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Browse Select Crestwood Vacation Homes

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Amazing 3-bedroom house with WiFi and AC in awesome Chicago

Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

7.8 out of 10, Good, (6)
"The house was immaculate and very spacious. Beautifully decorated. The neighborhood was easy to get in and out of and close enough to downtown. Would highly recommend."
The price is CA $205
CA $331 total
includes taxes & fees
Aug 25 - Aug 26
Charming 2-bedroom house in Maywood with WiFi, AC full basement with sofa bed

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

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

Chic and Spacious Bi-level 3BD in Bucktown!

2.0 star property
9.8 out of 10, Exceptional, (8)
"Property was comfortable, clean, and in a great location."
Chic and Spacious Bi-level 3BD in Bucktown!

A Home Away From Home!

9.6 out of 10, Exceptional, (7)
"Great place to stay. Host responded quickly to questions. Location was good and neighbor was quite. "
A Home Away From Home!

Clarendon Hills Top Floor

6.8 out of 10, (10)
"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

3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

8.0 out of 10, Very good, (2)
"Awesome place in a very good location (quiet neighborhood). The owner was very responsive with communication and the property was very clean & spacious! 10/10!"
3-bedroom building in lovely Westchester with AC, WiFi. Enjoy your stay

Walk to the Beach! Theater-Coffee Bar-Games-Gym

2.0 star property
9.8 out of 10, Exceptional, (14)
"This duplex in Old Town was very tastefully refurbished and decorated. The kitchen is outfitted with the best appliances, including an electric kettle. (Note to hosts: ALWAYS provide a tea kettle of some kind and you'll get an automatic five-star rating from me!) The house is quite roomy and comfortable and the four of us settled in nicely. It's a bit of a walk to the train, but the neighborhood is nice, so you don't mind. I highly recommend."
Walk to the Beach! Theater-Coffee Bar-Games-Gym

Luxury House in the heart of Old Town with Parking

10.0 out of 10, Exceptional, (50)
"We stayed for a number of weeks at the property - it was an excellent stay! The property is exactly as advertised and the owner was extremely helpful, communicative, and responsive throughout. The house is modern, in good condition, and is an excellent location."
Luxury House in the heart of Old Town with Parking

Enjoy Chicago/suburbs 2BR townhouse fully equipped

10.0 out of 10, Exceptional, (7)
"I would recommend to anyone. "
Enjoy Chicago/suburbs 2BR townhouse fully equipped

Cozy Full Home + Free Parking + Fast Wi-fi & Central Area

Cozy Full Home + Free Parking + Fast Wi-fi & Central Area

The Family Retreat, The Family Retreat Oasis

2.0 out of 10, (1)
The Family Retreat, The Family Retreat Oasis

Sleep10 + Brew Bar + Game RM + Walk2Train to CHI + Pets + 1 MI to Brookfield Zoo

Sleep10 + Brew Bar + Game RM + Walk2Train to CHI + Pets + 1 MI to Brookfield Zoo

Chicago Buddha's Abode

Chicago Buddha's Abode

Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!

10.0 out of 10, Exceptional, (4)
"We had a fantastic stay! The property was perfect for kids — safe, clean, and had plenty of space to play. The outdoor space is perfect for morning coffee, lounging, afternoon cocktails, and dinner under the stars. This location was unbeatable, close to everything we wanted to do. Couldn’t have asked for a better spot for a family getaway in the city. Highly recommend!"
Spacious Newly Renovated Home in Lincoln Park w/ Outdoor Living & Dining Area!

Zoo Holiday Retreat beautiful home with parking, near train into Chicago.

10.0 out of 10, Exceptional, (2)
"Excellent location, right by the zoo, the place is well stocked and clean, in a nice neighborhood. Close to attractions and easy to go to other western suburbs of Chicago. Has everything we needed :). The host was great with communicating and was able to allow us to borrow a pack n play as well. Would stay again! "
The price is CA $498
CA $895 total
includes taxes & fees
Aug 25 - Aug 26
Zoo Holiday Retreat beautiful home with parking, near train into Chicago.

Spacious 5-bedroom house great for large groups

10.0 out of 10, Exceptional, (1)
Spacious 5-bedroom house great for large groups

Serene 3 Bedroom Home near Downtown Homewood

Serene 3 Bedroom Home near Downtown Homewood

2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

The price is CA $75
CA $497 total
includes taxes & fees
Aug 25 - Aug 26
2BR, Sleeps7 • Coffee Station, Backyard w/ Grill

Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown

2.0 star property
8.8 out of 10, Excellent, (8)
"We got all the help and instructions needed to easily find this clean, well-supplied apartment with lovely outdoor space attached. And with the Pink Line just a few minutes walk and The Loop just 6 stops away, it was the perfect home base for getting to all that Chicago has to offer!"
Cozy Tiny House - 1BR1BT - 15 Mins from Chicago Downtown
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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