Search Vacation Homes in Orland Park

    Plan, book, stay with confidence
    bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Compare 465 Vacation Homes in Orland Park with updated reviews, rates, and availability.

Stunning Duplex Condo #1 - Downtown River North
10.0 out of 10, Exceptional, (2)
"This location was incredible and it was perfect for what we needed to do. We were in town for NEOCON/Design Days and this was a wonderful home base for us. It was walking distance to almost everything, and right by the CTA station as well. Starbucks was also close which was nice."
Stunning Duplex Condo #1 - Downtown River North
Luxury Home Away From Your Home
9.0 out of 10, Wonderful, (107)
"The place was nice and clean but missing some basic items such as floor mats and decent pans, otherwise our stay was good. It was near all the places we need to go"
Luxury Home Away From Your Home
Luxury Downtown Penthouse with Private Rooftop!
10.0 out of 10, Exceptional, (5)
"This was exactly what we were looking for! Great location and will stay anytime I’m in Chicago!"
Luxury Downtown Penthouse with Private Rooftop!
Save an average of 15% on thousands of hotels when you're signed in
Chic 3bed 2bath Home with free parking close to United Center
10.0 out of 10, Exceptional, (5)
"Great place to stay. Very clean, pretty home. Would stay there again. Great hostess."
The price is SAR 938
SAR 1,618 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Chic 3bed 2bath Home with free parking close to United Center
national historic home near downtown airports no parties no events
9.0 out of 10, Wonderful, (21)
"It was an amazing property so quiet and calm area lovely host super great with communication and answering any questions I had"
The price is SAR 1,126
SAR 1,296 total
includes taxes & fees
17 Jum. II - 18 Jum. II
national historic home near downtown airports no parties no events
Breathtaking Downtown Penthouse B - Sleeps 11
10.0 out of 10, Exceptional, (4)
"The unit was a great size for our 7-person group trip to Chicago. We’ll appointed with pulsated hardware and decor. Super close to transit made getting to Wrigley, Navy Pier, Downtown, and the zoo extremely easy. Rooftop was a amazing and Dan was responsive and made the check in/out process a breeze."
Breathtaking Downtown Penthouse B - Sleeps 11
Breathtaking Downtown Penthouse A - Sleeps 11!
9.4 out of 10, Exceptional, (3)
"We stayed here with 6 adult friends for a concert and really enjoyed our stay. The rooftop area you have all to yourself and was a big hit within our group. It is a short 15-20 minute walk from lots of fun things to do like kayak the river, an animal rescue that you can go pet dogs and the Original Mr. Beef restaurant that the show "The Bear" is based off of. We went to Mr.Beef for great sandwiches and even saw the main actor from the show there!! For sleeping arrangements, it wasn't ideal to...
Breathtaking Downtown Penthouse A - Sleeps 11!
Cozy, King bed with heated bathroom!
9.8 out of 10, Exceptional, (8)
"Great"
Cozy, King bed with heated bathroom!
Stay in the Heart of the City! Complimentary Bicycles for exploring!
10.0 out of 10, Exceptional, (2)
"Enjoyed the walkability of this location to all downtown Chicago has to offer. The onsite amenities were also wonderful"
The price is SAR 747
SAR 967 total
includes taxes & fees
30 Jum. II - 1 Raj.
Stay in the Heart of the City! Complimentary Bicycles for exploring!
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
9.8 out of 10, Exceptional, (9)
"The ceilings are tall and space is welcoming. The tile in the shower was really cool and the towels were perfect. It was nice to have an open kitchen available but I did not need it as the food in the neighborhood was so yummy. The bed was awesome and the pillow was incredible. To top it off a client came over and we played pool. Another thing I enjoyed was the shoes at the door policy… clean spaces start with no shoes and this place is clean and stylish. Great location and I am happy to give...
Modern & Stylish West Town Loft with Pool Table (Pets Allowed)
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (4)
"Neighborhood was quiet! Rental was exactly as shown online. Was able to easily find the rental with no problem. Overall great stay."
Cozy Home Sweet Homewood.
Elegant Mayor's Manor in Central Chicago - 9 Beds
9.6 out of 10, Exceptional, (8)
"Place was as described and worked perfect for our stay."
Elegant Mayor's Manor in Central Chicago - 9 Beds
Pet-Friendly Warrenville Townhome w/ Gas Grill!
10.0 out of 10, Exceptional, (1)
"The townhouse was clean, comfortable and beautifully decorated. The kitchen is well stocked for cooking and dining. There were extra touches to make it a pet friendly stay. The only downside is the noise from the traffic but the townhouse is located close to stores, restaurants and access to the tollway."
Pet-Friendly Warrenville Townhome w/ Gas Grill!
NEW Spacious and Comfy Duplex - 55" & 50" Smart TVs, Workspace, Cul-de-sac
9.0 out of 10, Wonderful, (2)
"The neighborhood is great, very nice house with very firm beds. Thank you"
NEW Spacious and Comfy Duplex - 55" & 50" Smart TVs, Workspace, Cul-de-sac
✽ Charming Cottage ✽ close to College/Town/Station
10.0 out of 10, Exceptional, (31)
"Great house thank you"
The price is SAR 638
SAR 1,084 total
includes taxes & fees
15 Raj. - 16 Raj.
✽ Charming Cottage ✽ close to College/Town/Station
Offering Spectacular Stay! Full Kitchen, Pet-friendly, Near Cantigny Golf Club!
8.0 out of 10, Very Good, (3)
"This location was great for us. The room was very nice and quiet. It was great to have a full size fridge and microwave."
The price is SAR 461
SAR 587 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Offering Spectacular Stay! Full Kitchen, Pet-friendly, Near Cantigny Golf Club!
Pink Wild Rose - Ultimate Romantic Getaway
10.0 out of 10, Exceptional, (1)
"The host was great tgey accommodated ys with a 2 hr early check in and the house was amazing"
The price is SAR 964
SAR 1,114 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Pink Wild Rose - Ultimate Romantic Getaway
Stunning 2 Floor Penthouse Downtown
10.0 out of 10, Exceptional, (1)
"Space was great and ability to host a girls weekend was perfect! Thank you."
Stunning 2 Floor Penthouse Downtown
Central Chicago Suite2 Access to Patio!
9.0 out of 10, Wonderful, (4)
"loved the place"
Central Chicago Suite2 Access to Patio!
Immaculate Brand New Condo Downtown!
9.4 out of 10, Exceptional, (3)
"Better than expected"
Immaculate Brand New Condo Downtown!
Don't see what you're looking for?
See all available properties in Orland Park
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.

Other property types in Orland Park

Sentral Michigan Avenue
4.0 star property
9.2 out of 10, Wonderful, (442)
"We stayed overnight after attending a concert at Northerly Island. It was a convenient walk there and back. We also had a beautiful view of Navy Pier. The room was clean, as was the property itself. The staff and residents were friendly. I would stay again and also recommend to anyone thinking about it."
The price is SAR 672
SAR 885 total
includes taxes & fees
17 Jum. II - 18 Jum. II
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.4 out of 10, Very Good, (96)
"The property was very clean and I loved the fact that it had a kitchen for you to cook. What I did not like was that there was no market close enough to buy groceries. I also didn't like the fact that the TV was not accesible for us, even though, I payed the late fees for a late check out. "
The price is SAR 390
SAR 450 total
includes taxes & fees
7 Raj. - 8 Raj.
Sonder Market Hall
Sonder South Wabash
3.5 star property
8.8 out of 10, Excellent, (314)
"Comfortable to stay"
The price is SAR 599
SAR 691 total
includes taxes & fees
2 Raj. - 3 Raj.
Sonder South Wabash
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.

Recent reviews of Orland Park hotels
Expedia verified reviews