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Compare 373 Vacation Homes in Crestwood with updated reviews, rates, and availability.

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

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

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

9.4 out of 10, Exceptional, (86)
"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", "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

Spacious 3br home near Chicago, fenced yard for pets

2.0 star property
10.0 out of 10, Exceptional, (2)
"Awesome stay!"
The price is SAR 450
SAR 1,152 total
includes taxes & fees
2 Feb - 3 Feb
Spacious 3br home near Chicago, fenced yard for pets

Charming 3-bedroom house in Calumet City with WiFi and AC

10.0 out of 10, Exceptional, (3)
"Tammara is a perfect host! She is nice and accommodating. The check in process was very smooth. The house was spotless and so nice! I will definitely be booking again. "
The price is SAR 563
SAR 1,080 total
includes taxes & fees
2 Feb - 3 Feb
Charming 3-bedroom house in Calumet City with WiFi and AC

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

10.0 out of 10, Exceptional, (3)
"I wish we came across this property 4 years ago when we dropped off our daughter at the UofC campus. Location is amazing, 7 minutes walk to the campus. The house is spacious and accommodates a large group of people. Very clean and what was really appreciated it was so well stocked - nice shampoos and lotions in all bathrooms, paper towels in the kitchen, a welcome bottle of bubbly wine from the hosts. The check-in and out process was also incredibly easy, and the hosts were very welcoming and...
Gorgeous historic mansion on UChicago campus. Renovation with original detail.

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

Cheerful 4 bedroom smart home w/ indoor fireplace

7.8 out of 10, Good, (12)
"Loved the place and host was super helpful when needed! "
Cheerful 4 bedroom smart home w/ indoor fireplace

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

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

9.8 out of 10, Exceptional, (6)
"Great location so convenient to everything! Great to have a garage to park. Also, great to have the 2 bedrooms with their own bathrooms! Property met our needs. It was not dirty but was not as clean as it could have been. (Mainly the floors) Overall the house worked great for us! "
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

Staycation Retreat

2.0 star property
6.4 out of 10, (5)
"My stay was good it was spacious was cuteee ! And perfect for my group !"
The price is SAR 446
SAR 912 total
includes taxes & fees
4 Feb - 5 Feb
Staycation Retreat

Berwyn Beauty

10.0 out of 10, Exceptional, (12)
"Perfect for visiting family by with more space than an hotel. A nice neighborhood. Away from the hustle and bustle of downtown but an easy drive for vacationers. "
Berwyn Beauty

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

Stunning 4-bedroom 4-bath building in Wicker Park! + Parking

LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

9.4 out of 10, Exceptional, (3)
"Good stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

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

9.6 out of 10, Exceptional, (46)
"The home was updated and very clean. The kitchen was large and was well stocked. The owner provided everything you would need to cook. The fenced in yard was a bonus as we traveled with our dog. The neighborhood is older and safe. The neighboring homes are well maintained. The street in front of the house is busy during rush hour, but didn't create an issue pulling out into traffic. We did not experience noise from the traffic. We had one small glitch which was taken care of quickly. The...
The price is SAR 596
SAR 1,333 total
includes taxes & fees
24 Feb - 25 Feb
The Comfy King Ranch - King Bed/Spacious Home/Fast WiFi/Free Parking

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

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (44)
"Fantastic house…whole family enjoyed our stay. Thank you!"
Luxury House in the heart of Old Town with Parking

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 1,031
SAR 1,709 total
includes taxes & fees
12 Feb - 13 Feb
LUXE 3 BR, 2 BA + Hot Tub

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!

Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

10.0 out of 10, Exceptional, (33)
"We had a terrific stay at here. The apartment was sparkly clean. The linens were like new. The bed was comfortable and cozy. It’s a basement apartment but you don’t feel “underground” at all. It’s light and airy, laid out well with plenty of living space. It’s on a quiet residential block and conveniently located for public transportation and walking to restaurants. Caitlin checked in with us just the right amount—to be sure the temperature was right (it was) and if we needed anything (we...
Private, Cozy Urban Oasis Chicago Greystone In Heart of Logan Square

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
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, (670)
"Sandra and Joy are welcoming and helpful. Great front desk."
The price is SAR 411
SAR 593 total
includes taxes & fees
2 Feb - 3 Feb
Sentral Michigan Avenue

Sonder Market Hall

3.5 star property
8.6 out of 10, Excellent, (250)
"Enjoyed My Stay."
The price is SAR 424
SAR 498 total
includes taxes & fees
20 Feb - 21 Feb
Sonder Market Hall

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (426)
"Property was convenient and clean. Overall great experience. Street meter parking could be a headache during parking hours but it’s a city thing. Also the incidental feee is a bit confusing with how it’s returned. "
The price is SAR 354
SAR 416 total
includes taxes & fees
25 Feb - 26 Feb
Sonder South Wabash
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.