Oakland, Chicago holiday homes: holiday houses & more

Discover a selection of holiday rentals in Oakland that are perfect for your trip. Holiday rentals provide the best amenities for you and your friends, family or even pets, such as a fireplace and garden. You'll be able to choose a property to rent that has what everyone needs, including places that are non-smoking or accessible.

Holiday rentals with weekly discounts - Oakland

Showing deals for:7 Nov - 14 Nov

Very good

(7 reviews)

Gorgeous N. Kenwood/Hyde Park

Chicago, IL

7% off

NZ$520 per night

includes taxes & fees

Front 1/2 of first floor (old dining table)

Exceptional

(59 reviews)

1 mile walk to 43rd St .beach. In Historic North Kenwood. 6.3 miles to Navy Pier

Chicago, IL

7% off

NZ$751 per night

includes taxes & fees

Exceptional

(86 reviews)

Don't miss out on this one! No cleaning fee. Ideal for McCormick Cntr and U of C

Chicago, IL

8% off

NZ$257 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find the best place to stay - Oakland

Just Minutes from Downtown Chicago

Sleeps 6 · 1 bedroom · 1+ bathroom

Spacious Bronzeville Gem Garden lvl Near Downtown, University of Chicago, Museum

Sleeps 8 · 2 bedrooms · 1 bathroom

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

What is the most popular type of holiday home accommodation in Oakland?

Based on our research, houses are considered the most popular holiday home type in Oakland. But as you'd expect, everyone's idea of an awesome trip isn't the same. Bookabach has holiday homes with every shape, size and budget in mind, so you're bound to find your perfect match.

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

Property type, season and length of stay are some factors that can influence the price of a holiday home. Simply click on your travel dates to find your perfect fit. From cosy country cottages to expansive villas, all Bookabach holiday homes provide unbeatable value.

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

The average price for a holiday home near the beach in Oakland depends on when you're going and the style and size of property you're looking for. Find prices easily on Bookabach by entering your preferred travel dates and destination. Then use the filters to choose the number of bedrooms and amenities essential to you, like WiFi, air conditioning and a hot tub.

What are popular home amenities in Oakland?

A fireplace, a barbecue grill and a garden are rated the most popular home amenities in Oakland. Whether you plan to go as a party of one, with your better half or a group of family members, Bookabach will help you find a holiday home that fits your style with all the features you're looking for.

What are the top attractions for families in Oakland?

Keeping the kiddos entertained during your Oakland holiday is a snap with these cool family-friendly attractions:

Navy Pier
Chicago Riverwalk
Shedd Aquarium

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

The age limit can differ across properties on Bookabach, so be sure to look at the rules of the holiday home in Oakland you're interested in. But in general, it's 16, 18 or 21.

How long can I rent a holiday home in Oakland for?

The amount of time you can stay in an Oakland holiday home for depends on each property. Simply put in your travel dates to see available options that offer long-term stays. They include everything you need to make your extended holiday more convenient and enjoyable, such as air conditioning and laundries. Some holiday homes may also offer discounted weekly or monthly prices, so you can stay longer for less money.