Holiday Rentals in Orland Park

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Holiday Rentals in Orland Park

Our top choices for Orland Park holiday rentals

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (893)
"great food spots all around and beautiful sites to see "
The price is €170
includes taxes & fees
2 Sept - 3 Sept
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (481)
"It was a great property to stay at, definitely would book again! "
Kasa Magnificent Mile Chicago

Sonder by Marriott Bonvoy Market Hall Apartments West Loop

3.5 star property
8.2 out of 10, Very good, (350)
"Great stay!"
The price is €130
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Market Hall Apartments West Loop

The Neighborhood Hotel-Little Italy

4.0 star property
9.6 out of 10, Exceptional, (193)
"Property was extremely comfortable in a great area."
The Neighborhood Hotel-Little Italy

Sonder by Marriott Bonvoy South Wabash Apartments South Loop

3.5 star property
8.8 out of 10, Excellent, (633)
"Loved this apartment style stay near everything we wanted to visit in Chicago. "
The price is €130
includes taxes & fees
2 Sept - 3 Sept
Sonder by Marriott Bonvoy South Wabash Apartments South Loop

Sonder by Marriott Bonvoy The Burnham Apartments Loop

3.5 star property
9.0 out of 10, Wonderful, (208)
"Great location, room was very nice. Vent in the bathroom wasn’t working and the walls are paper thin so you can hear other people talking loud. Otherwise a great stay! "
The price is €154
includes taxes & fees
14 Sept - 15 Sept
Sonder by Marriott Bonvoy The Burnham Apartments Loop

Kasa South Loop Chicago

4.0 star property
9.4 out of 10, Exceptional, (331)
"Great stay"
Kasa South Loop Chicago

Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

3.5 star property
8.2 out of 10, Very good, (177)
"Great location!!!"
The price is €151
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Jewelers Row Apartments Millenium Park

Sonder by Marriott Bonvoy The Opal Apartments River North

3.5 star property
8.4 out of 10, Very good, (47)
"Great location. Apartment had all the amenities needed. Felt safe. Only not so good part was that being in downtown, it wasn't super quiet at times. Would stay here again without a doubt."
The price is €151
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy The Opal Apartments River North

Comfort Inn Chicago Southland I-80 & I-294 Near Casino

2.5 star property
3.8 out of 10, (52)
"Property is advertised as a Comfort Inn, but is actually undergoing the transformation of becoming a Comfort Inn. It is still very much so operating as a motel on the south side of Chicago. Be safe. "
The price is €82
includes taxes & fees
4 Sept - 5 Sept
Comfort Inn Chicago Southland I-80 & I-294 Near Casino

Kasa River North Chicago

4.0 star property
9.6 out of 10, Exceptional, (165)
"Great location and very clean! Will definitely be staying again. "
Kasa River North Chicago

Sonder by Marriott Bonvoy The Plymouth Apartments Loop

3.5 star property
7.8 out of 10, Good, (132)
"Super convenient location. Lots of parking options and able to walk to all sites in this area."
The price is €132
includes taxes & fees
23 Sept - 24 Sept
Sonder by Marriott Bonvoy The Plymouth Apartments Loop

Cozy Studio in Hyde Park-Walk to Lake & University

10.0 out of 10, Exceptional, (2)
"This place was nice and clean and close to what I needed to do. I appreciated that it was affordable. "
The price is €170
includes taxes & fees
1 Sept - 2 Sept
Cozy Studio in Hyde Park-Walk to Lake & University

Art Villa

5.0 star property
10.0 out of 10, Exceptional, (2)
" "
The price is €1,066
includes taxes & fees
8 Sept - 9 Sept
Art Villa

Stylish 1BR in West Loop

10.0 out of 10, Exceptional, (5)
The price is €190
includes taxes & fees
2 Sept - 3 Sept
Stylish 1BR in West Loop

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Sonder by Marriott Bonvoy Greektown Apartments

3.5 star property
8.6 out of 10, Excellent, (59)
"loved our stay there. close to UIC and Greektown. will stay again"
The price is €221
includes taxes & fees
1 Sept - 2 Sept
Sonder by Marriott Bonvoy Greektown Apartments

Bright & Roomy 4BR in Pilsen

7.8 out of 10, Good, (7)
The price is €263
includes taxes & fees
2 Sept - 3 Sept
Bright & Roomy 4BR in Pilsen

Your Perfect 2BR Home w/ Parking

8.4 out of 10, Very good, (6)
"Our stay was great, the apartment was close to the bus line and the train. The beds were very comfortable and it was a good size for our family. It was nice to have the off street parking in the back although the rear entrance was a bit disheveled. The building was secure but not entirely sound proof, but that is expected in a basement appartment. I would stay here again on a trip to Chicago. "
The price is €225
includes taxes & fees
1 Sept - 2 Sept
Your Perfect 2BR Home w/ Parking

Your Chicago get Away

10.0 out of 10, Exceptional, (2)
"Clean, fun space and responsive host! Loved the views from our room!"
The price is €488
includes taxes & fees
18 Sept - 19 Sept
Your Chicago get Away
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.
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Top Orland Park Hotel Reviews

Find out more about Orland Park

Find out more about Orland Park

Everything you need to know about Orland Park holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Orland Park holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Orland Park holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Orland Park holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Orland Park. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Orland Park holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Orland Park holiday rentals we have selected for you start as low as €82 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Orland Park rentals

At Expedia, we put the best Orland Park holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Orland Park rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Orland Park holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Orland Park. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Orland Park?

Yes, there are holiday rentals in Orland Park close to Centennial Park Aquatic Center, 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 Centennial Park Aquatic Center and Orland Park Sportsplex, whereas Centennial Park is a spot to enjoy the outdoors. Orland Square and Space Golf 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.