Woolloomooloo Vacations from $1,358

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Mariners Court Hotel Sydney

Mariners Court Hotel Sydney

3.5 out of 5
Woolloomooloo
Price was $1,682, price is now $1,358 per person
$1,358
per person
Mar 3 - Mar 8
found 21 hours ago
Roundtrip non-stop flight included
Newark Liberty Intl. Airport (EWR) to Sydney (SYD)
8.4/10 Very Good! (1,003 reviews)
The room was fine but it’s fairly dated. Theres not really very good places to hang towels in the bathroom, the taps are old school individual hot and cold which have leaky washers and are over tightened. There’s no accessible power sockets near the bed, and the AC struggles to cool the room. There’s also only one small bin in the bathroom. Adding a mixer tap in the bathroom, cleaning up the bathroom storage, adding a dedicated bathroom towel. Looking at the AC and tying the bathroom exhaust to the light switch amd adding accessible power sockets would help bring the hotel up to the modern standard of others. In saying that the room was fine for a couple of nights and you can’t beat that location. The staff were also very helpful and accommodating.

Reviewed on Jan 8, 2026

Fairlight 2-bed Apartment Steps From the Beach

Fairlight 2-bed Apartment Steps From the Beach

2.5 out of 5
Fairlight
Price was $2,677, price is now $2,033 per person
$2,033
per person
Mar 31 - Apr 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sydney (SYD)
No reviews
APX Parramatta

APX Parramatta

4 out of 5
Rosehill
Price was $2,106, price is now $1,720 per person
$1,720
per person
Apr 3 - Apr 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Sydney (SYD)
7.4/10 Good! (1,001 reviews)
2 bedroom apartment was very spacious & very clean. Was only a one night stay for us, but the apartment appeared to have everything you would need for a longer stay. Beds were comfy, not much traffic noise at all despite being on a main road. Lots of car parks. Would definitely stay here again.

Reviewed on Dec 21, 2025

Chic 1-bed Apartment in the Heart of Newtown

Chic 1-bed Apartment in the Heart of Newtown

2.5 out of 5
Newtown
Price was $2,043, price is now $1,682 per person
$1,682
per person
Mar 31 - Apr 5
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sydney (SYD)
No reviews
APX Darling Harbour

APX Darling Harbour

3.5 out of 5
Sydney Central Business District
Price was $1,946, price is now $1,610 per person
$1,610
per person
Feb 13 - Feb 16
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sydney (SYD)
7.6/10 Good! (1,001 reviews)
Room was great, huge bed,location amazing but the men front of house, not that happy or helpful

Reviewed on Jan 6, 2026

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
$198 nightly
The price is $217 total per night from Feb 1 to Feb 2
$217 total
Feb 1 - Feb 2
Total with taxes and fees
9/10 Wonderful! (2,457 reviews)
We really enjoyed our stay at the Shangri- La, wonderful staff, all very helpful and service was prompt. The rooms were spacious and comfortable, really clean, everything you need at your fingertips. The Horizon Lounge was a highlight along with the food and views! Can’t beat the views .. perfect. ...

Reviewed on Jan 8, 2026

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
$227 nightly
The price is $250 total per night from Feb 1 to Feb 2
$250 total
Feb 1 - Feb 2
Total with taxes and fees
9.6/10 Exceptional! (2,067 reviews)
Clean room and very comfortable bed. Great views and location.

Reviewed on Jan 5, 2026

Four Seasons Hotel Sydney
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
252 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
$97 nightly
The price is $107 total per night from Jan 11 to Jan 12
$107 total
Jan 11 - Jan 12
Total with taxes and fees
8.2/10 Very Good! (2,481 reviews)
Lovely room nice staff and the right price

Reviewed on Jan 2, 2026

YEHS Hotel Sydney Harbour Suites
See all 6,080 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
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Woolloomooloo

Woolloomooloo

Woolloomooloo Wharf

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

You can find out about the history of Sydney with a stop at Harry’s Cafe de Wheels. Discover the entertainment choices 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
Sydney: Morning or Afternoon Harbour Sightseeing Cruise

Sydney: Morning or Afternoon Harbour Sightseeing Cruise

$37
per adult
94% of travellers recommend
Sydney: Morning or Afternoon Harbour Sightseeing Cruise
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.