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Compare 469 Vacation Homes in Orland Park with updated reviews, rates, and availability.

Cozy Home Sweet Homewood.

9.8 out of 10, Exceptional, (22)
"Liked very much"
Cozy Home Sweet Homewood.

Furnished Private home in Aurora sleeps 9 guests

9.4 out of 10, Exceptional, (75)
"We met our Wisconsin grandbaby and his mom for an extended weekend visit. The house was very accommodating and spacious. The neighborhood is conveniently located to everything we wanted to do. We will be back! "
Furnished Private home in Aurora sleeps 9 guests

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

10.0 out of 10, Exceptional, (7)
"Clean and in a nice neighborhood "
Cozy 3-bedroom house in family-oriented Melrose Park.

Updated Forest Park 3 BR Bungalow

10.0 out of 10, Exceptional, (101)
"My friends and I had a wonderful stay at this property. It is very cute and conveniently located in a nice neighborhood (Oak Park/Forest Park areas) with easy access to 290 that takes you straight to the heart of downtown Chicago. The house had many amenities and you can tell the hosts are very considerate/thoughtful. Would highly recommend! "
Updated Forest Park 3 BR Bungalow

Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East

10.0 out of 10, Exceptional, (2)
"This is a very beautiful and amazing place. Great for family stay or group . Clean house , everything listed online is exactly as it is. Food and malls nearby. Overall great accommodation. Will definitely visit again anytime I’m in Chicago. Thank you !"
Spacious 3-Bedroom Home with Game Lounge & Relaxing Backyard Near Glenbard East

Charming ModernRetro Home!

9.2 out of 10, Wonderful, (14)
"Brittany was absolutely amazing. Her home was gorgeous and cozy. Served our needs exact. We will be coming back! "
Charming ModernRetro Home!

Historic home with easy access to Chicago

9.8 out of 10, Exceptional, (163)
"everything about this house was wonderful. The beds were comfortable. Everything was clean. The family had a lot of fun. We were able to invite other family members over to visit. My daughter loved playing the piano, just made the mini family reunion perfect. Thank you for sharing your amazing home."
Historic home with easy access to Chicago

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

9.6 out of 10, Exceptional, (11)
"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

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

9.2 out of 10, Wonderful, (16)
"We had a great stay."
2 King Bdrms and 1 Queen Bdrm! 20 minutes to O'Hare Airport! Parks and Shopping!

Berwyn Beauty

10.0 out of 10, Exceptional, (15)
"We had an amazing time at the Berwyn Beauty. Good location and response time to messages! We Came down for Americas Beauty show and had the most amazing time. "
Berwyn Beauty

LUXE 3 BR, 2 BA + Hot Tub

9.2 out of 10, Wonderful, (23)
"This property was is in a good neighborhood nice and clean I really enjoy myself Thanks"
The price is SAR 845
SAR 1,498 total
includes taxes & fees
13 Apr - 14 Apr
LUXE 3 BR, 2 BA + Hot Tub

Private Home Awaits

10.0 out of 10, Exceptional, (2)
"Very convenient to all my activities for my 55th Birthday "
Private Home Awaits

Spacious 5-bedroom house with movie room, game room and more!

10.0 out of 10, Exceptional, (2)
"This was a great rental experience from start to finish. Everyone was impressed with the space, and the location couldn't be better. We will definitely be back. "
Spacious 5-bedroom house with movie room, game room and more!

House with garage, outdoor dining and basement bar

House with garage, outdoor dining and basement bar

King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House

10.0 out of 10, Exceptional, (29)
"Was good, was not able to change temperature in the house so it was hot "
The price is SAR 863
SAR 1,519 total
includes taxes & fees
11 May - 12 May
King Bed/Fast Wi-Fi/Spacious/Family-Friendly/Just 2 steps to enter House

Great place to stay in Warrenville

10.0 out of 10, Exceptional, (54)
"For some reason the pictures don’t do justice on the house. It’s beautiful, clean, comfortable. I have family in Chicago, and plan on visiting frequently, so I will definitely be back. Thanks again for the accommodations. "
Great place to stay in Warrenville

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (117)
"Had a great time at Ms. Linnie’s place! She was incredibly responsive and helpful. The house was clean and comfortable, and I loved that there were 2 full bathrooms! I was a little nervous about the neighborhood as we were definitely looked at as outsiders, but no one bothered us and we walked to Maxwell Street Polish and back just fine (which is fantastic, btw). I did love the gated yard in back with two parking spots, so we had our own space. Would definitely stay again!"
Luxury Home Away From Your Home

Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

7.8 out of 10, Good, (7)
"I would stay again and the communication was on point. Thank you for having us."
Comfy 4 bedroom Apartment in the center of CHICAGO! 15 mins from Downtown!

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

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
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, (726)
"Great family place to stay. "
The price is SAR 412
SAR 593 total
includes taxes & fees
20 Apr - 21 Apr
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (465)
"Great location to restaurants, grocery and easy to get to convention center or downtown"
The price is SAR 412
SAR 484 total
includes taxes & fees
16 Apr - 17 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (271)
"Very clean l, quiet and well thought out. Had everything we needed and the bed was super comfortable! Great having a 12 cup coffee pot! Parking was close and although not a lot of close options to restaurants or shopping, there were many more options within a 15-20 min walk. Would definitely stay here again!"
The price is SAR 471
SAR 553 total
includes taxes & fees
20 Apr - 21 Apr
Sonder Market Hall
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.