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Holiday Homes in Far Southeast Side

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Far Southeast Side holiday homes

A wooden deck with a railing, a staircase, and a window with a wreath.

1. Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
Robertsdale
9.8 out of 10, Exceptional, (35 reviews)
"Highly recommend this property. It’s located on a quiet clean nice residential street. And the home itself is wonderful: good furnishings, comfortable, three good bedrooms, clean well appointed bathroom, great backyard. I’d stay here anytime I’m in the area."
United States
Ruth Ann G.
The price is NZ$363
includes taxes & fees
21 Oct - 22 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A bedroom with a stone wall, a TV mounted on it, a bed with a white comforter, and a view of the outdoors through a window.

2. Beautifully furnished one bedroom loft located in Chicago's South side suburb

Beautifully furnished one bedroom loft located in Chicago's South side suburb
Hazel Green
10.0 out of 10, Exceptional, (1 review)
"Super great location, we had a concert at Tinley Park, then explored Chicago with a river cruise and Second City Everything was perfect and so eat to just chill, come and go as we pleased In a nice neighborhood and interior was furnished beautifully. Definitely worth the price !!"
United States
Nick L.
The price is NZ$606
includes taxes & fees
18 Oct - 19 Oct
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A hot tub with water, a wooden deck, and a chair.

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

Charming 1-bedroom apt in house by creek with AC, in delightful Portage
Portage
9.8 out of 10, Exceptional, (11 reviews)
"This was a very comfortable space for our Indiana Dunes area trip. It was the perfect place to relax after busy days at the area attractions. Our host was very kind and messaged us after we arrived to make sure we had everything we needed for our stay and again a couple of days later for the same."
United States
Michael T.
The price is NZ$518
includes taxes & fees
31 Oct - 1 Nov
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

4. Romantic Escape - Adult Playhouse with Exotic Dungeon

Romantic Escape - Adult Playhouse with Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (13 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveller
The price is NZ$818
includes taxes & fees
21 Oct - 22 Oct
Romantic Escape - Adult Playhouse with Exotic Dungeon
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

5. Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Westmont
9.4 out of 10, Exceptional, (3 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is NZ$463
includes taxes & fees
9 Nov - 10 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
Thoughtful design touches — from soft textures to greenery and mirrored accents — make this space feel both serene and sophisticated.

6. Theater • Game Room • Gym • Firepit • 4BR Home

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (7 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is NZ$1,417
includes taxes & fees
26 Oct - 27 Oct
Theater • Game Room • Gym • Firepit • 4BR Home
A cozy outdoor hot tub area with a wooden deck, surrounded by a wooden fence and trees.

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

Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
Miller Beach
8.6 out of 10, Excellent, (51 reviews)
"It was a very cute little bungalow and property. We even saw deer!"
United States
Carrah D.
The price is NZ$937
includes taxes & fees
21 Oct - 22 Oct
Secluded, Fenced Cottage, Hot Tub, Fire Pit, Dog Friendly, Nat’l Park
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

8. Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets
Richton Park
9.0 out of 10, Wonderful, (30 reviews)
"Very spacious accommodations in a very nice neighborhood. Convenient to food and shopping. Great value for the cost. "
United States
Greg S.
The price is NZ$799
includes taxes & fees
20 Oct - 21 Oct
Spacious 3br home near Chicago, fenced yard for pets
A modern living room with a sofa, armchairs, a coffee table, a TV, and a large window with curtains.

9. Spacious 3BR · Bronzeville/South Loop · Sleeps 8

Spacious 3BR · Bronzeville/South Loop · Sleeps 8
Near South Side
9.0 out of 10, Wonderful, (6 reviews)
"Excellent stay! The property was clean and an easy walk to McCormick Place convention center. The space was colossal and well appointed, with soap and towels provided for the shower. We were greeted by a wonderful gentleman who took the time to explain the Chicago area to us. Checkout was a breeze—just had to leave our keys—and the instructions were very clear. There was only minimal housekeeping required before leaving the apartment. I would definitely stay here again"
United States
Ilir T.
The price is NZ$1,286
includes taxes & fees
21 Oct - 22 Oct
Spacious 3BR · Bronzeville/South Loop · Sleeps 8
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

10. Back Unit Patio, Balcony, Yard, Smart TVs, W/D

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is NZ$538
includes taxes & fees
19 Oct - 20 Oct
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Room

11. Arcade • Theater • Gym • Office • Sleeps 15

Arcade • Theater • Gym • Office • Sleeps 15
Portage Park
9.0 out of 10, Wonderful, (4 reviews)
"Good place for a large group or family."
United States
Daniel J.
The price is NZ$1,353
includes taxes & fees
18 Oct - 19 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

12. Sleeps 18 • 8BR • Game Room • Gym • Theater

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"The house is beautiful with plenty of space, the park is right across the street, was able to host a birthday party with lots to keep the kids entertained and have space to eat and mingle, the rooms were comfortable and surprisingly large for how small the house looks from the outside. The host responded promptly and was accommodating. Would book and recommend to others!"
United States
Ashley Y.
The price is NZ$1,704
includes taxes & fees
22 Oct - 23 Oct
Sleeps 18 • 8BR • Game Room • Gym • Theater
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

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

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
Maywood
7.8 out of 10, Good, (34 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is NZ$531
includes taxes & fees
21 Oct - 22 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A dining area with a black table set for four, surrounded by chairs. A vase with dried flowers and a candle holder are on the table.

14. 3-bedroom house in lovely Matteson with cool AC breeze

3-bedroom house in lovely Matteson with cool AC breeze
Matteson
10.0 out of 10, Exceptional, (1 review)
"clean, comfortable, hosts very responsive to communications, neighborhood felt safe, perfect location for our stay to attend sectionals NTRP tennis tournament at HF Racquet and Fitness Club"
United States
Susan H.
The price is NZ$1,062
includes taxes & fees
19 Oct - 20 Oct
3-bedroom house in lovely Matteson with cool AC breeze
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

15. LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (64 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is NZ$659
includes taxes & fees
28 Oct - 29 Oct
LUXE 3 BR, 2 BA + Hot Tub
A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

16. Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool

Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
Merrillville
9.8 out of 10, Exceptional, (8 reviews)
"The house was cozy and very clean. The hot tub was amazing! Check-in instructions were clear and easy to follow. The host was very helpful and responsive to messages. We would definitely stay again. Thank you!"
United States
Anonymous traveller
The price is NZ$814
includes taxes & fees
19 Oct - 20 Oct
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A modern kitchen with wooden cabinets, stainless steel appliances, and a white countertop island.

17. Modern 3BR w/Deck · Minutes from I-65. Fenced Yard

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
8.6 out of 10, Excellent, (4 reviews)
"Great pet friendly home and yard. Host was responsive great communication. Excellent, easy to access location."
United States
Lynda L.
The price is NZ$812
includes taxes & fees
16 Nov - 17 Nov
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

18. Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops

Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Lincoln Park
9.6 out of 10, Exceptional, (45 reviews)
"Location was great, beds were comfortable, overall the apartment was well appointed. Unfortunately there was a strong musty smell, mainly in the common areas. We opened the windows and tried running the AC, but couldn’t get rid of it. We did report it to our host, who was going to check it out following our departure."
United States
Alison G.
The price is NZ$1,168
includes taxes & fees
29 Oct - 30 Oct
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
A modern kitchen with grey cabinets, a central island with stools, a microwave, and a dishwasher.

19. An Escape to a Dream of Green and relaxation.

An Escape to a Dream of Green and relaxation.
Miller Beach
9.6 out of 10, Exceptional, (28 reviews)
"Very clean & updated property! The hot tub water looked like it was a fresh refill.We also thoroughly enjoyed how close this property is to the "L TRAIN" stations and the DUNE NATIONAL PARK!!We will be renting this house again for sure!"
United States
Martin R.
The price is NZ$1,046
includes taxes & fees
18 Oct - 19 Oct
An Escape to a Dream of Green and relaxation.
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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