Book Holiday Homes in Crestwood

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Featured Holiday Homes in Crestwood

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

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

Chicago
Located in Chicago (Humboldt Park), this vacation home is within a 10-minute drive of United Center and Michigan Avenue.
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars

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

Chicago
With a stay at this vacation home in Chicago (Near North Side), you'll be within a 5-minute drive of Michigan Avenue and Lake Michigan.
Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars
Spacious 3br home near Chicago, fenced yard for pets

Spacious 3br home near Chicago, fenced yard for pets

2 out of 5
Richton Park
The price is AU$487 per night from 17 Feb to 18 Feb
AU$487
includes taxes & fees
17 Feb - 18 Feb
Located in Richton Park, this vacation home is a 4-minute drive from Hanger Clinic and 6 minutes from Winnebago Dog Park.
Spacious 3br home near Chicago, fenced yard for pets
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Gorgeous historic mansion on UChicago campus. Renovation with original detail.

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

Chicago
With a stay at this vacation home in Chicago (Hyde Park), you'll be within a 5-minute drive of Lake Michigan and University of Chicago.
Gorgeous historic mansion on UChicago campus. Renovation with original detail.
Luxury Home Away From Your Home

Luxury Home Away From Your Home

Chicago
With a stay at this vacation home in Chicago (East Garfield Park), you'll be within a 5-minute drive of United Center and University of Illinois Chicago.
Luxury Home Away From Your Home
Cheerful 4 bedroom smart home w/ indoor fireplace

Cheerful 4 bedroom smart home w/ indoor fireplace

Chicago
With a stay at this vacation home in Chicago (Washington Park), you'll be within a 5-minute drive of State Street and University of Chicago.
Cheerful 4 bedroom smart home w/ indoor fireplace
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!

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

Chicago
With a stay at this vacation home in Chicago (Humboldt Park), you'll be within a 10-minute drive of United Center and Michigan Avenue.
Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover

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

Chicago
With a stay at this vacation home in Chicago (Near North Side), you'll be within a 5-minute drive of Michigan Avenue and Lake Michigan.
Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover
Berwyn Beauty

Berwyn Beauty

Berwyn
With a stay at this vacation home in Berwyn, you'll be within a 15-minute drive of United Center and University of Illinois Chicago.
Berwyn Beauty
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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.

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
364 Holiday Homes
Lowest Price
AU$158
Highest Price
AU$487
Popular accommodation
Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars, Spacious 3br home near Chicago, fenced yard for pets, Gorgeous historic mansion on UChicago campus. Renovation with original detail., Luxury Home Away From Your Home, Cheerful 4 bedroom smart home w/ indoor fireplace, Spacious / New Home - 8BD/4BTH - Sleeps 16 + Garage!, Old Town 3bd 3ba Coach House, Garage Parking Incl by AllSet Turnover, Berwyn Beauty

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$158 per night from 17 Feb to 18 Feb
AU$158
includes taxes & fees
17 Feb - 18 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$222 per night from 17 Feb to 18 Feb
AU$222
includes taxes & fees
17 Feb - 18 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
Hilton Chicago

Hilton Chicago

4 out of 5
720 S Michigan Ave, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$321 per night from 28 Feb to 1 Mar
AU$321
includes taxes & fees
28 Feb - 1 Mar
With a stay at Hilton Chicago, you'll be centrally located in Chicago, within a 10-minute walk of Buckingham Fountain and Art Institute of Chicago.
Hilton Chicago
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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 19 Feb to 20 Feb
AU$188
includes taxes & fees
19 Feb - 20 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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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.