Holiday Homes in Far Southeast Side

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Check prices for these dates

Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov
In one month
11 Dec - 13 Dec
In two months
8 Jan - 10 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, (37 reviews)
"Quiet neighborhood, comfy beds, attentive hosts. Would stay again."
United States
Scott n Holly K.
The price is AU$291
includes taxes & fees
10 Nov - 11 Nov
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.
A bunk bed with a ladder, a small table, a potted plant, and a window with blinds.

2. Vintage meets Modern 20 min from Chicago.

Vintage meets Modern 20 min from Chicago.
Calumet City
The price is AU$521
includes taxes & fees
10 Nov - 11 Nov
Vintage meets Modern 20 min from Chicago.
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.

3. 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 AU$484
includes taxes & fees
10 Nov - 11 Nov
Beautifully furnished one bedroom loft located in Chicago's South side suburb
A spacious living area with a red sofa, beige armchairs, and a glass coffee table. A kitchen is visible in the background with modern appliances.

4. South Loop · 3 Kings · Steps from McCormick Place

South Loop · 3 Kings · Steps from McCormick Place
Near South Side
9.0 out of 10, Wonderful, (10 reviews)
"Great space!"
United States
Kyle H.
The price is AU$813
includes taxes & fees
13 Nov - 14 Nov
South Loop · 3 Kings · Steps from McCormick Place
A bedroom with a bed, a nightstand, a wall-mounted lamp, and a plant.

5. Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon

Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon
South Holland
8.8 out of 10, Excellent, (15 reviews)
"enjoyed my stay cant wait to book again "
United States
Anonymous traveller
The price is AU$650
includes taxes & fees
10 Nov - 11 Nov
Romantic Escape - Adult Playhouse with Red Room & Exotic Dungeon
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

6. Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...

Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
Brookfield
10.0 out of 10, Exceptional, (1 review)
"We enjoyed our stay at Crimson Manor. The property was super clean and well furnished, and kitchen was well-appointed. Stacey was a very responsive and attentive host. Even when we had difficulty getting into the garage, she had it resolved in 10 minutes. The basement game room is awesome - especially if you have a family! We recommend this property!"
United States
Steve H.
The price is AU$639
includes taxes & fees
15 Nov - 16 Nov
Spacious 2BR • Full Basement w/Fireplace • Coffee Bar • Pets OK• Gam...
A marble countertop with a cheese platter, grapes, nuts, and a bottle of wine.

7. Game Room • Fire-pit • Playground • Gym • Billiard

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
9.6 out of 10, Exceptional, (5 reviews)
"Everyone was super happy with the house and the location."
United States
Rhiannon
The price is AU$812
includes taxes & fees
23 Nov - 24 Nov
Game Room • Fire-pit • Playground • Gym • Billiard
A dining table with a bottle of wine, two glasses, a vase with white flowers, and a cheese board with fruits.

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

Sleeps 18 • 8BR • Game Room • Gym • Theater
Portage Park
10.0 out of 10, Exceptional, (10 reviews)
"Wonderful night, boys loved the arcade area."
United States
Anonymous traveller
The price is AU$1,232
includes taxes & fees
10 Nov - 11 Nov
Sleeps 18 • 8BR • Game Room • Gym • Theater
A hot tub with water, a wooden deck, and a chair.

9. 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)
"Nice place close to the beach."
United States
Zdenek M.
The price is AU$373
includes taxes & fees
30 Nov - 1 Dec
Charming 1-bedroom apt in house by creek with AC, in delightful Portage
A modern living room with a grey sofa, a blue bench, and a white door leading to another room.

10. 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
9.6 out of 10, Exceptional, (7 reviews)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is AU$374
includes taxes & fees
11 Nov - 12 Nov
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.
A hotel room with a large bed, dark curtains, a ceiling fan, and a bedside lamp.

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
10.0 out of 10, Exceptional, (1 review)
"Happy with communication, comfort and location"
United States
Kelly K.
The price is AU$416
includes taxes & fees
1 Dec - 2 Dec
Back Unit Patio, Balcony, Yard, Smart TVs, W/D
A modern bathroom with a large mirror, a sink, and two hanging planters with greenery.

12. 4 BR • Theater Room • Gym • Walk to Lincoln Park!

4 BR • Theater Room • Gym • Walk to Lincoln Park!
Lincoln Park
9.0 out of 10, Wonderful, (2 reviews)
"Property is a bit worn, however, furnishings are in good shape and nicely appointed for our stay. Clean upon arrival and great location for an extended stay in Chicago. Host has extra supplies that are helpful- umbrellas, games, laundry detergent that made our stay easier and more enjoyable. Would stay again."
United States
Sara C.
4 BR • Theater Room • Gym • Walk to Lincoln Park!
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, (36 reviews)
"Very nice home with basement bar. Host was very accommodating."
United States
Carl T.
The price is AU$421
includes taxes & fees
16 Nov - 17 Nov
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed
A cozy living room with a neon sign, a fireplace, a television, and a guitar.

14. 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)
"Great location. Great place to stay. "
United States
Jill L.
The price is AU$825
includes taxes & fees
11 Nov - 12 Nov
Lincoln Park Cozy 3bd Home near Zoo | Lake | Shops
Step into a bright, airy space where comfort and style flow seamlessly from the cozy living area into a chic dining room. Whether you're curled up on the sectional with a blanket and coffee or gathering around the modern wood table for a meal with fr

15. 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 AU$824
includes taxes & fees
11 Nov - 12 Nov
Theater • Game Room • Gym • Firepit • 4BR Home
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, (9 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$654
includes taxes & fees
10 Nov - 11 Nov
Couples Getaway - Guesthouse/ In-Law Suite with Jacuzzi/Sauna/Pool
A modern living room with a sofa, coffee table, TV, and a staircase leading to an upper floor.

17. Spacious 5BR 2BA Berwyn Home

Spacious 5BR 2BA Berwyn Home
Berwyn
10.0 out of 10, Exceptional, (1 review)
"experience was good i loved it honestly "
United States
jamya w.
The price is AU$1,008
includes taxes & fees
14 Nov - 15 Nov
Spacious 5BR 2BA Berwyn Home
A covered patio with a hammock, a barbecue grill, and a dining area with a table and chairs.

18. Chicago Riverhouse with private fenced in oasis

Chicago Riverhouse with private fenced in oasis
North Park
10.0 out of 10, Exceptional, (45 reviews)
"House was perfect for our needs and all as described per the listing."
United States
Robert S.
Chicago Riverhouse with private fenced in oasis
A modern living room with a grey sofa, a wooden coffee table, a green sofa, and a large window with curtains.

19. Vibrant House, Walk to Train, Game Room

Vibrant House, Walk to Train, Game Room
Brookfield
10.0 out of 10, Exceptional, (13 reviews)
"Wonderful place to stay!"
United States
Chasity D.
Vibrant House, Walk to Train, Game Room
A dining area with a glass-top table, beige upholstered chairs, a patterned rug, and a chandelier.

20. 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 AU$509
includes taxes & fees
16 Nov - 17 Nov
LUXE 3 BR, 2 BA + Hot Tub
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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Learn more about Far Southeast Side

Discover things to see and do in Far Southeast Side as you venture to popular sights like Lake Michigan.

See all hotels in Far Southeast Side
A man standing on a rocky outcrop with a large concrete structure in the background.

Top reviews in Far Southeast Side

An outdoor seating area with tables and chairs, a planter with greenery, and a large brick structure in the background.
Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton

Sable at Navy Pier Chicago, Curio Collection by Hilton
Downtown Chicago

10/10 Excellent

This was nice and convenient. Perfect area and everything was closed by.
Australia
Jezreel Elaine
Reviewed May 17, 2024
Sable at Navy Pier Chicago, Curio Collection by Hilton

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