Photo by Marc Jacobs

Holiday Homes in Far Southeast Side

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
15 Aug - 17 Aug
In two weeks
22 Aug - 24 Aug
In one month
5 Sept - 7 Sept
In two months
3 Oct - 5 Oct

Featured Holiday Homes in Far Southeast Side

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Microwave, oven, stovetop, dishwasher

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

6.0 out of 10, (3)
"Very nice place "
The price is AU$363
includes taxes & fees
11 Aug - 12 Aug
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Enjoy cooking in this well-equipped kitchen with a central island, sink, and stainless steel appliances.

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.0 out of 10, Good, (7)
The price is AU$587
includes taxes & fees
18 Aug - 19 Aug
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Great 3 bedroom rental unit near Logan Square
Enjoy cooking in this well-equipped kitchen with a coffee maker and ample countertop space.

Great 3 bedroom rental unit near Logan Square

9.6 out of 10, Exceptional, (51)
"This is a really cute property close to a lot of neighborhood restaurants and bars. The host is really nice and even moved his car for us so we could have his spot when we arrived. We would definitely stay here again. "
Great 3 bedroom rental unit near Logan Square
Cozy Home Sweet Homewood.
Enjoy cooking in this well-equipped kitchen with an oven, gas stove, and dishwasher.

Cozy Home Sweet Homewood.

9.6 out of 10, Exceptional, (32)
"Nice location outside of Chicago, cozy and clean, good communication, would definitely recommend! "
Cozy Home Sweet Homewood.
Vintage Urban Retreat
Sit on the porch and enjoy the serene surroundings.

Vintage Urban Retreat

10.0 out of 10, Exceptional, (8)
"Great house,great location,close to a lot of attractions and bars. Owners was egged to help and responded quickly to all our questions "
The price is AU$870
includes taxes & fees
13 Aug - 14 Aug
Vintage Urban Retreat
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
8 bedrooms, desk, iron/ironing board, travel cot

Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater

The price is AU$1,419
includes taxes & fees
12 Aug - 13 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Enjoy cooking in this well-equipped kitchen with a stainless steel sink, coffee machine, and microwave.

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

2.0 star property
9.6 out of 10, Exceptional, (10)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym
LakeHouse
Kitchen features dark cabinetry, stainless steel appliances, oven, and dishwasher.

LakeHouse

9.2 out of 10, Wonderful, (20)
"Host was perfect an house was perfect!!! It's my second time renting an I will be back again!!"
LakeHouse
Cozy 3-bedroom house in family-oriented Melrose Park.
Stunning single-family home with a backyard surrounded by mature trees and a well-manicured lawn.

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

10.0 out of 10, Exceptional, (20)
"Comfortable beds and room for everyone. Nice quiet neighborhood and a great home away from home. Would stay there again. Host was very easy to work with and responded quickly to questions. "
Cozy 3-bedroom house in family-oriented Melrose Park.
Clarendon Hills Top Floor
Enjoy cooking in this well-equipped kitchen with a stainless steel range hood and a central sink.

Clarendon Hills Top Floor

7.2 out of 10, Good, (7)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
Cheerful 3 bedroom. Feels like home.
Enjoy cooking in this well-equipped kitchen with oven, microwave, and stovetop.

Cheerful 3 bedroom. Feels like home.

3.5 star property
9.8 out of 10, Exceptional, (10)
"It’s a beautiful home, it had everything we needed. It was nice and comfortable!!! Me and my family enjoyed our stay!!!"
Cheerful 3 bedroom. Feels like home.
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Outdoor dining

Charming 1-bedroom apt in house by creek with AC, in delightful Portage

10.0 out of 10, Exceptional, (4)
"Easy check in and wonderful host. Great place to stay near Indiana Dunes and train station to Chicago. "
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Relax in a hot tub on the deck, surrounded by the rustic charm of this cabin.

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park

8.4 out of 10, Very good, (37)
"The yard is awesome, of course the hot tub at the top of the hill was the best, and we enjoyed the firepit as well. The house was a tidy little cottage at which we enjoyed our stay. It’s within a short walk to the National Park and downtown Miller Beach. The neighborhood is fine, pretty secluded, and still close to most attractions."
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
Relax in the hot tub surrounded by comfortable outdoor furniture on the patio.

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

8.8 out of 10, Excellent, (39)
"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"
Huge yard, Family-friendly, Hot Tub, walk to Beach, Dunes, Hiking Trails
New home w/view & party deck - 2nd Floor
Enjoy cooking in this well-equipped kitchen with a large window offering a view of the outdoors.

New home w/view & party deck - 2nd Floor

3.0 star property
10.0 out of 10, Exceptional, (22)
"Great location. Host was accessible and prompt to respond. "
New home w/view & party deck - 2nd Floor
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
Enjoy cooking in this well-lit kitchen with a granite countertop, stainless steel range hood, and white cabinetry.

15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly

8.6 out of 10, Excellent, (13)
"Great place, nice location and the Hosts are extremely good to work with. Highly recommend this just out of the city stay!"
The price is AU$762
includes taxes & fees
13 Aug - 14 Aug
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
4BR Retreat w/ Theater, Game Room & Backyard
Enjoy meals in this dining area with a wooden table, white chairs, and a large mirror.

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (5)
The price is AU$876
includes taxes & fees
25 Aug - 26 Aug
4BR Retreat w/ Theater, Game Room & Backyard
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Enjoy cooking in this well-equipped kitchen with a refrigerator, oven, and stove top.

13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/

2.0 star property
7.4 out of 10, Good, (3)
"The property was beautiful and very modern. There was plenty of space. It had all the amenities to make you feel right at home. It was close to restaurants and casino in Gary. I would definitely stay again!!!!"
The price is AU$1,024
includes taxes & fees
18 Aug - 19 Aug
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Lincoln Park Living - Suite 1
Enjoy cooking in this well-equipped kitchen with a microwave, oven, refrigerator, sink, and coffee maker.

Lincoln Park Living - Suite 1

9.6 out of 10, Exceptional, (30)
"Ideal location and plenty of beds. Communication was easy. My friends and I kept saying how lucky we were to find this place. Highly recommend! "
Lincoln Park Living - Suite 1
Lincoln Park Living - Suite 2!
Enjoy cooking in this well-equipped kitchen with a double sink, oven, and dishwasher.

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (39)
"Great Place. Super area!"
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free