Book Holiday Homes in Crestwood

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Crestwood Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Crestwood vacation homes are the perfect way for you to wing it.

Holiday houses in Crestwood let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Crestwood in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Crestwood adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Crestwood with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Crestwood vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Crestwood Holiday Homes essential information

Accommodation
Holiday Homes
Lowest Price
AU$161
Highest Price
AU$376
Popular accommodation
Congress Plaza Hotel, L7 Chicago by LOTTE, citizenM Chicago Downtown, Pendry Chicago

Top trending hotels in Crestwood

Congress Plaza Hotel

Congress Plaza Hotel

3.5 out of 5
520 South Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$161 per night from 16 Feb to 17 Feb
AU$161
includes taxes & fees
16 Feb - 17 Feb
With a stay at Congress Plaza Hotel, you'll be centrally located in Chicago, steps from Columbia College Chicago and Museum of Contemporary Photography.
Congress Plaza Hotel
L7 Chicago by LOTTE

L7 Chicago by LOTTE

4.5 out of 5
225 N Wabash Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$299 per night from 6 Feb to 7 Feb
AU$299
includes taxes & fees
6 Feb - 7 Feb
With a stay at L7 Chicago by LOTTE, you'll be centrally located in Chicago, steps from Chicago Riverwalk and Chicago Theatre.
L7 Chicago by LOTTE
citizenM Chicago Downtown

citizenM Chicago Downtown

4 out of 5
80 East Wacker Place, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$188 per night from 13 Feb to 14 Feb
AU$188
includes taxes & fees
13 Feb - 14 Feb
A stay at citizenM Chicago Downtown places you in the heart of Chicago, steps from Michigan Avenue and Chicago Riverwalk.
citizenM Chicago Downtown
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Pendry Chicago

Pendry Chicago

4.5 out of 5
230 North Michigan Avenue, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$376 per night from 23 Feb to 24 Feb
AU$376
includes taxes & fees
23 Feb - 24 Feb
With a stay at Pendry Chicago, you'll be centrally located in Chicago, steps from Michigan Avenue and 3 minutes by foot from Chicago Riverwalk.
Pendry Chicago
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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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^Subject to availability and chosen travel dates.