Woolloomooloo Holidays

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Price found within the past 48 hours. Click for updated prices.
  • Apartment | Reception
    Jun 18 - Jun 21

    Stylish 2-bed House With Private Courtyard + Flight

    Redfern
    3 nights
    2.5 star property
    10/10 - Exceptional (1 review)
    "Excellent place for us to use as a base for vivisting Sydney for a short holiday. 5-10min walk from Redfern railway station meaning it was easy to move around the city. "
    Reviewed May 5, 2026
    Return • Auckland (AKL) - Sydney (SYD)
    AKL - SYD • Direct SYD - AKL • Direct
    Save 100% on your flight
    NZ$1,992
    NZ$1,201
    per traveller
    found 1 day ago
    Stylish 2-bed House With Private Courtyard
  • Front of property
    Jul 19 - Jul 26

    YEHS Hotel Sydney CBD + Flight

    Sydney Central Business District
    7 nights
    3.5 star property
    8.2/10 - Very good (1,006 reviews)
    "Centrally located. We love the location. Also the staff are helpful."
    Reviewed May 17, 2026
    Return • Christchurch (CHC) - Sydney (SYD)
    CHC - SYD • Direct SYD - CHC • Direct
    Save 100% on your flight
    NZ$2,339
    NZ$1,348
    per traveller
    found 1 day ago
    YEHS Hotel Sydney CBD
  • Apartment | Living area
    Jul 31 - Aug 5

    Huge Harbour View Apartment In Historic Home + Flight

    Cremorne
    5 nights
    2.5 star property
    Return • Auckland (AKL) - Sydney (SYD)
    AKL - SYD • Direct SYD - AKL • Direct
    Save 100% on your flight
    NZ$2,665
    NZ$1,558
    per traveller
    found 1 day ago
    Huge Harbour View Apartment In Historic Home
  • Apartment | Pool
    Jun 20 - Jun 24

    Modern CBD Aparment, Workspace, Fast Wifi and Pool + Flight

    Sydney Central Business District
    4 nights
    2.5 star property
    Return • Auckland (AKL) - Sydney (SYD)
    AKL - SYD • Direct SYD - AKL • Direct
    Save 100% on your flight
    NZ$2,094
    NZ$1,232
    per traveller
    found 1 day ago
    Modern CBD Aparment, Workspace, Fast Wifi and Pool
  • Apartment | Private kitchen
    Jul 19 - Jul 26

    Cosy Studio With City Views + Flight

    Darlinghurst
    7 nights
    2.0 star property
    Return • Christchurch (CHC) - Sydney (SYD)
    CHC - SYD • Direct SYD - CHC • Direct
    Save 100% on your flight
    NZ$2,298
    NZ$1,408
    per traveller
    found 1 day ago
    Cosy Studio With City Views

Our guide on where to stay in Woolloomooloo

Find the best Woolloomooloo areas and neighborhoods for the activities you enjoy most. Learn more about Woolloomooloo
Sydney Central Business District

Sydney Central Business District

3 out of top 10 points of interest in this area
4.5/5(8,638 area reviews)

Known for its captivating waterfront views and popular shops, there's plenty to explore in Sydney Central Business District. Check out top attractions like Circular Quay and Sydney Opera House, and jump on the metro at Martin Place Station or St. James Station to see more of the city.

Find hotels in Sydney Central Business District

Our pick of the best Woolloomooloo Hotel Deals

The Sydney Boulevard Hotel by Accor

The Sydney Boulevard Hotel by Accor

4 out of 5
90 William Street Woolloomooloo NSW
Fully refundableReserve now, pay when you stay
The price is NZ$231 per night from 14 June to 15 June
NZ$231
14 June - 15 June
includes taxes & fees
8.8/10 Excellent! (1,003 reviews)
"My parents really enjoyed their stay. Very comfortable, clean and the hotel is in a great location in the city."

Reviewed on 14 May 2026

The Sydney Boulevard Hotel by Accor
Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
The price is NZ$433 per night from 24 May to 25 May
NZ$433
24 May - 25 May
includes taxes & fees
9.6/10 Exceptional! (2,180 reviews)
"Booked a Harbour View Club Suite with access to the Level 32 Exec Club. Access to the Club made a huge difference, and made the stay good value as, inclusive breakfast, lunch, canapés (much more than just canapés), drinks, wine, beer and cocktails were very good. My wife is Gluten Free and Dairy ..."

Reviewed on 19 May 2026

Four Seasons Hotel Sydney
Shangri-La Sydney

Shangri-La Sydney

5 out of 5
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
The price is NZ$409 per night from 24 May to 25 May
NZ$409
24 May - 25 May
includes taxes & fees
9.2/10 Wonderful! (2,685 reviews)
"The staff were more than helpful breakfast was lovely as was the service for high tea Jane was very accommodating and professional"

Reviewed on 19 May 2026

Shangri-La Sydney
See all 6,078 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.

Frequently asked questions

How much does a Woolloomooloo holiday package cost?
Starting from as little as , you can custom build your Woolloomooloo package. Simply combine hotels, flights and car rentals and be rewarded with discounts.
How do I get a cheap travel package to Woolloomooloo?
Just think of all the fabulous things you could do in Woolloomooloo with extra cash in your wallet. Watch your savings stack up when you combine your travel bookings into a Woolloomooloo holiday package. You have loads of choice when you book your trip with Expedia too. In fact, you can select from over 550 air carriers and 1 000 000 properties worldwide. Whether you're heading off with the family or travelling with someone special, organising a getaway to Woolloomooloo is better with a package.
Where should I stay in Woolloomooloo?
With lots to explore in Woolloomooloo, it'd be handy for you to book a hotel near its attractions. St Vincent's Hospital, The Domain and Crown Street are some top ones to put on your itinerary.
What are the top hotels in Woolloomooloo?
Reserve a room at OMalleys Hotel. It's one of this neighbourhood's most popular properties. Another reputable option in Woolloomooloo is East Sydney Hotel.
How far in advance should I book my Woolloomooloo holiday?
Reward yourself with the biggest variety at the cheapest prices by booking your Woolloomooloo adventure nice and early. Airlines typically release flight tickets around a year before departure, so reserve your spot ASAP. That being said, Expedia is dedicated to providing you with the best bargains around, so there's never a bad time to book your dream holiday!
What does an Expedia Woolloomooloo travel package include?
That depends on what you want. If you're travelling by yourself, you might decide to bundle hotels and flights. Taking the entire family to Woolloomooloo? A travel package that includes flights, hotels and rental cars might be a better fit. Expedia gives you the freedom to build your own travel package.
What should I know before booking a Woolloomooloo travel package?
Whether it's relaxation or adventure you're craving, a Woolloomooloo holiday package lets you organise your escape your way. Plus, you'll get access to great discounts when you combine your accommodation with your flights and rental car. The more you bundle, the more you'll save!
Can I choose my airline with a Woolloomooloo Expedia holiday package?
Yes — that's one of the best things about an Expedia holiday package. You can mix and match your flights, hotels and more. We have more than 550 airline partners worldwide, so you have loads of choice when organising your Woolloomooloo adventure.
If I'm not able to travel, can I cancel my Woolloomooloo holiday package?
Whether it's your flight or hotel, you can cancel or amend it. Booked your Woolloomooloo holiday package in the last 24 hours? You may be able to make changes or cancellations at no cost. For older bookings, you may be charged a fee by your airline, hotel or car rental company. For further information, browse our Customer Service Portal. We'll help you each step of the way.

Discover the most popular places to visit in Woolloomooloo

Harry’s Cafe de Wheels

4.5/5(8 reviews)

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

Harry’s Cafe de Wheels

Activities

Sydney Hop-On Hop-Off Big Bus Tour

Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

NZ$77
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

NZ$62
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

NZ$395
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
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.