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Featured Holiday Houses in Chippendale

Serviced Waterfront Whole Villa
Serviced Waterfront Whole Villa
3.5 out of 5.0 24 Roper Cres, Sylvania Waters, NSW
AU$225
When you stay at this vacation home in Sylvania Waters, you'll be by the sea, within a 10-minute drive of Cronulla Beach and Wanda Beach.
Darling Harbour Modern 2 Bedroom Terrace
Darling Harbour Modern 2 Bedroom Terrace
3.5 out of 5.0 17 Kirk St, Ultimo, NSW
AU$279
With a stay at this vacation home in Ultimo, you'll be a 3-minute walk from Powerhouse Museum and 9 minutes by foot from International Convention Centre ...
Sydney Executive Garden Apartments
Sydney Executive Garden Apartments
3.5 out of 5.0 7 preston avenue, Engadine, NSW
AU$185
With a stay at Sydney Executive Garden Apartments in Engadine, you'll be within a 15-minute drive of Cronulla Beach and Symbio Wildlife Park.
Glenfield Villas - Sydney
Glenfield Villas - Sydney
4.0 out of 5.0 Hebe Terrace, Glenfield, NSW
AU$340
With a stay at this vacation home in Glenfield, you'll be within a 10-minute drive of Liverpool Hospital and University of Wollongong, South Western Sydney ...
Manly Charming Apartment
Manly Charming Apartment
3.5 out of 5.0 7-9 Gilbert Street, Manly, NSW
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With a stay at this vacation home in Manly, you'll be within a 5-minute drive of Manly Beach and Shelly Beach.
Stunning Inner City House Close to Fish Market
Stunning Inner City House Close to Fish Market
3.5 out of 5.0 Bayview Crescent, Annandale, NSW
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With a stay at this vacation home in Annandale, you'll be within a 5-minute drive of University of Sydney and International Convention Centre Sydney.
City Leafy Terrace
City Leafy Terrace
4.0 out of 5.0 34 Kent Street, Millers Point, NSW
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A stay at this vacation home places you in the heart of Millers Point, within a 15-minute walk of Overseas Passenger Terminal and Circular Quay.
Pearson Villas - Sydney
Pearson Villas - Sydney
3.5 out of 5.0 25 Pearson Street, South Wentworthville, NSW
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With a stay at this vacation home in South Wentworthville, you'll be within a 10-minute drive of Qudos Bank Arena and Parramatta Park.
Manly Beachside 2 Bedroom House
Manly Beachside 2 Bedroom House
4.0 out of 5.0 44 Malvern Avenue, Manly, NSW
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With a stay at this vacation home in Manly, you'll be a 1-minute drive from Manly Beach and 5 minutes from Shelly Beach.
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Chippendale 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 Chippendale vacation homes are the perfect way for you to wing it.

Holiday houses in Chippendale 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 Chippendale 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 Chippendale adventures, obvs.

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


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*Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.