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Compare 393 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!

Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

10.0 out of 10, Exceptional, (6)
"Stayed here with six others for a girls trip.The house was beautifully decorated, beds were comfy, and the backyard was such a nice spot to hang out in during our downtime. We loved how much space we had and the attention to the vibes. Adam was super helpful and responsive before and during our stay. We all wished our trip was longer!"
Bee's Knees - Ritzy, 1924 Hollywoodesque Bungalow

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!

Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

9.6 out of 10, Exceptional, (80)
"easy communication, great place, great location. no notes! "
Elegant 4 br Old Town Home; Private Yard; Parking; Amazing Location

Woodlawn Oasis...10 Minutes to Dining & Downtown

9.6 out of 10, Exceptional, (10)
"The property has lots of space and a game room, ideal for a fun getaway with a large group. Close to bus stops and Metra station (different from metro station, we learned this the hard way). Walking distance from the U of Chicago."
Woodlawn Oasis...10 Minutes to Dining & Downtown

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

10.0 out of 10, Exceptional, (2)
"The property was very nice and spacious. The location was great and the parking in the back was amazing. We felt safe and happy our whole stay. "
LuxHome up to 8 guests in Chicago; WiFi, AC, Heat, Security cams, Downtown 8mins

LakeHouse

10.0 out of 10, Exceptional, (13)
"Overall great experience! Great home, I love the decor of the entire home. And I will definitely recommend to others and will book again "
LakeHouse

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

Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

10.0 out of 10, Exceptional, (88)
"We had a fantastic trip, house great for us Cary was very helpful "
Beautiful Modern Designer Home ~ Downtown - 4-Bed/4-Bath

Full Luxurious Modern House Near Chicago

3.4 out of 10, (6)
"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."
Full Luxurious Modern House Near Chicago

Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

8.2 out of 10, Very Good, (20)
"We really love the home and the setup."
Home w/ Yard & Patio ~ 30 Mi to Downtown Chicago

PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

9.8 out of 10, Exceptional, (12)
"We really enjoyed this beautiful home and location for our family trip. The large rooms and open floor plan were perfect for six adults to enjoy. Plenty of local restaurants and shopping nearby. This was also a nice safe neighborhood for evening strolls and we enjoyed the Christmas lights on display."
The price is SAR 792
SAR 1,692 total
includes taxes & fees
29 Dec - 30 Dec
PROMO 10% WEEKLY AND 15% MONTHLY! Jacuzzi, King Beds, Easy Access to DT Chicago!

UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

9.6 out of 10, Exceptional, (5)
"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...
UP-SCALE Wicker Park 4BD/3.5BA HOME (+garage)

The Grand Kimball Lodge, Logan Square, Sleeps 14

10.0 out of 10, Exceptional, (1)
The Grand Kimball Lodge, Logan Square, Sleeps 14

858 Orleans

3.0 star property
858 Orleans

Cozy 3-bedrooms w/ full kitchen bungalow in Chicago area (15-mins to downtown)

2.0 star property
5.4 out of 10, (3)
"We called and asked was small gatherings allowed and they said yes and they still managed to call police and kick us out "
The price is SAR 770
SAR 1,346 total
includes taxes & fees
27 Dec - 28 Dec
Cozy 3-bedrooms w/ full kitchen bungalow in Chicago area (15-mins to downtown)

Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

2.0 star property
10.0 out of 10, Exceptional, (2)
"Very clean in a safe neighborhood. I would stay here again"
The price is SAR 597
SAR 820 total
includes taxes & fees
30 Dec - 31 Dec
Charming 3-BR home on a cobblestone street near the Lake Michigan lakefront.

8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

5.4 out of 10, (3)
"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. "
8 Mi to Chicago: Oak Park Home w/ Fenced Backyard!

Charming 3-bedroom house in awesome Chicago with AC, WiFi

Charming 3-bedroom house in awesome Chicago with AC, WiFi

LUXE 3 BR, 2 BA + Hot Tub

9.0 out of 10, Wonderful, (18)
"."
The price is SAR 676
SAR 1,316 total
includes taxes & fees
8 Jan - 9 January 2025
LUXE 3 BR, 2 BA + Hot Tub
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, (629)
"I have stayed at this property 3 times now and every time has been amazing. They have become the only place I will stay at in the city. The location is great with a parking garage around the corner at is very cheap. You get so many more amenities than a hotel and is an overall great experience. I highly recommend."
The price is SAR 412
SAR 593 total
includes taxes & fees
29 Dec - 30 Dec
Sentral Michigan Avenue

Kasa Magnificent Mile Chicago

4.0 star property
9.2 out of 10, Wonderful, (343)
"Great stay "
Kasa Magnificent Mile Chicago

Sonder South Wabash

3.5 star property
9.0 out of 10, Wonderful, (407)
"Outstanding accommodations! Will choose this property again for my travels."
The price is SAR 466
SAR 547 total
includes taxes & fees
15 Jan - 16 January 2025
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.