Woollahra Holidays

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Your Woollahra Holiday

Organising your next travel adventure just got a whole lot simpler with a holiday package to Woollahra. Experience the best this neighbourhood has to offer while making beautiful memories you'll treasure. When it's time to head out and explore, you'll find lots of top attractions nearby including Sydney Opera House, Sydney Harbour Bridge and Bondi Beach. Tick off one, two or all during your trip to Woollahra. Expedia will help you turn your ideal Woollahra holiday into reality, no matter your budget or travel plans.

Price found within the past 48 hours. Click for updated prices.
  • Restaurant
    Jun 25 - Jul 5

    YEHS Hotel Sydney Harbour Suites + Flight

    Sydney Central Business District
    9 nights
    4.0 star property
    8.2/10 - Very good (2,746 reviews)
    "A spacious one bedroom unit. An older building, but has all the features you need. Very central. Short walk to town hall trains . Walk over a overbridge to Darling Harbour."
    Reviewed May 26, 2026
    Return • London (LHR) - Sydney (SYD)
    LHR - SYD • 1 stop SYD - LHR • 1 stop
    £1,938
    £1,426
    per traveller
    found 1 day ago
    YEHS Hotel Sydney Harbour Suites
  • Apartment | Beach
    Aug 1 - Aug 15

    Bright 2-bed Flat With Balcony in Vaucluse + Flight

    Vaucluse
    12 nights
    2.5 star property
    Return • Birmingham (BHX) - Sydney (SYD)
    BHX - SYD • 1 stop SYD - BHX • 1 stop
    £3,284
    £2,406
    per traveller
    found 2 days ago
    Bright 2-bed Flat With Balcony in Vaucluse
  • Apartment | Living room
    Aug 1 - Aug 15

    Central 2-bed Apartment With Private Parking + Flight

    Strathfield
    12 nights
    2.0 star property
    10/10 - Exceptional (1 review)
    "Great appartment with brilliant amenities. Would highly recommended this as a place to stay."
    Reviewed April 12, 2026
    Return • Birmingham (BHX) - Sydney (SYD)
    BHX - SYD • 1 stop SYD - BHX • 1 stop
    £3,007
    £2,279
    per traveller
    found 2 days ago
    Central 2-bed Apartment With Private Parking
  • Terrace/patio
    Jul 12 - Jul 26

    The Old Clare by Ode Hotels + Flight

    Chippendale
    12 nights
    4.5 star property
    9.2/10 - Wonderful (570 reviews)
    "Beautiful and characterful room, very spacious, located in a great area."
    Reviewed May 15, 2026
    Return • London (LGW) - Sydney (SYD)
    LGW - SYD • 1 stop SYD - LGW • 1 stop
    £2,394
    £1,843
    per traveller
    found 1 day ago
    The Old Clare by Ode Hotels
  • Indoor pool, open 6:00 AM to 10:00 PM, pool loungers
    Jul 12 - Jul 26

    Rydges Sydney Central + Flight

    Surry Hills
    12 nights
    4.5 star property
    8.8/10 - Excellent (1,007 reviews)
    "Great location with Brewery next door"
    Reviewed May 24, 2026
    Return • London (LGW) - Sydney (SYD)
    LGW - SYD • 1 stop SYD - LGW • 1 stop
    £2,100
    £1,665
    per traveller
    found 1 day ago
    Rydges Sydney Central

Where to stay in Woollahra

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

Sydney Central Business District

3 out of top 10 points of interest in this area
4.5/5(345 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

Top hotels in Woollahra

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 £181 per night from 31 May to 1 Jun
£181
31 May - 1 Jun
includes taxes & fees
9.6/10 Exceptional! (2,183 reviews)
"Excellent location…………………"

Reviewed on 25 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 £178 per night from 8 Jun to 9 Jun
£178
8 Jun - 9 Jun
includes taxes & fees
9.2/10 Wonderful! (2,691 reviews)
"The reception is pure chaos with 50+ people in there most of the time. There are almost always people sleeping in the coffee shop and then because it’s not maximalist enough, there’s an art gallery with a million different works on display. The rooms are large, but look very tired and dated. The ..."

Reviewed on 26 May 2026

Shangri-La 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
The price is £82 per night from 21 Jun to 22 Jun
£82
21 Jun - 22 Jun
includes taxes & fees
8.2/10 Very Good! (2,746 reviews)
"A spacious one bedroom unit. An older building, but has all the features you need. Very central. Short walk to town hall trains . Walk over a overbridge to Darling Harbour."

Reviewed on 26 May 2026

YEHS Hotel Sydney Harbour Suites
See all 6,050 properties in Woollahra
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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Woollahra travel package cost?
Starting from just , a travel package is your portal to cheap travel. Custom make your Woollahra adventure by picking from our huge range of airfares, hotels and rental cars.
If I'm not able to travel, can I cancel my Woollahra travel package?
Don't worry if you're rethinking your Woollahra travel package — you can cancel or change your booking. And if you've booked it within 24 hours, you may be able to do it for free. However, bookings made more than 24 hours ago may incur a fee from your airline, hotel or car rental company. We get that life can sometimes throw you a curveball, so make your way to our Customer Service Portal if that occurs. When you're ready to make changes, we'll take care of it.
How do I get a cheap travel package to Woollahra?
Bundling your flight and hotel with Expedia won't just save valuable time — it'll save you cash too. A Woollahra travel package makes it a cinch to create your perfect trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule won't be hard. Not only that, we've got over 1,000,000 hotels globally to take your pick of. Now that's what we call choice. Whatever your budget, Expedia can show you the world.
Does Expedia offer Book Now, Pay Later Woollahra holidays?
We certainly do. Expedia has joined forces with online lender Klarna to help you conveniently pay for your trip in manageable instalments. Simply choose the payment plan that suits you best during the checkout process and take the stress out of budgeting for your next trip. Remember to bundle your accommodation, flights and car hire with Expedia to get the biggest bang for your holiday buck. Check out our flexible payment options below:

  • Pay monthly holidays: Realise your holiday dreams sooner with Klarna's easy monthly instalment plans. If paying just a small amount each month works for you, pick this option during the checkout process.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna allows you to pay for your holiday in multiple transactions.
  • Low deposit holidays: Clicking on the "book now" button is easier with this option. Simply put down a small deposit on your booking and then start packing your bags.

Where should I stay in Woollahra?
A journey to Woollahra isn't complete without seeing Sydney Opera House and Bondi Beach. Stay as close as possible for quick access to these impressive attractions.
What are the top hotels in Woollahra?
Get your trip off to a flying start by booking a stay at Sheraton Grand Sydney Hyde Park. It's one of most popular properties in Woollahra. Another welcoming option is Hyatt Regency Sydney.
How far in advance should I book my Woollahra holiday?
Get rewarded with the biggest variety at the lowest prices by booking your adventure to Woollahra nice and early. Air carriers usually sell flights around 12 months before departure, so secure your spot as soon as you can. That being said, Expedia is dedicated to giving you the best deals around, so it's never a bad time to book your dream holiday!
What does an Expedia Woollahra travel package include?
Car rentals, flights and hotels — we connect you to the best deals. All you'll have to do is pick and choose your favourite combination. Once you've made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to put together an amazing Woollahra trip.
What should I know before booking a Woollahra travel package?
A travel package can be customized for your budget and is a terrific way to make your money go further. What you include is your call. Rental cars, hotels and flights — choose any combination that suits your style.
Can I choose my airline with a Woollahra Expedia travel package?
Yes — and it's easy too. Expedia has access to more than 550 partner airlines all over the world. Our travel packages give you the freedom to pick from available flight, hotel or activity options that fit your needs.

Popular places to visit

Sydney Opera House

Sydney Opera House

One of the world’s most famous buildings is surprisingly accessible; take in a show or just take a stroll to admire this astonishing building.

Sydney Opera House
Circular Quay

Circular Quay

Flanked by the Opera House and Harbour Bridge, Sydney’s transportation hub is one of the prettiest terminals in the world.

Circular Quay
Sydney Harbour Bridge

Sydney Harbour Bridge

An iconic structure on a beautiful harbour with breath-taking views at any time of day or night. Climb it, walk it, photograph it or just stand back and admire it.

Sydney Harbour Bridge

Things to do

Sydney Opera House Official Guided Walking Tour

Sydney Opera House Official Guided Walking Tour

£27
per adult
96% of travellers recommend
Sydney Opera House Official Guided Walking Tour
Sydney Harbour Cultural Cruise with Island Stop

Sydney Harbour Cultural Cruise with Island Stop

£44
per adult
Sydney Harbour Cultural Cruise with Island Stop
Sydney Harbour Discovery Cruise Including Lunch

Sydney Harbour Discovery Cruise Including Lunch

£42
per adult
96% of travellers recommend
Sydney Harbour Discovery Cruise Including Lunch
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. Flight-inclusive packages are ATOL protected.