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Near East Side holiday rentals

We found 432 holiday rentals — enter your dates for availability

Discover a selection of 432 holiday home rentals in Near East Side that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Stayz holiday homes have the best amenities for hanging out with the people that matter most, including pool and internet/WiFi. Prices start at AU$ 108 per night, and holiday houses and flats & apartments are popular options for a stay in Near East Side. Either way, you'll find holiday accommodation for everyone's needs.
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Find spaces that suit your style

Houses

View 35 Houses

Condos/Apartments

View 395 Condos/Apartments

Studios

View 355 Studios

Find the best place to stay — Near East Side

Luxury Downtown Chicago Apartment with Panoramic Views of Lake Michigan

Sleeps 4 · 2 Bedrooms · 2 Bathrooms
AU$ 522 avg/night

**WOW**1bd/1ba Condo in Heart of City!!

Sleeps 3 · 1 Bedroom · 1 Bathroom
AU$ 587 avg/night
(2)

19th Floor Condo Located in the Heart of the City!

Sleeps 3 · 1 Bedroom · 1 Bathroom
AU$ 540 avg/night
(1)

55/56th Floor Penthouse - VIEWS, Fireplace, Balcony, Fitness Center

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 1,592 avg/night
(218)

51st Floor MagMile Penthouse - VIEWS, Fireplace, Balcony, Pool, WiFi

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 545 avg/night
(130)

52nd Floor MagMile Penthouse - VIEWS, Fireplace, Fitness Center, Pool, WiFi

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 584 avg/night
(332)

Search 432 holiday rentals

Top rated rentals — Near East Side
Stayed Apr 2021

Love the Penthouse

The property is Awesome. A great balcony to stand and watch the city. The penthouse is well appointed, tasteful art, and all the things you need if you want to cook. Grand station off the red line is right there as well as a market. Uber was always a...

Jim A.
Jim A.

California, USA

Stayed Mar 2021

A Million Dollar View

WOW! What a beautiful place with views that are priceless! Everything was just as pictured and described and couldn’t be happier with our decision to stay there. Nicely equipped, great location, and so nice to stay in a place that was so spacious and...

Debra G.
Debra G.
Stayed Mar 2021

Beautiful condo stay

This property was a highlight of our trip to Chicago. It is conveniently located to restaurants, activities, and a very convenient grocery attached at the street level. But it’s real value is it’s outstanding skyline views while relaxing in a very co...

Lewie S.
Lewie S.
Stayed Mar 2021

Amazing views and perfect location

We came to Chicago for a short break and really enjoyed our stay. The property was just as described, and so comfortable, too. The views were incredible, from the sunrise over the lake at dawn to the beautiful city lights at night! The location was p...

Julie S.
Julie S.
Stayed Mar 2021

Perfect location. Beautiful townhouse

We were looking for a quiet home where we could relax in the middle of the city and this townhouse was perfect. It’s very spacious, beautiful and comfortable. The location couldn’t be better. It’s close to everything including the MCA. The owners pro...

Park-Egli F.
Park-Egli F.

Nashville

Stayed Mar 2021

Absolutely delightful stay

Lovely views from the 52nd floor of a great building. The condo is spacious and clean and looked better than the photos! Close to everything we wanted to see, do and eat for our 4 day visit. I had forgotten a couple of print outs but on the 9th floor...

Janice C.
Janice C.
Stayed Feb 2021

A different four walls

Got away to this property as a way of being in a different four walls during the pandemic (and, as it happens, a generational snowstorm). Everything was as it was described. The property manager was very responsive and accommodating. Would be great f...

Frank H.
Frank H.
Stayed Jan 2021

Great Downtown Stay!

We really enjoyed our week in the sky in downtown Chicago. While we are from this area, we have never had a chance to enjoy the city from this height or location. We explored the neighborhood, and the building! The building amenities were excellent, ...

Suzanne M.
Suzanne M.
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How many holiday accommodation are available around Near East Side?

Our 2021 accommodation listings offer a large selection of 432 holiday rentals around Near East Side. From 35 holiday houses to 395 flats & apartments, find unique holiday homes for you to enjoy a memorable holiday or a weekend with your family and friends. The best place to stay around Near East Side is on Stayz.