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Compare 489 Vacation Homes in Crestwood with updated reviews, rates, and availability.

"The home is warm and inviting just like the pictures. Parking in the back of the house was easy. We cooked several times, pans, spices and dishes are available. The neighborhood is only about 20 minutes from downtown Chicago. The fenced in yard was perfect for our dog. We enjoyed our stay "

"Hot tub was nice, the house itself was clean and had a great backyard that is big and pretty. Host is very responsive. Recommend!!"

AED 1,354 total

includes taxes & fees

26 Mar - 27 Mar

"We traveled to Chicago for a 3 day visit - this house was in a quiet neighborhood and walking distance to several coffee shops and diners. The house fit our family well and was warm and cozy."

"Perfect for what we needed "

"The house is located in a neighborhood that is easily walkable and has anything you need within walking distance. Metro is located within a few blocks of the house and makes getting around easy."

AED 1,584 total

includes taxes & fees

24 Mar - 25 Mar

"House was clean and the check in process was easy. The gated driveway easily fit 3 cars with room to spare."

"As advertised. We enjoyed our stay. Thank you!"

AED 1,191 total

includes taxes & fees

24 Mar - 25 Mar

Microwave, toaster, cookware/dishes/utensils

"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!"

"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...

"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. "

Full-size fridge, microwave, oven, stovetop

"The location near Old Town was perfect walking distance from Second City and many bars and restaurants. We chose this unit not only for the location but also because the arrangement of the rooms with double queen beds was very convenient for my guests with kids. The kitchen was well stocked and though the living room was a little smaller, there was plenty of room for everyone to spread out. The beds were comfortable. The one thing to note is that the extra family room space on the third floor...

"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!"