Woolloomooloo Vacations from $1,418

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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.
Central 2-bed With Parking & Stunning Views

Central 2-bed With Parking & Stunning Views

2.5 out of 5
Parramatta
Price was $1,760, price is now $1,418 per person
$1,418
per person
Mar 25 - Mar 30
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
No reviews
Quest Bella Vista

Quest Bella Vista

4 out of 5
Bella Vista
Price was $1,776, price is now $1,529 per person
$1,529
per person
Feb 22 - Feb 27
found 1 day ago
Roundtrip non-stop flight included
Seattle (SEA) to Sydney (SYD)
9/10 Wonderful! (646 reviews)
The greeting from the lady at check in was lovely & she explained everything clearly. The room was a connecting room & we could hear a lot of talking from next door, soundproofing was not great. The bed in our room was not very comfortable, it was a king bed but one side had a dip in it, could use a new mattress. The kitchen had a 2 burner cooktop, bar fridge & enough utensils for cooking. The bathroom was a bit tired but ok for us as it was just an overnight stay.

Reviewed on Dec 28, 2025

Fairlight 2-bed Apartment Steps From the Beach

Fairlight 2-bed Apartment Steps From the Beach

2.5 out of 5
Fairlight
Price was $2,073, price is now $1,616 per person
$1,616
per person
Mar 25 - Mar 30
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Sydney (SYD)
No reviews
3-bedroom Home in the Heart of Darlinghurst

3-bedroom Home in the Heart of Darlinghurst

2.5 out of 5
Darlinghurst
Price was $2,607, price is now $2,036 per person
$2,036
per person
Mar 6 - Mar 10
found 24 hours ago
Roundtrip flight included
New York (JFK) to Sydney (SYD)
No reviews
Beachfront Manly Apartment With Balcony & Parking

Beachfront Manly Apartment With Balcony & Parking

2.5 out of 5
Manly
Price was $2,317, price is now $1,853 per person
$1,853
per person
Mar 6 - Mar 10
found 24 hours ago
Roundtrip flight included
New York (JFK) 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
Sydney Town Hall featuring heritage architecture and a city

Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(1,320 area reviews)

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

Woolloomooloo Hotel Deals

Shangri-La Sydney

Shangri-La Sydney

5 out of 5
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
$185 nightly
The price is $204 total per night from Jan 11 to Jan 12
$204 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
9/10 Wonderful! (2,454 reviews)
Room view over Sydney harbour over opera house

Reviewed on Dec 30, 2025

Shangri-La Sydney
Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
$241 nightly
The price is $265 total per night from Jan 8 to Jan 9
$265 total
Jan 8 - Jan 9, 2026
Total with taxes and fees
9.6/10 Exceptional! (2,056 reviews)
Staff was most accommodating! Had a challenge at check in handled flawlessly.

Reviewed on Dec 29, 2025

Four Seasons Hotel Sydney
Hyatt Regency Sydney

Hyatt Regency Sydney

5 out of 5
161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
$164 nightly
The price is $180 total per night from Jan 9 to Jan 10
$180 total
Jan 9 - Jan 10, 2026
Total with taxes and fees
8.8/10 Excellent! (1,861 reviews)
Beautiful hotel, excellent location and amazing room

Reviewed on Dec 29, 2025

Hyatt Regency Sydney
See all 6,036 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.
All Inclusive Vacations
All Inclusive Vacations
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Beach Vacations
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Kid Friendly Vacations

Discover the most popular places to visit in Woolloomooloo

Woolloomooloo

Woolloomooloo Wharf

4.5/5(5 reviews)

Explore the waterfront in Sydney with a trip to Woolloomooloo Wharf. Stroll along the beautiful beaches or experience the acclaimed theater scene in this vibrant area.

Woolloomooloo Wharf
Lovely little spot for a great Chilli Dog or Pie whilst overlooking the bay

Harry’s Cafe de Wheels

4/5(1 review)

You can find out about the history of Sydney with a stop at Harry’s Cafe de Wheels. Discover the acclaimed art scene and shops in this vibrant area.

Harry’s Cafe de Wheels

Things to do

Sydney Opera House Tour & Meal + Drink at Opera Bar or House Canteen

Sydney Opera House Tour & Dine Experience

$59
per adult
96% of travellers recommend
Sydney Opera House Tour & Dine Experience
Sydney: Blue Mountains National Park Tour with River Cruise

Sydney: Blue Mountains National Park Tour with River Cruise

$66
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
Taronga Zoo Ticket with Sydney Harbour Ferry Return

Taronga Zoo Ticket with Sydney Harbour Ferry Return

$50
per adult
84% of travellers recommend
Taronga Zoo Ticket with Sydney Harbour Ferry Return
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.