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Douglas Park, Chicago, Cook County, Illinois, United States of America

Douglas Park holiday rentals

We found 1,416 holiday rentals — enter your dates for availability

Discover a selection of 1,500 holiday home rentals in Douglas Park 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 private pool. Prices start at AU$ 156 per night, and holiday houses and flats & apartments are popular options for a stay in Douglas Park. Either way, you'll find holiday accommodation for everyone's needs.
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Find spaces that suit your style

Houses

View 211 Houses

Condos/Apartments

View 1,111 Condos/Apartments

Studios

View 1,024 Studios

Townhouses

View 15 Townhouses

Find the best place to stay — Douglas Park

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

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 1,299 avg/night
(218)

Finest Flat in UIC/Medical District w Parking

Sleeps 5 · 2 Bedrooms · 2 Bathrooms
AU$ 271 avg/night
(66)

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

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 497 avg/night
(129)

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

Sleeps 4 · 1 Bedroom · 1 Bathroom
AU$ 591 avg/night
(333)

Bella Villa onTaylor Street Chicago’s Little Italy 1 mile west the Loop & UIC

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 400 avg/night
(59)

Luxury Home Away From Your Home

Sleeps 8 · 3 Bedrooms · 2 Bathrooms
AU$ 367 avg/night
(41)

Search 1,416 holiday rentals

Top rated rentals — Douglas Park
Stayed Apr 2021

Thank you for great weekend

This property is exactly as shown great location very clean super easy check in and check out. The best stocked rental I have ever stayed in we had everything we needed for a long weekend in Chicago. Bedding was really comfortable. Others mentioned p...

Catherine B.
Catherine B.

Temecula, Ca

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

Cozy Loft

If you are looking for a comfortable studio apartment, very unique in it's style and location this loft is for you. Amy is wonderful in her communication skills, ability to make you feel at home and her flexibility. The apartment has a great location...

john o.
john o.
Stayed Mar 2021

Fun was had by all!

We booked the property to celebrate a birthday with several family members. Communication with the property owners is exceptional from check in to anything you may need. They are very responsive and kind. The property itself is larger than what is s...

Deborah W.
Deborah W.
Stayed Mar 2021

Nice

Very nice property, could use a deep cleaning, I had to clean the bathrooms when we arrived they were not up to par and due to Covid we didn’t want to any chances. Could tell it was a rush job on cleaning and several of the light bulbs were burned ou...

Greg D.
Greg D.
Stayed Mar 2021

Great place, great part of town

As good as the photos! Really appreciated the special touches like the Chicago guest books, tea and coffee, and CDs of fun old movies. In a nice quiet residential area but within just blocks of great shops and restaurants. We would definitely stay he...

Pam P.
Pam P.
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How many holiday accommodation are available around Douglas Park?

Our 2021 accommodation listings offer a large selection of 1,416 holiday rentals around Douglas Park. From 211 holiday houses to 1,111 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 Douglas Park is on Stayz.