Woolloomooloo Vacations from $1,419

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Your Woolloomooloo Vacation

From its shopping to its bars and pubs and culture, there are loads of incredible reasons to book a vacation package to Woolloomooloo. When you want to escape from it all, this commercial neighborhood is calling. When it's time to see the sights, you'll find lots of awesome attractions nearby including University of Sydney, Sydney Cricket Ground and Hordern Pavilion. Tick off one or all during your trip to Woolloomooloo. Expedia is here to put your travel plans into action. Book your perfect Woolloomooloo vacation today.

The Latest Woolloomooloo Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Luxury 2-bed With Ocean Views and Garden

Luxury 2-bed With Ocean Views and Garden

Collaroy
$1,419
per person
Oct 18 - Oct 21
found 15 hours ago
Roundtrip non-stop flight included
Seattle (SEA) to Sydney (SYD)
No reviews
Spacious 3-bed Apartment in the Heart of St Ives

Spacious 3-bed Apartment in the Heart of St Ives

St Ives
$1,585
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Sydney (SYD)
No reviews
Relaxing Stay Near Fairlight's Scenic Spots

Relaxing Stay Near Fairlight's Scenic Spots

Fairlight
$1,425
per person
Oct 16 - Oct 21
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Sydney (SYD)
No reviews
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District
$1,496
per person
Nov 24 - Nov 28
found 15 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.2/10 Very Good! (2,897 reviews)
A great location, very handy to Darling Harbour and Town Hall station and all near by. Ideal for catching trains, buses or metro to get you around the city or just to Circular Quay. Having cooking facilities and fridge is a bonus to allow self catering to save costs, and Woolies just up the road. Good sized apartment with separate bedroom and bathroom. Some aspects of the room a little tired but more than good enough, and great pricing for central Sydney. Very attentive and friendly staff at check in and out.

Reviewed on Aug 29, 2026

Bright Stay in Sydney With Harbour Bridge Views

Bright Stay in Sydney With Harbour Bridge Views

Surry Hills
$1,515
per person
Oct 24 - Oct 29
found 12 hours ago
Roundtrip non-stop flight included
New York (NYC) to Sydney (SYD)
No reviews

Where to stay in Woolloomooloo

Find the best Woolloomooloo areas and neighborhoods for the activities you enjoy most. Learn more about Woolloomooloo
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 street with vintage buildings, pedestrians, and parked cars.

The Rocks

1 out of top 10 points of interest in this area

Historic area near Sydney's city center, The Rocks boasts close proximity to Circular Quay and Harbour Bridge views. Explore weekend Rocks Market, galleries, and historic pubs like Fortune of War, while enjoying walkable streets and easy rail access.

Woolloomooloo Hotel Deals

The Sydney Boulevard Hotel by Accor

The Sydney Boulevard Hotel by Accor

90 William Street Woolloomooloo NSW
Fully refundableReserve now, pay when you stay
$134 nightly
$147 total
Sep 6 - Sep 7
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"The view from the room was amazing and temp was easy to change. They did throw away my moisturizer and we did not get compensated."

Reviewed on Aug 20, 2026

The Sydney Boulevard Hotel by Accor
Shangri-La Sydney

Shangri-La Sydney

176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
$203 nightly
$223 total
Sep 6 - Sep 7
Total with taxes and fees
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
$92 nightly
$102 total
Sep 13 - Sep 14
Total with taxes and fees
8.2/10 Very Good! (2,900 reviews)
"A great location, very handy to Darling Harbour and Town Hall station and all near by. Ideal for catching trains, buses or metro to get you around the city or just to Circular Quay. Having cooking facilities and fridge is a bonus to allow self catering to save costs, and Woolies just up the road. ..."

Reviewed on Aug 29, 2026

YEHS Hotel Sydney Harbour Suites
See all 6,271 properties in Woolloomooloo
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 Woolloomooloo attractions

Woolloomooloo Wharf

9.0/10 (45 reviews)
Explore the waterfront in Sydney with a trip to Woolloomooloo Wharf. Stroll along the beautiful beaches or experience the fascinating museums in this vibrant area.
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Woolloomooloo Finger Wharf

Find out about the history of Sydney when you take a trip to Woolloomooloo Finger Wharf. Stroll along the beautiful beaches or experience the entertainment choices in this vibrant area.
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East Sydney Private Hospital

Though East Sydney Private Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Sydney while you are here.
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Harry’s Cafe de Wheels

8.8/10 (11 reviews)
You can find out about the history of Sydney with a stop at Harry’s Cafe de Wheels. Discover the acclaimed theater scene and shops in this vibrant area.
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Things to do

SYDNEY HARBOUR ALL-INCLUSIVE DINNER CRUISE

Sydney Harbour Dinner Cruise

$114
per adult
100% of travellers recommend
Sydney Harbour Dinner Cruise
Beautiful view of the Canberra in Australia

Canberra Discovery Tour - Australia's Capital by Gray Line Sydney

$122
per adult
72% of travellers recommend
Canberra Discovery Tour - Australia's Capital by Gray Line Sydney
Sydney Harbour BridgeMuseum - Day Session

Sydney Harbour BridgeMuseum - Day Session

$26
per adult
Sydney Harbour BridgeMuseum - Day Session
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.