Photo by Deano
Near East Side holiday homes
We found 906 holiday rentals — enter your dates for availability
Discover a selection of 13 apartments and other holiday rentals in Near East Side that are perfect for your trip. Holiday homes offer the amenities that you expect for your stay with friends, family or just your pet, such as parking and a TV. No matter what you're looking for, you're sure to find a property to rent to meet everyone's needs, including a place that's non-smoking or offers accessibility.
Holiday rentals with weekly discounts - Near East Side
Showing deals for:1 Aug - 8 Aug
Image gallery for Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
1010 out of 10 rating
Exceptional
(20 reviews)
Chicago Gold Coast Luxury Home Best Location walking distance to anywhere!
Chicago, IL
8% off
Price is NZ$87,081
NZ$87,081
NZ$12,440 per night
includes taxes & fees
Image gallery for River North 3BR/2BA: HUGE, Parking, Center Chicago
9.89.8 out of 10 rating
Exceptional
(14 reviews)
River North 3BR/2BA: HUGE, Parking, Center Chicago
Chicago, IL
8% off
Price is NZ$14,848
NZ$14,848
NZ$2,121 per night
includes taxes & fees
Image gallery for 3BR Luxury Modern Apartment
9.69.6 out of 10 rating
Exceptional
(7 reviews)
3BR Luxury Modern Apartment
Chicago, Illinois
7% off
Price is NZ$11,811
NZ$11,811
NZ$1,687 per night
includes taxes & fees
Image gallery for City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
1010 out of 10 rating
Exceptional
(27 reviews)
City Center, River North Condo HUGE 3BR, Patio, Parking(2x)
Chicago, IL
12% off
Price is NZ$14,805
NZ$14,805
NZ$2,115 per night
includes taxes & fees
Image gallery for #1613 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(16 reviews)
#1613 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,481
NZ$5,481
NZ$783 per night
includes taxes & fees
Image gallery for #1514 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(10 reviews)
#1514 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,643
NZ$4,643
NZ$663 per night
includes taxes & fees
Image gallery for Spacious,Chic & Steps from MichiganAve|The Hermes
1010 out of 10 rating
Exceptional
(7 reviews)
Spacious,Chic & Steps from MichiganAve|The Hermes
Chicago, Illinois
7% off
Price is NZ$13,231
NZ$13,231
NZ$1,890 per night
includes taxes & fees
Image gallery for Gorgeous 3BR River North Condo - Free Parking
1010 out of 10 rating
Exceptional
(13 reviews)
Gorgeous 3BR River North Condo - Free Parking
Chicago, IL
8% off
Price is NZ$16,006
NZ$16,006
NZ$2,287 per night
includes taxes & fees
Image gallery for Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
9.89.8 out of 10 rating
Exceptional
(32 reviews)
Modern Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
7% off
Price is NZ$9,004
NZ$9,004
NZ$1,286 per night
includes taxes & fees
Image gallery for Spectacular Corner 3BR in the Loop | City Views
8.88.8 out of 10 rating
Excellent
(20 reviews)
Spectacular Corner 3BR in the Loop | City Views
Chicago, Illinois
7% off
Price is NZ$11,794
NZ$11,794
NZ$1,685 per night
includes taxes & fees
Image gallery for #2012 - Kasa Magnificent Mile Chicago
9.49.4 out of 10 rating
Exceptional
(10 reviews)
#2012 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,481
NZ$5,481
NZ$783 per night
includes taxes & fees
Image gallery for #1511 - Kasa Magnificent Mile Chicago
9.69.6 out of 10 rating
Exceptional
(15 reviews)
#1511 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,643
NZ$4,643
NZ$663 per night
includes taxes & fees
Image gallery for #2011 - Kasa Magnificent Mile Chicago
9.89.8 out of 10 rating
Exceptional
(8 reviews)
#2011 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$4,643
NZ$4,643
NZ$663 per night
includes taxes & fees
Image gallery for #1515 - Kasa Magnificent Mile Chicago
1010 out of 10 rating
Exceptional
(23 reviews)
#1515 - Kasa Magnificent Mile Chicago
Chicago, Illinois
8% off
Price is NZ$5,481
NZ$5,481
NZ$783 per night
includes taxes & fees
Image gallery for Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
9.49.4 out of 10 rating
Exceptional
(25 reviews)
Spectacular Penthouse Corner 2BR in Streeterville | Roof Deck | Lake Views
Chicago, Illinois
8% off
Price is NZ$9,642
NZ$9,642
NZ$1,377 per night
includes taxes & fees
Image gallery for Downtown Chicago Studio in Prime Location
9.69.6 out of 10 rating
Exceptional
(9 reviews)
Downtown Chicago Studio in Prime Location
Chicago, Illinois
5% off
Price is NZ$4,765
NZ$4,765
NZ$681 per night
includes taxes & fees
Image gallery for Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
9.89.8 out of 10 rating
Exceptional
(19 reviews)
Amazing & Spacious 3 bed / 2 Bath Townhome Near Downtown, Steps from the train!
Chicago, IL
8% off
Price is NZ$7,351
NZ$7,351
NZ$1,050 per night
includes taxes & fees
Find spaces that suit your style
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Condo/Apartment
Cabin
Cottage
Villa
Chalet
Find the best place to stay - Near East Side
Sonder Onterie
Sleeps 2 · 1 bedroom
8.48.4 out of 10
Very goodvery good
13 reviews(13 reviews)
Group Vacation! 2 Spacious Units Near Oak Street Beach! Onsite Parking!
Sleeps 8 · 2 bedrooms · 2 bathrooms
Steps to Mag Mile, 2 BD, fast Wi-Fi, W&D
Sleeps 4 · 2 bedrooms · 1 bathroom
1010 out of 10
Exceptionalexceptional
3 reviews(3 reviews)
Downtown Guild 4bd/4ba - 2 adjacent 2bds in Gold Coast!
Sleeps 12 · 4 bedrooms · 4 bathrooms
1010 out of 10
Exceptionalexceptional
1 review(1 review)
Sonder Jewelers Row
Sleeps 2 · 1 bedroom
8.48.4 out of 10
Very goodvery good
148 reviews(148 reviews)
Perfect for your Chicago Getaway! Close to Midway Airport! Onsite Parking!
Sleeps 4 · 1 bedroom · 1 bathroom
Peace of mindOur Book with Confidence guarantee gives you 24/7 support
More quality timeFrom booking to staying, the whole process is simple and enjoyable
All the privacy of homeEnjoy full kitchens, laundry, pools, gardens and more
More for lessMore space, more privacy, more amenities — more value
Frequently asked questions
What is the most popular type of holiday home accommodation in Near East Side?
Apartments are the most popular type of holiday home in Near East Side, according to our data. Even if you have a different idea about what you want, Bookabach has properties in many sizes and shapes. Compare our options to find your perfect Near East Side pad.
How much does it cost to rent a holiday home in Near East Side?
A number of factors determine how much you pay for a holiday home in Near East Side, including the time of year, property type and length of stay. But, all Bookabach homes have something in common — unbeatable value. Just enter your travel dates to find your ideal fit.
How much does it cost to rent a beach house in Near East Side?
The average price for a holiday home by the beach in Near East Side will depend on when you’ll be there and the size and style of property you’re looking for. Find prices quickly and easily on Bookabach by entering your dates of travel. Then use our filter tool to pick the number of bedrooms and amenities that you prefer, like a pool, air conditioning and WiFi.
Are there pet-friendly holiday homes in Near East Side?
Pack a travel bag and a bone for your pooch because Near East Side has five holiday homes that throw open their doors to pets. Let your four-legged buddy join in on the family trip at one of our pet-friendly holiday homes on Bookabach. Simply enter your dates and destination, then check our “Pets allowed” filter box.
Can I rent a house with a pool in Near East Side?
Add an extra layer of fun to your getaway by booking one of the five houses with a private pool in Near East Side. Use our search filter to find the kind of property you want on Bookabach, and then spend lazy days splashing and playing in a swimming pool that’s for your exclusive use.
What are popular home amenities in Near East Side?
When it comes to home amenities that people search for in Near East Side, a lake view, a swimming pool and a sauna are at the top of the list. With Bookabach holiday homes, you’ll find options to fit your style and taste, whether you’re holidaying with relatives, friends or even pets.
Are there large group holiday homes in Near East Side?
Take your pick of five Bookabach holiday homes in Near East Side that can accommodate five or more people. You’ll get all the privacy and room you need to have fun with your loved ones — and no one else.
Are there holiday homes in Near East Side that welcome kids?
Gather your entire family for a fun-packed adventure in Near East Side at one of our five family-friendly holiday homes. These stays provide amenities that are just perfect for trips with the kids, like laundry facilities, living rooms and patios. Simply click on the “Properties good for families” filter and pick out your favourite.
What are the top attractions for families in Near East Side?
Keeping the kids amused during your Near East Side holiday is a breeze with these awesome family-friendly attractions:
- Navy Pier
- Chicago Riverwalk
- Shedd Aquarium
Are there holiday homes with WiFi in Near East Side?
Near East Side has five holiday homes with WiFi, so you’ll be able to stay connected while on holiday. Simply check the “WiFi” box in our handy search filter for a list of properties with this feature. From streaming movies with the family to posting pics on social media, these Bookabach homes make it a cinch to get online.
How can I find holiday homes with air conditioning in Near East Side?
You can choose from five Bookabach holiday homes with air conditioning in Near East Side providing that cool, cool breeze and extra bit of comfort. Enter your desired travel dates and then use our handy filters to locate stays with air conditioning.
How old do you have to be to rent a holiday home in Near East Side?
The minimum age is normally 16, 18 or 21. It can change between properties on Bookabach, so look at the rules of your preferred Near East Side holiday home before booking.
How long can I rent a holiday home in Near East Side for?
It’s really down to the Near East Side property. To look at a list of options offering extended stays, simply type your dates and number of people into Bookabach. Enjoy having the place to yourself, as well as amenities such as a fully-equipped kitchen, air conditioning and an outdoor space to run around in. Be on the lookout for any long-term stays that offer discounted weekly or monthly prices.