Woollahra Vacations

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  • Plan, book, travel with confidence

  • Better together

    Save up to NT$5,067 when you book a flight and hotel together*

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

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Where to stay in Woollahra

Find the best Woollahra areas and neighborhoods for the activities you enjoy most. Learn more about Woollahra
Sydney Town Hall featuring heritage architecture and a city

Sydney Central Business District

1 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

Woollahra 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
The price is NT$5,535 per night from Dec 16 to Dec 17
NT$5,535
NT$6,089 total
Dec 16 - Dec 17
includes taxes & fees
9/10 Wonderful! (2,440 reviews)
Fantastic stay. Will definitely come back.

Reviewed on 2025/11/15

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
The price is NT$6,924 per night from Dec 16 to Dec 17
NT$6,924
NT$7,616 total
Dec 16 - Dec 17
includes taxes & fees
9.6/10 Exceptional! (2,012 reviews)
The room and staff were both exceptional. And the Mode restaurant was superb.

Reviewed on 2025/11/9

Four Seasons Hotel Sydney
View Sydney

View Sydney

4 out of 5
17 Blue Street North Sydney NSW
Fully refundableReserve now, pay when you stay
The price is NT$5,905 per night from Nov 23 to Nov 24
NT$5,905
NT$6,496 total
Nov 23 - Nov 24
includes taxes & fees
9/10 Wonderful! (1,192 reviews)
An outstanding location for easy access to the trains & ferries. Awesome view from the room of the Harbour Bridge. Excellent customer service & all very clean. Bed comfortable & good size room, but bathroom exceptionally compact. Unfortunately though as we are light sleepers we were very disturbed ...

Reviewed on 2025/11/14

View Sydney
See all 5,593 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.

Frequently asked questions

How much does a Woollahra vacation package cost?
Choose from any combination of flights, hotels and car rentals, and you can be vacationing in Woollahra from just . And the more you bundle, the more dollars you save. Your dream vacation has never been more affordable.
How do I get a cheap travel package to Woollahra?
Combine your bookings with Expedia to save big bucks on your next getaway. With more than 550 partner airlines and 1,000,000 hotels globally, your Woollahra vacation package can be tailored exactly to suit your budget. With all those extra dollars, why not include some interesting activities and tours? It's an easy way to unlock even more bargains. That vacation you've always dreamed of in Woollahra is closer than you thought!
Where should I stay in Woollahra?
Check Bondi Beach off your bucket list and then stay right around the corner. Soak up the exciting atmosphere around this major attraction and drop by whenever you please!
What are the top hotels in Woollahra?
The Hughenden Boutique Hotel is one of Woollahra's most sought-after properties. Reserve a room here and you can slumber peacefully knowing you're in excellent hands.
How far in advance should I book my Woollahra vacation?
It depends on the air carrier, but you can normally browse through international airfares on Expedia up to 12 months in advance. While it's a good idea to book ahead of time, lucky customers will occasionally nab a cheaper ticket just weeks prior to their intended journey.
What does an Expedia Woollahra travel package include?
Select from any combination of flights, hotels and rental cars. Once you've made your booking, you can add the fun stuff like experiences and tours. Want to pick your fare class? That's easily done too. The choice is all yours when it comes to creating your perfect Woollahra getaway.
What should I know before booking a Woollahra travel package?
You'll save big with an Expedia travel package. Bundle your airfares, rental cars and hotels and land fantastic discounts. Hotels aren't your only choice, however. Book with us and choose from beachside villas, creek-side mountain cabins and even houseboats and castles!
Can I choose my airline with a Woollahra Expedia vacation package?
You can, and with over 550 airlines to choose from across the globe, it's all about choice. Browse the available options and see which airline best fits your needs and budget.
If I'm not able to travel, can I cancel my Woollahra vacation package?
Yes, you can. We get that even the best-laid plans can go awry, so we're happy to help if you have to make changes to your Woollahra vacation package. You may be able to cancel or change your itinerary for free if you've booked within 24 hours. Your airline, hotel or car rental company may impose a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the nitty-gritty on change fees.

Discover the most popular places to visit in Woollahra

Circular Quay featuring general coastal views, modern architecture and a city

Circular Quay

4.5/5(1,399 reviews)

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

Circular Quay
Sydney Opera House showing a bay or harbor, modern architecture and a monument

Sydney Opera House

4.5/5(1,512 reviews)

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
Sydney Harbour Bridge showing night scenes, a bridge and a sunset

Sydney Harbour Bridge

4.5/5(1,379 reviews)

Stroll from end-to-end or climb to the top; either way, Sydney’s “Coat Hanger” serves up memories to last a lifetime.

Sydney Harbour Bridge
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.