Orland Park Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
13 Jan - 14 Jan
Tomorrow
14 Jan - 15 Jan
This weekend
16 Jan - 18 Jan
Next weekend
23 Jan - 25 Jan

Our top choices for Orland Park holiday rentals

Indoor pool
Sentral Michigan Avenue

Sentral Michigan Avenue

Sentral Michigan Avenue
4.0 star property
Downtown Chicago
9.2 out of 10, Wonderful, (1,046 reviews)
"Place was very nice and clean. We enjoyed the stay there. Will book it again when we come back to Chicago visit again. "
United States
Khalid
The price is HK$855
HK$1,232 total
includes taxes & fees
14 Jan - 15 Jan
Sentral Michigan Avenue
Lounge
Kasa River North Chicago

Kasa River North Chicago

Kasa River North Chicago
4.0 star property
Downtown Chicago
9.6 out of 10, Exceptional, (183 reviews)
"Awesome stay "
United States
Sally
Kasa River North Chicago
TV, offices
Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment

Sun-Drenched 1BR Apartment
Downtown Chicago
10.0 out of 10, Exceptional, (2 reviews)
"Host was very friendly and informative. Place was clean and close to lots of fun. Trains loud and busy but knew that going in. "
United States
Tyler B.
The price is HK$491
HK$1,314 total
includes taxes & fees
19 Jan - 20 Jan
Sun-Drenched 1BR Apartment
1 bedroom, WiFi, bed sheets
1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry

1BR Modern Luxe Apt with In-Unit Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"Great experience for me and my wife I would definitely come back "
United States
ShowtimeFam1
The price is HK$491
HK$1,314 total
includes taxes & fees
15 Jan - 16 Jan
1BR Modern Luxe Apt with In-Unit Laundry
Interior
Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space

Twice as Nice: Chic 2BR Stay with Style & Space
Downtown Chicago
9.6 out of 10, Exceptional, (20 reviews)
"The neighborhood was so clean and quiet. Friendly neighbors. Perfect location, not far from everything downtown. "
United States
Shederia P.
The price is HK$538
HK$1,485 total
includes taxes & fees
14 Jan - 15 Jan
Twice as Nice: Chic 2BR Stay with Style & Space
TV, offices
Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry

Modern Comfort: 1BR Unit w/ Laundry
Downtown Chicago
9.8 out of 10, Exceptional, (11 reviews)
"Great host comfortable bed close to restaurants and parks"
United States
Alana C.
The price is HK$491
HK$1,314 total
includes taxes & fees
15 Jan - 16 Jan
Modern Comfort: 1BR Unit w/ Laundry
1 bedroom, iron/ironing board, travel cot, WiFi
West Loop Living – Bright 1BR

West Loop Living – Bright 1BR

West Loop Living – Bright 1BR
Downtown Chicago
10.0 out of 10, Exceptional, (6 reviews)
"Well-outfitted, nice apartment. Nearby (walkable) Jewel-Osco grocery, restaurants, and pay-parking. Moderate noise from nearby Chicago "L" Green Line."
United States
Jeffrey
The price is HK$491
HK$1,314 total
includes taxes & fees
22 Jan - 23 Jan
West Loop Living – Bright 1BR
Interior
River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3

River North Rooftop With In and Out Parking 3
Downtown Chicago
9.6 out of 10, Exceptional, (4 reviews)
"We had a very comfortable stay here. The hosts are exceptionally communicative and helpful. Loved having a place to park my car, and the hosts set it up so my license plate was recognized at the gate so that parking was free. The unit was very clean and spacious. Note, the kitchen does not have pots or pans to cook, so plan on eating out!"
United States
Jennifer M.
The price is HK$780
HK$2,439 total
includes taxes & fees
14 Jan - 15 Jan
River North Rooftop With In and Out Parking 3
TV, offices
Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown

Chicago-Themed 1BR in a Central Spot near Downtown
2.0 star property
Downtown Chicago
The price is HK$491
HK$1,314 total
includes taxes & fees
19 Jan - 20 Jan
Chicago-Themed 1BR in a Central Spot near Downtown
TV, offices
The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home

The One: A 1BR Stay That Feels Like Home
Downtown Chicago
8.4 out of 10, Very good, (5 reviews)
"Very nice condo in a quiet neighborhood"
Canada
Patrick
The price is HK$491
HK$1,314 total
includes taxes & fees
15 Jan - 16 Jan
The One: A 1BR Stay That Feels Like Home
Fridge, microwave, oven, stovetop
Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry

Sleek 1BR Apt w/ Laundry
Downtown Chicago
10.0 out of 10, Exceptional, (1 review)
"I was a little hesitant since I didn’t see any reviews, and was bit nervous. However, all that was put to rest when we arrived. Everything was as described and the photos were accurate. It was clean and minimalistic. Nice space for two for a week. Having the full kitchen was great. About 15 min walk to the brown line and 25 to the blue Line and not a lot of restaurants close by is about the only complaint. Bed could have been more comfortable too."
United States
Anonymous traveller
The price is HK$491
HK$1,314 total
includes taxes & fees
21 Jan - 22 Jan
Sleek 1BR Apt w/ Laundry
Interior
Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown

Stylish Japanese-Themed 2BR Apt Close to Downtown
2.0 star property
Downtown Chicago
The price is HK$538
HK$1,485 total
includes taxes & fees
19 Jan - 20 Jan
Stylish Japanese-Themed 2BR Apt Close to Downtown
TV, offices
Complete 1BR Home Sum

Complete 1BR Home Sum

Complete 1BR Home Sum
Downtown Chicago
The price is HK$491
HK$1,313 total
includes taxes & fees
15 Jan - 16 Jan
Complete 1BR Home Sum
TV
Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt

Sleek & Functional 2-Bedroom Apt
Hyde Park
9.6 out of 10, Exceptional, (4 reviews)
"Nice place for a girls trip weekend. "
United States
Madonna A.
The price is HK$452
HK$1,385 total
includes taxes & fees
20 Jan - 21 Jan
Sleek & Functional 2-Bedroom Apt
Iron/ironing board, travel cot, WiFi, bed sheets
Modern Studio Near UChicago

Modern Studio Near UChicago

Modern Studio Near UChicago
Hyde Park
9.4 out of 10, Exceptional, (12 reviews)
"Clean room and convenient location! "
United States
Gabriela
The price is HK$444
HK$1,181 total
includes taxes & fees
14 Jan - 15 Jan
Modern Studio Near UChicago
TV
Contemporary 2BR Apartment in Vibrant Hyde Park

Contemporary 2BR Apartment in Vibrant Hyde Park

Contemporary 2BR Apartment in Vibrant Hyde Park
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"We stayed in this comfortable, quiet apartment for four weeks when my husband was undergoing radiation treatments for cancer at the University of Chicago Medical Center. It was just what we needed. The location—a block from Lake Michigan with its endless miles of parks and green spaces—was spectacular, and we spent long hours walking our dogs and biking along the lake on the beautifully landscaped walking and biking trails. The apartment itself is well appointed, clean, and blessedly quiet...
United States
Heidi H.
The price is HK$452
HK$1,384 total
includes taxes & fees
15 Jan - 16 Jan
Contemporary 2BR Apartment in Vibrant Hyde Park
Iron/ironing board, travel cot, WiFi, bed sheets
Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location

Studio Unit | Chic + Prime Location
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
"Location was just perfect!"
United States
Meg D.
The price is HK$444
HK$1,181 total
includes taxes & fees
19 Jan - 20 Jan
Studio Unit | Chic + Prime Location
Interior
Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING

Spacious 3-bedroom apartment near downtown, FREE PARKING
Near West Side
9.4 out of 10, Exceptional, (10 reviews)
"Great place to stay that was close to downtown"
United States
Michelle B.
The price is HK$452
HK$2,587 total
includes taxes & fees
2 Feb - 3 Feb
Spacious 3-bedroom apartment near downtown, FREE PARKING
Iron/ironing board, travel cot, WiFi, bed sheets
Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago

Cozy Charm Studio Apt in Chicago
Hyde Park
10.0 out of 10, Exceptional, (2 reviews)
The price is HK$444
HK$1,181 total
includes taxes & fees
14 Jan - 15 Jan
Cozy Charm Studio Apt in Chicago
TV, offices
Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot

Bright 1BR Unit in a Prime Spot
Hyde Park
10.0 out of 10, Exceptional, (1 review)
"We had a great stay. Location is in nice neighborhood with walking access to restaurants and university of Chicago. Apartment was clean and as pictured. Would stay again!!"
United States
christine m.
The price is HK$491
HK$1,314 total
includes taxes & fees
18 Jan - 19 Jan
Bright 1BR Unit in a Prime Spot
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orland Park Hotel Reviews

Holiday Inn Chicago Dwtn - The Mart by IHG

Holiday Inn Chicago Dwtn - The Mart by IHG

10/10 Excellent
"Yes"
Japjeet 2-night trip
Posted 17 hours ago
Holiday Inn Chicago Dwtn - The Mart by IHG

Find out more about Orland Park

Search for holiday rentals in Orland Park on Expedia! You can easily find your home rentals, villas, holiday apartments in Orland Park using one of the methods below:

  • View our selection of featured holiday rentals in Orland Park
  • Use the map to find apartments and other holiday homes in the Orland Park neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Orland Park while they last

Look no further and take a look at our great range of rental properties in Orland Park!

Frequently asked questions

Are there holiday rentals in Orland Park?

Yes, there are holiday rentals in Orland Park close to Orland Park Sportsplex, or you can select a more secluded option if you're looking for a relaxing stay. The shops and restaurants are several reasons why visitors like Orland Park. Make sure you have time to check out the hockey games while you're in the area.

What are some of the best holiday rentals that Orland Park has to offer?

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed: This holiday home rental outside of Orland Park offers a patio, a BBQ and air conditioning to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a stovetop and a microwave.

What’s there to see and do in Orland Park?

Family-friendly attractions include Orland Park Sportsplex and Space Golf, whereas Centennial Park is a spot to enjoy the outdoors. Orland Square and Centennial Park Aquatic Center are other places to visit while you're in town.

What are holiday rentals like in Orland Park?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Orland Park. Holiday rentals feature amenities like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and busy concierge desks while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great choice for family gatherings.