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Compare 413 Vacation Homes in Orland Park with updated reviews, rates, and availability.

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (19)
"This was perfect for our needs. Great location, comfortable and clean. I'm sure we'll be back."
Cozy Home Sweet Homewood.

Cozy 3-bedroom house in family-oriented Melrose Park.

10.0 out of 10, Exceptional, (4)
"This is a great place and very pet friendly. Only negatives were lack of hashtags (only one in the home), no hair dryer when it advertised it had one, and no TV in any of the bedrooms. The home was clean, spacious, fireplace and hot tub are a great bonus."
Cozy 3-bedroom house in family-oriented Melrose Park.

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
9.2 out of 10, Wonderful, (5)
"As advertised. We enjoyed our stay. Thank you!"
The price is SAR 510
SAR 1,209 total
includes taxes & fees
24 Mar - 25 Mar
Spacious 3br home near Chicago, fenced yard for pets

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (21)
"Hot tub was nice, the house itself was clean and had a great backyard that is big and pretty. Host is very responsive. Recommend!!"
The price is SAR 844
SAR 1,497 total
includes taxes & fees
17 Mar - 18 Mar
LUXE 3 BR, 2 BA + Hot Tub

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (13)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!

Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

10.0 out of 10, Exceptional, (3)
"Upscale tri level home, easy location to get to and Uber from. House is very well designed and set up for a larger family group. 4 nice bedrooms with really nice bathrooms and a small workout area. Living room and kitchen open up to a back deck area with lower level sitting spaces. Great place to stay for concerts or just an easy location to visit the pier or soldier field or Wrigley or white Sox. We enjoyed our week. "
Remodeled 1890 Chicago Greystone, 4bd 3.5ba & Gym

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.4 out of 10, Exceptional, (10)
"House was clean and the check in process was easy. The gated driveway easily fit 3 cars with room to spare."
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (98)
"This Forest Park bungalow was perfect for our ladies weekend. It is clean, comfortable, updated, charming, well stocked with supplies, has off-street parking, and is convenient to the city. I highly recommend this lovely home."
Updated Forest Park 3 BR Bungalow

Private Home Awaits

The price is SAR 675
SAR 1,618 total
includes taxes & fees
12 Mar - 13 Mar
Private Home Awaits

Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

9.0 out of 10, Wonderful, (7)
"To say we enjoyed our stay, is an understatement. My sister was able you bring in her 21st birthday properly along with her close friends. It was so spacious, everyone had their own area to hang out. The master bedroom is gorgeous, a real selling point. My only regret is that it is winter && we were unable to enjoy the backyard. Our host was amazing and very helpful during the whole process, any question was promptly answered. If you’re looking for a nice place in a quiet area, don’t hesitate to...
Renovated 6 Bedroom 5 Bathroom Home 10 Minutes from Downtown Chicago

Gorgeous historic mansion on UChicago campus. Renovation with original detail.

10.0 out of 10, Exceptional, (4)
"Delightful home in charming neighborhood. The host was great to deal with, making sure we had what we needed for our toddler. All we had to bring was ourselves!"
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

9.6 out of 10, Exceptional, (47)
"Nice property with 3 bedrooms & a fenced in back yard. Great communication with owner. "
The price is SAR 596
SAR 1,315 total
includes taxes & fees
31 Mar - 1 Apr
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

10.0 out of 10, Exceptional, (4)
"A few work colleagues and I were in town for a convention at McCormick Place, and sought out a place that would work well for us, and be close to the convention hall. This location was great- each guest had a room and their own private bathroom (each one with a comfortable toilet/bidet!) The kitchen area served its purpose just fine, the living/gathering room was a bit on the small side, but the neighborhood was very quiet. We could walk to numerous restaurants and never felt unsafe. We would...
4 #2N - 4 Bedroom / 4 Bath Condo - McCormick Place, Wintrust Arena, Chinatown

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (73)
"Our party came to town to visit relatives during Christmas holidays. The house was in good working order and met our needs. Beds were comfortable with easy check- in/ check- out."
Furnished Private home in Aurora sleeps 9 guests

Chic 3bed 2bath Home with free parking close to United Center

9.8 out of 10, Exceptional, (10)
"Everything was perfect "
The price is SAR 938
SAR 1,603 total
includes taxes & fees
18 Mar - 19 Mar
Chic 3bed 2bath Home with free parking close to United Center

Lux Home in Chicago 7mins Downtown

9.8 out of 10, Exceptional, (16)
"Beautiful stay and super nice host would recommend every time "
Lux Home in Chicago 7mins Downtown

Berwyn Beauty

10.0 out of 10, Exceptional, (13)
"Amazing... location, price, amenities, etc."
Berwyn Beauty

Cozy 5-bedroom with lake views and spacious deck

10.0 out of 10, Exceptional, (8)
"This was our 2nd year in a row staying here. Everything was great yet again. I highly recommend this house for anyone staying in the area."
Cozy 5-bedroom with lake views and spacious deck

2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

9.2 out of 10, Wonderful, (15)
"Great quiet place. "
2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

Cozy house in the city

2.0 star property
10.0 out of 10, Exceptional, (1)
"Very nice house and host was very thoughtful. Will definitely stay again when coming back to Chicago. "
Cozy house in the city
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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Other property types in Orland Park

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (695)
"Nice "
The price is SAR 475
SAR 668 total
includes taxes & fees
12 Mar - 13 Mar
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (447)
"A great stay! I’d definitely come back."
The price is SAR 353
SAR 414 total
includes taxes & fees
1 Apr - 2 Apr
Sonder South Wabash

Sonder The Burnham Apartments

3.5 star property
8.8 out of 10, Excellent, (146)
"Amazing place to go relax and get peace. Definitely a must "
The price is SAR 471
SAR 553 total
includes taxes & fees
1 Apr - 2 Apr
Sonder The Burnham Apartments
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.