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Compare Vacation Homes in Crestwood with updated reviews, rates, and availability.

"We rented this house so that two families could stay for the weekend in Chicago to celebrate our kids engagement. The house is great, it's pet friendly, it's in a great location, the garage is very useful for parking cars, etc. However, you really, really need to read the owner's rules. If you read the listing's first part "great place for your friends and family gathering", "

"Awesome stay!"

AED 1,169 total

includes taxes & fees

14 Jan - 15 Jan

"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!"

"Good stay. "

"Everything was nice and cleaned.Will stay again "

AED 1,161 total

includes taxes & fees

26 Jan - 27 Jan

"We had a short stay in this property and we wished it could have been longer. The house was very nice, clean and the communication was great!! It is a short drive to the airport and to downtown. We would definitely stay here again"

AED 1,371 total

includes taxes & fees

14 Jan - 15 Jan

"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."

"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. "

"I stayed in this home for two nights. It was cold as ever. The heat did not work at all, no matter how high I turned it up and I couldn’t even heat up my food in the microwave because that didn’t work either. My food was not getting warm no matter how long I put it on in the microwave me and my company was cold For both nights."

Matteson Vacation Rental | 4BR | 2.5BA | 1,800 Sq Ft | Stairs Required

"We really love the home and the setup."

BEAUTIFUL 4-story home located in one of Chicago’s safest neighborhoods!

"Our group consisted of 8 people ranging from preteens to octogenarians and we all really enjoyed this townhome! It was attractive, clean, updated and stylish, yet retained some of the historic ambiance of the neighborhood. Beds were comfy. Bedrooms are attractively decorated. Kitchen was roomy and easy to work in. Aga stove was a new experience, but after a short learning curve, we mastered it. The youngest members claimed the top floor as their space, which worked well. The home is a short walk...

AED 1,839 total

includes taxes & fees

24 Jan - 25 Jan

Oak Park Vacation Rental | 3BR | 1BA | 1,500 Sq Ft | 6 Steps Required

"We really enjoyed our stay here. It's a great area - walking distance to several great restaurant options! Our only frustrations were the lack of toilet paper (2 rolls for 5 people staying for 5 days) and lack of supplies for the oven (cookware only available for stovetop). Other than that, I'd highly recommend staying here. "

"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. "