Woolooware Vacations from $1,549

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Your Woolooware Vacation

Our Woolooware vacation packages are a simple and practical way to organize and book your next exciting adventure. Discover the heart and soul of this unique neighborhood without the hassle of having to plan everything yourself. When it's time to get out and explore, you'll find loads of popular attractions nearby including Cronulla Beach, Westfield Miranda Shopping Center and Wanda Beach. Visit one, two or more during your trip to Woolooware. Expedia can help turn your dream Woolooware vacation into reality, whatever your travel plans or budget.

The Latest Woolooware Vacation Packages

Price found within the past 48 hours. Click for updated prices.
North-east Facing Modern 2-bed Apartment

North-east Facing Modern 2-bed Apartment

Freshwater
$1,549
per person
Nov 16 - Nov 21
found 18 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
No reviews
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
$1,795
per person
Nov 13 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
8.2/10 Very Good! (2,903 reviews)
YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

Sydney Central Business District
$1,885
per person
Nov 13 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
8.6/10 Excellent! (1,004 reviews)
The York by Swiss-Belhotel International

The York by Swiss-Belhotel International

Sydney Central Business District
$2,099
per person
Nov 13 - Nov 19
found 1 day ago
Roundtrip non-stop flight included
New York (JFK) to Sydney (SYD)
8.6/10 Excellent! (2,745 reviews)
Establishment Hotel

Establishment Hotel

Sydney Central Business District
$1,680
per person
Dec 12 - Dec 13
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
9/10 Wonderful! (696 reviews)
We were welcomed by Emily at Front of House who was so helpful. She gave us great recommendations and really made us welcome. My only disappointment was due to booking through Expedia only 1 breakfast was included whereas if we had booked direct both guests would receive breakfast. Otherwise the stay was ideal. The area is great, 10 minute walk to most places, circular quay, the rocks, old sydney, the shopping area in Pitt Street.

Reviewed on Sep 7, 2026

Where to stay in Woolooware

Find the best Woolooware areas and neighborhoods for the activities you enjoy most. Learn more about Woolooware
A historic clock tower with a modern skyscraper in the background.

Sydney Central Business District

3 out of top 10 points of interest in this area

Historical and commercial heart of Sydney, the CBD boasts towering skyscrapers, lively café culture, and nightlife in areas like Darling Harbour. Explore parks such as Hyde Park and cultural institutions, while enjoying easy access to public transport.

Find hotels in Sydney Central Business District
A nighttime cityscape with illuminated buildings reflecting on the water.

Darling Harbour

Adjacent to Sydney's city centre, Darling Harbour boasts a pedestrian precinct with attractions like the Australian National Maritime Museum and Chinese Garden of Friendship. Enjoy dining at Cockle Bay Wharf, explore Tumbalong Park, and access various transport options, including the Inner West Light Rail and ferry services.

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A large, arched building with multiple entry points, including signs for 'Entry' and 'No entry'.

Sydney Olympic Park

2 out of top 10 points of interest in this area

Featuring a large sports and entertainment area, commercial developments, and extensive parklands, this Greater Western Sydney suburb offers attractions like Bicentennial Park and Newington Armory. Easily accessible via Olympic Park railway line and ferry services.

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A crowded beach with people sunbathing and swimming, surrounded by buildings and trees.

Manly

Beach-side suburb with easy ferry access, Manly offers a mix of ocean and harbor beaches, scenic cycle tracks, and a lively commercial area along The Corso. Explore historic sites like North Head Quarantine Station and enjoy outdoor dining.

Find hotels in Manly
A beach with waves, a woman running, and buildings in the background.

Bondi Beach

1 out of top 10 points of interest in this area

See a perfect example of the Australian beach lifestyle in this famous Sydney neighborhood with ocean pools, excellent surf and a bustling brunch scene.

Find hotels in Bondi Beach

Woolooware Hotel Deals

Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
$240 nightly
$263 total
Oct 11 - Oct 12
Total with taxes and fees
Four Seasons Hotel Sydney
Shangri-La Sydney

Shangri-La Sydney

176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
$213 nightly
$234 total
Oct 11 - Oct 12
Total with taxes and fees
9.2/10 Wonderful! (2,853 reviews)
"Room was dirty with blood stain on pillow, mould in the shower and hair in the shower. Staff were attentive when reported however should never happened. We had breakfast there as well. Not that great… Hotel rooms are dated and needs a total revite. Don’t stay at the Shangri La in Sydney. There are ..."

Reviewed on Sep 20, 2026

Shangri-La Sydney
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

252 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
$103 nightly
$114 total
Oct 11 - Oct 12
Total with taxes and fees
YEHS Hotel Sydney Harbour Suites
See all 5,713 properties in Woolooware
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.
All Inclusive Vacations
All Inclusive Vacations
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Where to go when
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Honeymoon Vacations
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Yoga Vacations
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Solo Vacations

Stay near popular Woolooware attractions

Endeavour Field

9.0/10 (2 reviews)
Catch an event at Endeavour Field during your trip to Sydney. Check out the shops and top-notch restaurants in this walkable area.
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Woolooware Golf Course

Enjoy a round of golf in Sydney at Woolooware Golf Course. Stroll along the beaches or visit the shops while you're in the area.
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Bay Central Woolooware

You can find the perfect gifts to bring home at Bay Central Woolooware during your trip to Sydney. Stroll along the beaches or visit the shops while you're in the area.
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Shark Stadium

Catch an event at Shark Stadium during your trip to Sydney. Stroll along the beaches or visit the shops while you're in the area.
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Things to do

Sydney Grand Tour by Helicopter

Sydney Grand Tour by Helicopter

$268
per adult
Sydney Grand Tour by Helicopter
Sydney: Maroubra Surf Lesson

Sydney: Maroubra Surf Lesson

$61
per adult
Sydney: Maroubra Surf Lesson
Sydney's Secret Bars Nightlife Tour

Sydney's Secret Bars Nightlife Tour

$52
per adult
100% of travellers recommend
Sydney's Secret Bars Nightlife Tour
See all activities in Sydney
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.