Northwest Side holiday homes

We found 3,174 holiday rentals — enter your dates for availability

Holiday rentals with weekly discounts – Northwest 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$34,083
for 7 nights, 1 home
NZ$4,869 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 - Northwest Side

Image of Exotic House - Few minutess from O'Hare and Chicago

Exotic House - Few minutess from O'Hare and Chicago

Sleeps 12 · 4 bedrooms · 2 bathrooms
9.4 out of 10
exceptional
(57 reviews)
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Top rated rentals - Northwest Side

Image of Sentral Michigan Avenue

Stay at Sentral

9.0 out of 10
wonderful
(1,414 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 Northwest Side?

The average price for a holiday home in Northwest Side depends on several factors, including season, property type and length of stay. Whether you're searching for a sprawling villa with space for extended family or a cosy cabin perfect for just you and the kids, just enter your travel dates to discover stays with unbeatable value.

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

When you travel and the style and size of the property will influence the cost of your beachside escape. Enter your Northwest Side travel dates to view your available options on Bookabach. Did someone just say "private pool"? Use the filters to pick the amenities and features you want in your holiday home.

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

The minimum required age is normally 16, 18 or 21. It can change from one property to another on Bookabach, so check the rules of your chosen Northwest Side holiday home before booking your escape.

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

The amount of time you can stay in a Northwest Side holiday home for depends on each property. Simply put in your preferred travel dates to browse options that offer long-term stays. They feature everything you need to make your extended trip more convenient and comfortable, like air conditioning and kitchens. Some Bookabach holiday homes may also offer weekly or monthly discounted prices, so you can hang around longer for less.

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