - number of rooms and bathrooms - was great for a big group. We were able to sleep multiple families comfortably with no issues getting ready with the number of bathrooms. There was plenty of free street parking close, so we also didn't have any problems finding parking for all our cars. Some more specific instructions on how to use the key pad (to enter and lock) would be helpful, but otherwise no complaints! I would recommend this Vrbo! "
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Pet-Friendly Lake Getaway: 1 Block to Beach!

10.0 out of 10, Exceptional, (38)
"Great location. Home is very clean. Enjoyed our stay."
Pet-Friendly Lake Getaway: 1 Block to Beach!

Quiet Stay - Perfect for Family

Quiet Stay - Perfect for Family

Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

10.0 out of 10, Exceptional, (169)
"Great place for our large group. Lots of room for the bridal girls to get ready for the wedding. "
Lincoln Park Single Family Home (4bdrm 3.5 bth)-2 Car Garage 4200sqft Sleeps 24

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (33)
"Great space, good location. Very easy check out process."
Lincoln Park Living - Suite 2!
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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