Book Holiday Homes in Crestwood
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Featured Holiday Homes in Crestwood

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!
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 |
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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! |
Holiday Homes in Crestwood
Top Locations for Holiday Homes in Crestwood
Top trending hotels in Crestwood

Crowne Plaza Chicago West Loop by IHG

Embassy Suites by Hilton Chicago Downtown River North

Swissotel - Chicago

River Hotel
More ways to explore Crestwood
Top picks
**Terms and Conditions apply.
^Subject to availability and chosen travel dates.