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Holiday Homes in Southwest Side

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Our top choices for Southwest Side holiday homes

ENVITAE Hotel, 4BR Luxury Modern Apartments

ENVITAE Hotel, 4BR Luxury Modern Apartments
Near North Side
9.6 out of 10, Exceptional, (13 reviews)
"Un superbe building avec des prestations sympas, un chouette appartement avec tout ce qu’il faut pour être confortable et les petits détails qui font la différence, notamment pour un court séjour car cela évite de voyager avec ou de courir en acheter: savon pour les mains, shampooing, gel douche, lessive, café etc il est très proche de la ligne rouge du métro et d’un arrêt de bus. "
United States
Emeline B.
The price is €615
includes taxes & fees
8 Jul - 9 Jul
ENVITAE Hotel, 4BR Luxury Modern Apartments

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

Lockport Haven/3 King Beds/Wi-fi/Near Downtown!
Lockport
10.0 out of 10, Exceptional, (9 reviews)
"Amazing property had everything we need! "
United States
Rachel
The price is €406
includes taxes & fees
17 Jun - 18 Jun
Lockport Haven/3 King Beds/Wi-fi/Near Downtown!

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, (27 reviews)
"I had a fun stay "
United States
Jusu K.
The price is €176
includes taxes & fees
16 Jun - 17 Jun
Charming 3-BR home on a cobblestone street near the Lake Michigan waterfront.

Near Lake and Museum • Modern • Game Area

Near Lake and Museum • Modern • Game Area
South Shore
The price is €486
includes taxes & fees
6 Jul - 7 Jul
Near Lake and Museum • Modern • Game Area

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
8.0 out of 10, Very good, (28 reviews)
"Was a very nice stay and the host was very helpful and got very quick responses "
United States
Eduardo
The price is €261
includes taxes & fees
16 Jun - 17 Jun
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi
Worth
9.6 out of 10, Exceptional, (62 reviews)
"Home was exactly what we were needing fir our stay. Host was responsive and timely. "
United States
Stephanie H.
The price is €345
includes taxes & fees
9 Jul - 10 Jul
*The Comfy King Ranch*King Bed Suite*Fast Wi-Fi

✽ Charming Cottage ✽ close to College/Town/Station

✽ Charming Cottage ✽ close to College/Town/Station
Wheaton
10.0 out of 10, Exceptional, (68 reviews)
"This is a cozy little home close to all the things we love about visiting Wheaton. "
United States
Nancy F.
The price is €273
includes taxes & fees
6 Jul - 7 Jul
✽ Charming Cottage ✽ close to College/Town/Station

Attractive Coach House Apartment for rent in Oak Park.

Attractive Coach House Apartment for rent in Oak Park.
Oak Park
10.0 out of 10, Exceptional, (1 review)
"The house was super clean , very quiet neighborhood !! Check in was super easy we enjoyed our stay"
United States
kerston b.
The price is €184
includes taxes & fees
15 Jun - 16 Jun
Attractive Coach House Apartment for rent in Oak Park.

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
10.0 out of 10, Exceptional, (1 review)
"Very welcoming and smells good, cozy feeling to it and quiet neighborhood."
United States
Tomas R.
The price is €212
includes taxes & fees
23 Jun - 24 Jun
Super Sleek large Tiny house by Westmont Metra large enclosed yard and parking.

Entire home in Lockport, Illinois

Entire home in Lockport, Illinois
Lockport
10.0 out of 10, Exceptional, (1 review)
"The house is very clean. The host was very kind and responsive. "
United States
Susan B.
The price is €359
includes taxes & fees
18 Jun - 19 Jun
Entire home in Lockport, Illinois

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
Westchester
9.8 out of 10, Exceptional, (20 reviews)
"Great location and the place was immaculate. Host was very nice."
United States
Carl M.
The price is €590
includes taxes & fees
21 Jun - 22 Jun
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

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

Back Unit Patio, Balcony, Yard, Smart TVs, W/D
Westmont
The price is €301
includes taxes & fees
7 Jul - 8 Jul
Back Unit Patio, Balcony, Yard, Smart TVs, W/D

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, (25 reviews)
"The host was great and communication for her to respond was great. The amenities were good as well"
United States
Shantel U.
The price is €393
includes taxes & fees
22 Jun - 23 Jun
Spacious 3br home near Chicago, fenced yard for pets

Lovely 3-bedroom house in Villa Park with WiFi and AC

Lovely 3-bedroom house in Villa Park with WiFi and AC
Villa Park
9.0 out of 10, Wonderful, (2 reviews)
"Location was great."
United States
Jessica F.
The price is €421
includes taxes & fees
15 Jun - 16 Jun
Lovely 3-bedroom house in Villa Park with WiFi and AC

Cozy Home by O'Hare + EV Plug

Cozy Home by O'Hare + EV Plug
Des Plaines
9.6 out of 10, Exceptional, (11 reviews)
"Beautiful, unique, and clean place to stay. Comfortable beds, quiet, and plenty of space. Great place to stay."
United States
Richie S.
The price is €300
includes taxes & fees
13 Jul - 14 Jul
Cozy Home by O'Hare + EV Plug

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!
Villa Park
8.4 out of 10, Very good, (5 reviews)
"Great location and perfect set up for a family size Vaca!! Loved it!"
United States
Robin C.
The price is €434
includes taxes & fees
15 Jun - 16 Jun
Charming 3BR/2BA Retreat in Villa Park – Comfort, Space & Convenience!

3-bedroom hillside property in woods with fireplace and lake view

3-bedroom hillside property in woods with fireplace and lake view
Lemont
6.0 out of 10, (6 reviews)
"Was very nice to stay owner was very nice it was a pleasant stay for me ,my family and my friends will recommend . "
United States
Jennifer D.
The price is €285
includes taxes & fees
15 Jun - 16 Jun
3-bedroom hillside property in woods with fireplace and lake view

LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub
Elmhurst
8.6 out of 10, Excellent, (50 reviews)
"Great stay"
United States
Steve T.
The price is €321
includes taxes & fees
25 Jun - 26 Jun
LUXE 3 BR, 2 BA + Hot Tub

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, (2 reviews)
"Sweet hosts, beautiful place, and awesome movie/game room. Definitely would stay again."
United States
Willow M.
The price is €327
includes taxes & fees
22 Jun - 23 Jun
Charming 2BR Hideaway FLW District-Theater/Games/Laundry/Office/Private Backyard

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

Game Room • Fire-pit • Playground • Gym • Billiard
Belmont Cragin
The price is €473
includes taxes & fees
9 Jul - 10 Jul
Game Room • Fire-pit • Playground • Gym • Billiard
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 Southwest Side Hotel Reviews

Find out more about Southwest Side

Southwest Side Holiday Homes information

Number of reviews
317
Accommodation
353 Holiday Homes
Lowest Price
€176
Highest Price
€615

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