Near North Side holiday homes

We found 1,165 holiday rentals — enter your dates for availability

Discover a selection of 506 apartments, 29 flats and other holiday rentals in Near North Side that are perfect for your trip. Holiday rentals provide the best amenities for your stay with friends, family or just your pet, such as Wi-Fi and a pool. You'll be able to choose a property to rent for everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts - Near North Side

Showing deals for:13 Feb - 20 Feb

Image gallery for Luxury 2BR on Michigan Ave with Private Balcony

Living area
9.8 out of 10, Exceptional, (16 reviews)
Exceptional
(16 reviews)

Luxury 2BR on Michigan Ave with Private Balcony

Chicago, IL

7% off
Price is NZ$5,261
for 7 nights, 1 apartment
NZ$752 per night
includes taxes & fees
Luxury 2BR on Michigan Ave with Private Balcony

Image gallery for 2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome

Living area
8.2 out of 10, Very good, (15 reviews)
Very good
(15 reviews)

2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome

Chicago, IL

10% off
Price is NZ$3,942
for 7 nights, 1 home
NZ$563 per night
includes taxes & fees
2 Rooftops, 2 Car Garage, 4 Stories|Down-Townhome

Image gallery for River North's Rock N' Roll - In The Heart of the City

River North Luxury Living
9.6 out of 10, Exceptional, (92 reviews)
Exceptional
(92 reviews)

River North's Rock N' Roll - In The Heart of the City

Chicago, IL

7% off
Price is NZ$5,784
for 7 nights, 1 apartment
NZ$826 per night
includes taxes & fees
River North's Rock N' Roll - In The Heart of the City

Image gallery for Historic Charm + Modern Comfort for Tourists

Living area
10 out of 10, Exceptional, (7 reviews)
Exceptional
(7 reviews)

Historic Charm + Modern Comfort for Tourists

Chicago, IL

7% off
Price is NZ$4,913
for 7 nights, 1 apartment
NZ$702 per night
includes taxes & fees
Historic Charm + Modern Comfort for Tourists

Find spaces that suit your style

  • 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 Near North Side?
Apartments are the most popular style of holiday home in Near North Side, according to our data. Even if you have something different in mind, Bookabach has properties in all sizes and shapes. Explore our options to find your perfect match.
How much does it cost to rent a holiday home in Near North Side?
Length of stay, property type and time of year are some factors that can determine the price of a holiday home. Simply enter your dates of travel to find your ideal fit. From cosy chalets to sprawling luxury villas, all Bookabach holiday homes offer incredible value.
How much does it cost to rent a beach house in Near North Side?
Prices for beach houses in Near North Side can vary depending on the size and style of the property and time of year you're travelling. Just enter your travel dates into Bookabach and how many guests to view available options and prices. From there you can use our filter tool to narrow your search by ratings, nearby activities, amenities and more.
Are there pet-friendly holiday homes in Near North Side?
Yes, there are. You'll have your pick of 429 holiday homes that cater to pets in Near North Side. Some of our pet-friendly holiday homes come with an outdoor space for your fur child to run around in, complimentary treats, doggie beds and proximity to parks. Apply the "Pets allowed" filter to find your pawfect place on Bookabach.
Can I rent a house with a pool in Near North Side?
Add a whole other level of fun to your getaway by staying in one of the 103 houses with a private pool in Near North Side. Use our search filter to find properties with pools on Bookabach, then spend your downtime frolicking in a swimming pool that's all your own.
What are popular home amenities in Near North Side?
A lake view, a fireplace and a water view are rated the most popular home amenities in Near North Side. Whether you're heading away on your own, with your sweetheart or as a family group, Bookabach can help you find a holiday home that matches your tastes with all the extras you're looking for.
Are there large group holiday homes in Near North Side?
With 42 holiday homes that can host 10 guests or more in Near North Side, there's no need to cross anyone off the invite list. From extended family holidays to special events like Christmas and birthday parties, Bookabach will help you find a large group home to suit the occasion.
Are there holiday homes in Near North Side that welcome kids?
With 428 family-friendly holiday properties to choose from in Near North Side, now is an awesome time to introduce the kiddos to the wonders of travel. Simply check our "Properties good for families" filter box to search for stays loaded with amenities perfect for travelling families, such as dining rooms, backyards, hot tubs and entertainment areas.
What are the top attractions for families in Near North Side?
Keep your kids occupied at these top family-friendly attractions in Near North Side:

  • Navy Pier
  • Chicago Riverwalk
  • Shedd Aquarium

Are there one-bedroom holiday homes in Near North Side?
Yes, there are 169 one-bedroom properties in Near North Side to pick from. A one-bedroom holiday home is a great choice if it's just the two of you or if you're travelling solo. Throw in more privacy, convenience and space compared to a standard hotel, and you're sure to have a break to remember.
Can I find two-bedroom holiday homes in Near North Side?
Near North Side has 100 two-bedroom holiday properties for you to select from. Experience a holiday home with all the privacy and comfort you're looking for at a fantastic price on Bookabach.
Are there holiday homes with WiFi in Near North Side?
Near North Side has 64 holiday homes with WiFi, so you can stay connected while travelling. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with the family to updating your social media, these Bookabach homes make it easy to go online.
How can I find holiday homes with air conditioning in Near North Side?
Pick your travel dates and then make use of the filters to locate holiday homes with ac in Near North Side on Bookabach. With 418 air-conditioned properties to choose from here, you can enjoy a cool and comfortable stay.
How old do you have to be to rent a holiday home in Near North Side?
You should check with the Near North Side holiday home you'd like on Bookabach as age restrictions differ. However, it's typically 16, 18 or 21.
How long can I rent a holiday home in Near North Side for?
How long you can book a holiday home in Near North Side is up to the property. Simply enter your chosen travel dates to display a list of options offering extended stays. With loads of creature comforts such as laundries and air conditioning, as well as some offering weekly or monthly discounts, you're sure to discover a terrific place to call your home away from home in Near North Side.

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