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Southwest Side holiday homes

We found 3,011 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Southwest Side

Showing deals for:12 Feb - 19 Feb

Image gallery for Chicago Gold Coast Mansion 6 Bed Luxury Retreat

Interior
10 out of 10, Exceptional, (42 reviews)
Exceptional
(42 reviews)

Chicago Gold Coast Mansion 6 Bed Luxury Retreat

Chicago

7% off
Price is NZ$34,342
for 7 nights, 1 home
NZ$4,906 per night
includes taxes & fees
Chicago Gold Coast Mansion 6 Bed Luxury Retreat

Find spaces that suit your style

Find the best place to stay - Southwest Side

Image of Self-Contained Basement Suite. Separate Entrance. No Shared Indoor Spaces
Premier Host

Self-Contained Basement Suite. Separate Entrance. No Shared Indoor Spaces

Sleeps 2 · 1 bedroom · 1 bathroom
9.8 out of 10
exceptional
(6 reviews)
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Top rated rentals - Southwest Side

Image of Sentral Michigan Avenue

Stay at Sentral

9.0 out of 10
wonderful
(1,415 reviews)
Our late checkin was easy. The room had amazing views of Grant Park/Navy Pier out one window and the city from another window. Apartment was spacious with good facilities. Bed was comfy. Only downside was that the shower had low pressure, but for us that was not a major. Location is really good with most things within walking distance.
N J
Stayed Oct 2024
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  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently Asked Questions

How much does it cost to rent a holiday home in Southwest Side?

A number of factors influence how much you'll pay for a holiday home in Southwest Side, like the season, length of stay and type of property. But, all our holiday homes have something in common — unbeatable value. Just enter your travel dates to find your perfect match.

How much does it cost to rent a beach house in Southwest Side?

The average price for a holiday home near the beach in Southwest Side depends on when you're going and the type and size of property you want. You can easily and quickly find prices on Bookabach by entering your destination and travel dates. Then use the handy filter tool to choose the number of bedrooms and amenities important to you, such as air conditioning, WiFi and a hot tub.

How old do you have to be to rent a holiday home in Southwest Side?

Age restrictions can vary across properties on Bookabach, so double-check the rules of the holiday home in Southwest Side you're considering. But typically, it's 16, 18 or 21.

How long can I rent a holiday home in Southwest Side for?

The amount of time you can rent a Southwest Side holiday home for varies depending on the property. Just tap in your travel dates to find options offering extended stays. They feature all the things you need to make your extended getaway more convenient and enjoyable, like air conditioning and laundries. Some Bookabach holiday homes may also offer discounted weekly or monthly prices, so you can stick around for longer for less.

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