Woolooware Vacations from $1,386

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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.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

Sydney Central Business District
$1,386
per person
Nov 10 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
8.4/10 Very Good! (1,005 reviews)
Fabulous location. Close to trains and food. Easy walk to darling harbour. Very comfortable bed. Free bottled water in room. Nice bathroom. Staff very pleasant and helpful

Reviewed on Oct 3, 2026

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
$1,650
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.2/10 Very Good! (2,960 reviews)
it was a great location, loved it. Will definitely book again.

Reviewed on Oct 1, 2026

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

Sydney Central Business District
$1,659
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.6/10 Excellent! (1,002 reviews)
La habitación es pequeña pero el hotel está fabuloso, muy limpio todo, la ropa de cama y toallas nuevas, el personal muy amable, está frente al Queen Victoria Building y puede tomarse metro, camión o tram caminando 2 min, catedral está a 3 cuadras y la zona nunca se queda sola, tienes súper enfrente por cualquier urgencia, puedes descansar super bien, no es un hotel de mochileros, me encantó

Reviewed on Oct 3, 2026

Kith Hotel Darling Harbour

Kith Hotel Darling Harbour

Pyrmont
$1,568
per person
Nov 5 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.8/10 Excellent! (527 reviews)
Teeny tiny room with bathroom surrounded with frosted glass within the room. Long walk from station.

Reviewed on Sep 25, 2026

The Darling at the Star

The Darling at the Star

Pyrmont
$2,327
per person
Dec 12 - Dec 17
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
9.6/10 Exceptional! (1,002 reviews)
Great!

Reviewed on Oct 3, 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

2 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.

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.

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.

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.

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

Bondi Beach

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

Woolooware Hotel Deals

Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
$264 nightly
$291 total
Oct 15 - Oct 16
Total with taxes and fees
9.6/10 Exceptional! (2,257 reviews)
"Location could not be beat but expected better service from a Four Seasons. Room was a bit cramped as well."

Reviewed on Oct 3, 2026

Four Seasons Hotel Sydney
Shangri-La Sydney

Shangri-La Sydney

176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
$197 nightly
$216 total
Oct 11 - Oct 12
Total with taxes and fees
9.2/10 Wonderful! (2,844 reviews)
"Clean, fantastic breakfast"

Reviewed on Oct 3, 2026

Shangri-La Sydney
Hyatt Regency Sydney

Hyatt Regency Sydney

161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
$161 nightly
$177 total
Oct 11 - Oct 12
Total with taxes and fees
Hyatt Regency Sydney
See all 5,776 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.

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

$267
per adult
Sydney Grand Tour by Helicopter
Sydney: Maroubra Surf Lesson

Sydney: Maroubra Surf Lesson

$75
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.