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Compare 468 Vacation Homes in Crestwood with updated reviews, rates, and availability.

Cozy Home Sweet Homewood.

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

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

Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

9.2 out of 10, Wonderful, (89)
"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."
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

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

Berwyn Beauty

10.0 out of 10, Exceptional, (14)
"Communication was amazing. Home was very welcoming, clean, and well prepared. Had a wonderful stay! "
Berwyn Beauty

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!

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 844
SAR 1,497 total
includes taxes & fees
28 Apr - 29 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

Spacious and Sleek 4BD/2.5BA - Logan Square!

9.4 out of 10, Exceptional, (18)
"The unit is spacious but we only found 3 bedrooms not 4 as advertised. However it had 4 queen beds in 3 bedrooms. The bathrooms and carpet were not as clean as I like to see. The towels were small & thin with no extras to be found. The kitchen is nice but had little stock. The owner communicated well before the booking. The neighborhood is just ok. We were rarely at the unit except to sleep and get ready as the 5 of us were in town for a family wedding so lots of family events to attend. "
Spacious and Sleek 4BD/2.5BA - Logan Square!

Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

9.6 out of 10, Exceptional, (8)
"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."
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Luxury Home Away From Your Home

9.0 out of 10, Wonderful, (116)
"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

Chicago West Town Row House

2.0 star property
Chicago West Town Row House

Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC

10.0 out of 10, Exceptional, (1)
"Lovely new (or well remodeled?) house in a nice neighborhood. Host was nice and communicative. Kitchen is well stocked. There’s only one shower but we had no problem sharing. "
Charming 3-bedroom house in serene and lovely Evergreen Park. WiFi/ AC

Chic & Stylish 3-bedroom house in Palos Heights

8.0 out of 10, Very Good, (1)
"We enjoyed our stay at this vrbo property - it was very conveniently located as we were visiting family in the Palos Heights area and there are grocery stores and other shopping and restaurants within a few minutes drive. The property was clean and had most basic conveniences like shampoo, conditioner, dish soap, and detergent. The only surprise was that there was another group staying in the basement (with a separate entrance) which wasn't mentioned at all in the property description. "
Chic & Stylish 3-bedroom house in Palos Heights

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

10.0 out of 10, Exceptional, (5)
"We recently stayed at this beautiful vacation rental house with our extended family. We could not have asked for a better experience!The house was incredibly spacious and well-designed, providing ample room for everyone to relax and enjoy their stay. The bedrooms and bathrooms were spacious, comfortable and sparkling. The common spaces on the ground floor were perfect for gathering our group. We enjoyed our meals in the kitchen and dining area. The kitchen was well equipped with cookware, dinner...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
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 Crestwood

Sentral Michigan Avenue

4.0 star property
9.2 out of 10, Wonderful, (722)
"I like the view of this place, had a good few of the park and could see Michigan lake in the distance. Pretty cool that it had a wash and dryer, was not expecting that when we came. Like that it’s in walking distance from the museums, made traveling easy. Employees were also very helpful. "
The price is SAR 412
SAR 593 total
includes taxes & fees
13 Apr - 14 Apr
Sentral Michigan Avenue

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (463)
"Great!"
The price is SAR 412
SAR 484 total
includes taxes & fees
6 Apr - 7 Apr
Sonder South Wabash

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (269)
"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
21 Apr - 22 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.