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Compare 378 Vacation Homes in Crestwood with updated reviews, rates, and availability.

Cozy Midway Home
2.0 star property
10.0 out of 10, Exceptional, (12)
"This was a perfect little house to stay for our weekend trip! "
Cozy Midway Home
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
9.8 out of 10, Exceptional, (13)
"Before and throughout the trip the hosts were very responsive and helpful. We fully booked the house and there was plenty of room for us in the common areas and backyard. The neighborhood around also has an excellent coffee shop, bar, and food areas within walking distance. Next time I bring a group to the Bridgeport area I’ll definitely try to book this property again "
Elegant Mayor's Manor in Central Chicago - 9 Beds + Futons, Close to Downtown!
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
10.0 out of 10, Exceptional, (2)
"As good as advertised. Plenty of room for our group. Definitely recommend. "
Amazing 4BR/4BA Oasis w/ Rooftop & Stunning Design
Wicker Park Entire House, Private Yard and Parking!
10.0 out of 10, Exceptional, (7)
"Walking distance to the best pastries you will ever eat (Mindys) and the best Ramen you will ever eat (Oii Star). Walking distance to the best line (Blue Line). Place was great, location was great! "
Wicker Park Entire House, Private Yard and Parking!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
9.4 out of 10, Exceptional, (81)
"Overall a great place to stay. Location is really great. You can walk to all of Old Town. Well equipped property. As the only member of our group that drove, was nice to have a garage! "
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
9.6 out of 10, Exceptional, (79)
"This Old Town property was an excellent base for walking exploration of Lincoln Park (Saturday Farmer's Market was fantastic!) and Old Town itself (lively, with very good food, residential neighborhoods, shops, and entertainment), and had easy access to CTA trains to the Loop, Riverwalk, Millennium Park, and much more, had we had time. 7 adults (seniors) spent four nights, and found the four bedrooms, four bathrooms, large fully-equipped kitchen, and living/dining room/patio provided plenty of...
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location
Spacious 5 BR / King Size Beds + Private Parking!
9.6 out of 10, Exceptional, (8)
"My coworkers and I came to Chicago for a conference and this was the perfect place to stay for it. The rooms were well separated so noise didn't travel between them, and the house was clean and comfortable. The host was extremely accommodating, and it was only a short distance from downtown Chicago."
Spacious 5 BR / King Size Beds + Private Parking!
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
9.2 out of 10, Wonderful, (7)
"The house was good, plenty of space. The steps were hard to get up and down but the upstairs was a nice space. House had a bit of a musty odor and the windows could use a cleaning. One night while watching a movie, we received a text stating we were had a loud party and to keep it down. They must have big brother watching us as the only party going on that night was in the movie. Overall the house was close to the city but in a nice Neiborhood. Having a fenced yard with off street parking...
Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover
Cozy Home Sweet Homewood.
10.0 out of 10, Exceptional, (14)
"My mom and I live in Huntsville Alabama and came to visit family and friends in the area and the Homewood house was the perfect location to stay. I miss home so much. It was very comfortable and cute. I will definitely make reservations for next year. Forget staying in a hotel. 😉😅"
Cozy Home Sweet Homewood.
5 minutes from Midway Int'l Airport Single Family Home.
9.2 out of 10, Wonderful, (5)
"Good area super easy process "
5 minutes from Midway Int'l Airport Single Family Home.
4 Mi to Dtwn Chicago: Modern Home w/ Outdoor Space
2.0 star property
4.0 out of 10, (1)
"This place looks nice in photos but is not ready for renting. It does not have a stocked kitchen or other basic amenities. Owner had to send glasses, silverware, hangers, iron, ironing board via Target on the second day of our stay. The dishwasher doesn’t work. Many of the drawers are broken. The deadbolt front door doesn’t lock from outside. "
4 Mi to Dtwn Chicago: Modern Home w/ Outdoor Space
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
2.0 star property
9.8 out of 10, Exceptional, (6)
"Perfect location outside of Chicago. We were visiting friends in nearby Hinsdale. Place is better than the photos. Easy check in process, great communication with host. Place is perfect, spotless and clean, seems brand new. Comfy beds. Keurig coffee was great. Would stay again. Highly recommend! ! "
Willowbrook Gem 3-bedroom house with AC, WiFi, next to Forest Preserve
Clarendon Hills Top Floor
6.6 out of 10, (4)
"The house was nice, in a quiet area. The bedrooms were great. It was a little nerve wracking when the lower unit was rented, as we didn't want to disturb them. "
Clarendon Hills Top Floor
Beautiful, Remodeled Penthouse Unit in Old Town!
9.2 out of 10, Wonderful, (17)
"So much fun! Dan was very communicative "
Beautiful, Remodeled Penthouse Unit in Old Town!
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
9.2 out of 10, Wonderful, (43)
"The building is in a great spot! There are challenges though. The biggest things: 4th floor walk up - no elevator. Old building so tromping up and down the stairs is loud and we worried about disturbing the neighbors. For such a large place, seating is sparse. Master bedroom has no usable closet and the en suite shower is missing a glass door so it’s impossible to keep water from getting on the floor. "
HUGE 1700 sqft 3bd West Loop Penthouse w/ Balcony
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
10.0 out of 10, Exceptional, (87)
"The house was simply beautiful, and the hosts were very communicative and on top of things. Would stay here again"
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath
Classic Oak Park Home, 11 Mi to Downtown Chicago!
8.6 out of 10, Excellent, (14)
"Beautiful home Lovely neighborhood Fabulous location Clean Well appointed No Guest Contact Driveway is too narrow for a standard SUV or larger vehicle Needed some attention to detail: Broken chair in dining room Slow drains in upstairs bath "
Classic Oak Park Home, 11 Mi to Downtown Chicago!
Luxe Spacious SFH in Bucktown w/Secure Parking
9.8 out of 10, Exceptional, (10)
"This beautiful home is exactly as advertised. Clean, bright, and room for all of our grown children and their spouses. There are so many amazing restaurants and shops within easy walking distance. We will definitely be back!!! Thanks so very much to our host. "
Luxe Spacious SFH in Bucktown w/Secure Parking
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
9.8 out of 10, Exceptional, (10)
"We rent Vrbo often. They had the most comfy beds out of all of the places we have stayed. They also allow dogs and have a gated yard. This was perfect for our stay in Chicago."
The price is SAR 726
SAR 1,621 total
includes taxes & fees
19 Nov - 20 Nov
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!
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, (587)
"It was beautiful,clean and quiet "
The price is SAR 485
SAR 679 total
includes taxes & fees
8 Dec - 9 Dec
Sentral Michigan Avenue
Sonder Market Hall
3.5 star property
8.6 out of 10, Excellent, (203)
"Overall, we really enjoyed our stay! The area was lovely and quiet, so nice to sit at the park right beside! I was worried about the noise when it came to sleeping, but I was able to sleep soundly (i did have noise cancelling headphones on though). The bed was super comyfy! The walls are thin though, we could hear conversations and music. This place was very accommodating! They have everything as stated in their listing. The kitchenette is so great! Staff was very friendly whenever I had...
The price is SAR 258
SAR 303 total
includes taxes & fees
10 Dec - 11 Dec
Sonder Market Hall
Sonder South Wabash
3.5 star property
9.0 out of 10, Wonderful, (390)
"Clean and well located. We had access to the green and red line trains a few stops away from the loop. Entering the building was easy and convenient. Apartment was clean and spacious!! "
The price is SAR 480
SAR 563 total
includes taxes & fees
11 Dec - 12 Dec
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.