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Holiday Homes in Far Southeast Side

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 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

6.6 out of 10, (4)
"Very nice place "
The price is NZ$400
includes taxes & fees
18 Aug - 19 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
Fridge, microwave, oven, stovetop

Charming 2-bedroom house with WiFi in peaceful Hazel Crest

7.4 out of 10, Good, (8)
"The property was very spacious and clean and customer service is very responsive and quick. "
The price is NZ$560
includes taxes & fees
19 Aug - 20 Aug
Charming 2-bedroom house with WiFi in peaceful Hazel Crest
Great 3 bedroom rental unit near Logan Square
Fridge, microwave, oven, stovetop

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.
Fridge, microwave, oven, stovetop

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
Exterior detail

Vintage Urban Retreat

10.0 out of 10, Exceptional, (9)
"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 NZ$825
includes taxes & fees
19 Aug - 20 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

2.0 out of 10, (1)
"When I booked this property it was the intention to have a joyful time with my family for an extended family event. We were unable to access the property the day of causing me to spend an extra 600 for us to stay at another hotel after spending 2 hours on the phone with customer service. To top it off we were harassed by the next door neighbor who attempted to take pictures of our vehicle and report to us that this property was considered an illegal listing. Once we gained entry the property was...
The price is NZ$1,600
includes taxes & fees
19 Aug - 20 Aug
Sleeps 18+, 8BR Kids Room, Game Room, Gym & Theater
Walk to the Beach! Theater-Coffee Bar-Games-Gym
Fridge, microwave, oven, stovetop

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

2.0 star property
9.8 out of 10, Exceptional, (11)
"Everything was as it was described. Very nice "
Walk to the Beach! Theater-Coffee Bar-Games-Gym
LakeHouse
Fridge, microwave, oven, stovetop

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.
Property grounds

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
Fridge, microwave, oven, stovetop

Clarendon Hills Top Floor

6.8 out of 10, (8)
"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.
Fridge, microwave, oven, 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
Terrace/patio

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
Terrace/patio

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

8.8 out of 10, Excellent, (40)
"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
Fridge, microwave, oven, stovetop

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
Fridge, microwave, oven, stovetop

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 NZ$883
includes taxes & fees
8 Sept - 9 Sept
15 mins to beach/Renew+Relax/Clean/ Nat’l Park!/Theater/Game Room/Pet Friendly
4BR Retreat w/ Theater, Game Room & Backyard
Dining

4BR Retreat w/ Theater, Game Room & Backyard

10.0 out of 10, Exceptional, (5)
The price is NZ$919
includes taxes & fees
20 Aug - 21 Aug
4BR Retreat w/ Theater, Game Room & Backyard
13mins from Beach/jet tubs/projector screen/fire place/game rm/exercise rm/
Microwave, oven, stovetop, coffee/tea maker

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

2.0 star property
8.4 out of 10, Very good, (5)
"Host was very nice and communicative! Kindly answered all my questions and made our stay amazing. Thanks! "
The price is NZ$1,105
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
Fridge, microwave, oven, stovetop

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!
Fridge, microwave, oven, stovetop

Lincoln Park Living - Suite 2!

9.4 out of 10, Exceptional, (42)
"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.
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Top Far Southeast Side Hotel Reviews

Congress Plaza Hotel

Congress Plaza Hotel

10/10 Excellent
"We got a king room on the top floor overlooking Buckingham Fountain and Lake Michigan. So pretty. Last night we watched the fireworks show off of Navy Pier. "
Carolyn 1-night trip
Posted 10 hours ago
Congress Plaza Hotel