Book Holiday Homes in Crestwood

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Featured Holiday Homes in Crestwood

Cozy Home Sweet Homewood.

Cozy Home Sweet Homewood.

Homewood
With a stay at this vacation home in Homewood, you'll be within a 5-minute drive of Ravisloe Country Club and Oak Hill Park.
Cozy Home Sweet Homewood.
Updated Forest Park 3 BR Bungalow

Updated Forest Park 3 BR Bungalow

Forest Park
With a stay at this vacation home in Forest Park, you'll be within a 15-minute drive of United Center and Art Institute of Chicago.
Updated Forest Park 3 BR Bungalow
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
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Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover

825 S Claremont, Chicago, IL
With a stay at this vacation home in Chicago (Near West Side), you'll be within a 5-minute drive of United Center and University of Illinois Chicago.
Newly Updated Vintage 6 Bedroom Single Family Home 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
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!
LUXE 3 BR, 2 BA + Hot Tub

LUXE 3 BR, 2 BA + Hot Tub

Elmhurst
The price is AU$638 per night from 6 Apr to 7 Apr
AU$638
includes taxes & fees
6 Apr - 7 Apr
With a stay at this vacation home in Elmhurst, you'll be within a 5-minute drive of Elmhurst Hospital - Main Campus and Oak Brook Golf Course.
LUXE 3 BR, 2 BA + Hot Tub
Private Home Awaits

Private Home Awaits

Homewood
With a stay at this vacation home in Homewood, you'll be within a 5-minute drive of Coyote Run Golf Course and Advocate South Suburban Hospital.
Private Home Awaits
Spacious 5-bedroom house with movie room, game room and more!

Spacious 5-bedroom house with movie room, game room and more!

Berwyn
Located in Berwyn, this vacation home is within a 15-minute drive of United Center and Art Institute of Chicago.
Spacious 5-bedroom house with movie room, game room and more!
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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
462 Holiday Homes
Lowest Price
AU$171
Highest Price
AU$638
Popular accommodation
Cozy Home Sweet Homewood. , Updated Forest Park 3 BR Bungalow, Huge 5 BR Home // Private Yard // Walk Everywhere // Parking for 2 Cars, Newly Updated Vintage 6 Bedroom Single Family Home by AllSet Turnover, Berwyn Beauty, Stylish 5BR/3BA - 2 Units - 2 Kitchens + Parking!, LUXE 3 BR, 2 BA + Hot Tub, Private Home Awaits, Spacious 5-bedroom house with movie room, game room and more!

Top trending hotels in Crestwood

Crowne Plaza Chicago West Loop by IHG

Crowne Plaza Chicago West Loop by IHG

3.5 out of 5
25 South Halsted Street, Chicago, IL
Fully refundable
The price is AU$171 per night from 20 Apr to 21 Apr
AU$171
includes taxes & fees
20 Apr - 21 Apr
Located in Chicago (Downtown Chicago), Crowne Plaza Chicago West Loop by IHG is within a 15-minute walk of University of Illinois Chicago and Willis Tower.
Crowne Plaza Chicago West Loop by IHG
Embassy Suites by Hilton Chicago Downtown River North

Embassy Suites by Hilton Chicago Downtown River North

4 out of 5
600 N State St, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$246 per night from 13 Apr to 14 Apr
AU$246
includes taxes & fees
13 Apr - 14 Apr
With a stay at Embassy Suites by Hilton Chicago Downtown River North, you'll be centrally located in Chicago, steps from State Street and 4 minutes by foot from ...
Embassy Suites by Hilton Chicago Downtown River North
Swissotel - Chicago

Swissotel - Chicago

4.5 out of 5
323 E Wacker Dr, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$377 per night from 16 Apr to 17 Apr
AU$377
includes taxes & fees
16 Apr - 17 Apr
A stay at Swissotel - Chicago places you in the heart of Chicago, within a 10-minute walk of Michigan Avenue and Millennium Park.
Swissotel - Chicago
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River Hotel

River Hotel

4 out of 5
75 East Wacker Drive, Chicago, IL
Fully refundableReserve now, pay when you stay
The price is AU$183 per night from 20 Apr to 21 Apr
AU$183
includes taxes & fees
20 Apr - 21 Apr
With a stay at River Hotel, you'll be centrally located in Chicago, steps from Michigan Avenue and 5 minutes by foot from Chicago Riverwalk.
River Hotel
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See all available properties in Crestwood
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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.