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Holiday Homes in Far Southeast Side

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Check prices for these dates

In two weeks
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

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)
"I had a fun stay "
United States
Jusu K.
The price is AU$294
includes taxes & fees
4 Oct - 5 Oct
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

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

Theater • Game Room • Gym • Firepit • 4BR Home
Belmont Cragin
10.0 out of 10, Exceptional, (6 reviews)
"Great location, safe and quiet. Perfect for our family of 6!"
United States
Jason
The price is AU$820
includes taxes & fees
28 Sept - 29 Sept
Theater • Game Room • Gym • Firepit • 4BR Home
A large, multi-story building with a prominent stone facade and a distinctive triangular roof.

3. A quiet stay while you are away

A quiet stay while you are away
Oak Park
9.8 out of 10, Exceptional, (36 reviews)
"Excellent home! The neighborhood is great and the home has everything you need for a great stay. And if you have any questions, Jay is very good for getting back to you."
United States
Fred D.
The price is AU$407
includes taxes & fees
12 Oct - 13 Oct
A quiet stay while you are away
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 AU$713
includes taxes & fees
25 Sept - 26 Sept
Romantic Escape - Adult Playhouse with Exotic Dungeon

5. Cozy Studio Suite, Steps from River North & Shops

Cozy Studio Suite, Steps from River North & Shops
Near North Side
9.4 out of 10, Exceptional, (3 reviews)
"Clean apartment in cozy neighborhood"
United States
Susannah R.
The price is AU$527
includes taxes & fees
27 Sept - 28 Sept
Cozy Studio Suite, Steps from River North & Shops
A living room with a sectional sofa, a glass coffee table, a fireplace, and a flat-screen TV mounted on the wall.

6. 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, (33 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is AU$426
includes taxes & fees
30 Sept - 1 Oct
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

7. 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 AU$297
includes taxes & fees
25 Oct - 26 Oct
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A modern living room with a sectional sofa, a coffee table, and a TV.

8. Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
8.6 out of 10, Excellent, (4 reviews)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is AU$339
includes taxes & fees
29 Sept - 30 Sept
Attractive Coach House Apartment for rent in Oak Park.
A single-story house with a covered porch, a front door, and a small garden area.

9. Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
Oak Park
10.0 out of 10, Exceptional, (4 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is AU$495
includes taxes & fees
29 Sept - 30 Sept
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard
A white two-story house with a porch, steps, and a small table with chairs.

10. Oak Park Victorian by FLW Studio

Oak Park Victorian by FLW Studio
Oak Park
10.0 out of 10, Exceptional, (33 reviews)
"Would stay there again"
United States
Margaret L.
The price is AU$845
includes taxes & fees
29 Sept - 30 Sept
Oak Park Victorian by FLW Studio
A hotel room with a large bed, two pillows, a teal throw blanket, and a view of buildings through a window.

11. Bronzeville Gem: Balcony, Gym & Rooftop Deck

Bronzeville Gem: Balcony, Gym & Rooftop Deck
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Six of us made a trip to Chicago and stayed at this location. The place is very roomy with a full kitchen. There was public transportation nearby to get us ro everywhere we were going ( Field museum, Grant park, Navy pier)."
United States
Kathy
The price is AU$961
includes taxes & fees
26 Sept - 27 Sept
Bronzeville Gem: Balcony, Gym & Rooftop Deck
A living room with a brick fireplace, a television mounted above it, and a dining area with a table and chairs.

12. 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, (7 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 AU$568
includes taxes & fees
28 Sept - 29 Sept
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A modern kitchen with white cabinets, a central island, stainless steel appliances, and a ceiling fan.

13. Classic Forest Park Foursquare < 1 Mi to Blue Line

Classic Forest Park Foursquare < 1 Mi to Blue Line
Forest Park
10.0 out of 10, Exceptional, (2 reviews)
"Great location, great place to stay, host was friendly. Parking was great. Hoping to be able to stay again in the near future."
United States
LEM R.
The price is AU$664
includes taxes & fees
27 Sept - 28 Sept
Classic Forest Park Foursquare < 1 Mi to Blue Line
A living room with a brown sofa, a coffee table, and a patterned rug. There is a staircase leading to another room.

14. 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, (28 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 AU$632
includes taxes & fees
20 Oct - 21 Oct
Spacious 3br home near Chicago, fenced yard for pets
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, (62 reviews)
"We had a wonderful stay"
United States
Anonymous traveller
The price is AU$515
includes taxes & fees
29 Sept - 30 Sept
LUXE 3 BR, 2 BA + Hot Tub

16. 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 AU$1,030
includes taxes & fees
30 Sept - 1 Oct
Arcade • Theater • Gym • Office • Sleeps 15
A two-story house with a front porch and a small attached garage.

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

Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
Merrilville
6.0 out of 10, (1 review)
"This is not a place to stay with small children; glad mine are grown for this stay. Also, the host really needs to have people they know stay there a bit to see what guests are really looking for. This property really felt like someone is just trying to make money and they don't really care about the people using the property. One of our beds was broken, there were limited furnishings and the tv in the living room was not user friendly at all. I would not recommend this property for any long...
United States
Paula H.
The price is AU$617
includes taxes & fees
4 Oct - 5 Oct
Modern 3BR w/Deck · Minutes from I-65. Fenced Yard
A living room with a flat-screen TV mounted on the wall, a plant on a stand, and a window with blinds.

18. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
The price is AU$993
includes taxes & fees
29 Sept - 30 Sept
4 BR • Theater Room • Gym • Walk to Lincoln Park!
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is AU$451
includes taxes & fees
30 Sept - 1 Oct
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
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

The Chicago Hotel Collection Ambassador Gold Coast

The Chicago Hotel Collection Ambassador Gold Coast

10/10 Excellent
"Much better experience than anticipated based off of reviews. Great location!"
Jade 1-night trip
Posted 1 hour ago
The Chicago Hotel Collection Ambassador Gold Coast

Find out more about Far Southeast Side

Far Southeast Side Holiday Homes information

Number of reviews
208
Accommodation
336 Holiday Homes
Lowest Price
AU$294
Highest Price
AU$1,030

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