Woollahra Vacations

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    Save up to ￥109,000 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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Price found within the past 48 hours. Click for updated prices.
  • Apartment | Pool | Outdoor pool
    Jul 29 - Aug 3

    Sleek 1-bed by Jubilee Park With Pool + Flight

    Parramatta
    5 nights
    2.5 star property
    4.0/10 - (1 review)
    "The water was super cold in winter"
    Reviewed April 25, 2026
    Roundtrip • Tokyo (HND) - Sydney (SYD)
    HND - SYD • 1 stop SYD - HND • 1 stop
    ￥434,367
    ￥209,165
    per traveler
    found 2 hours ago
    Sleek 1-bed by Jubilee Park With Pool
  • Apartment | Living room
    Jul 15 - Jul 19

    Spacious 3-bed Home in Princeton Pearl Double Bay + Flight

    Double Bay
    3 nights
    2.0 star property
    Roundtrip • Tokyo (NRT) - Sydney (SYD)
    NRT - SYD • 1 stop SYD - NRT • 1 stop
    ￥673,308
    ￥287,559
    per traveler
    found 1 day ago
    Spacious 3-bed Home in Princeton Pearl Double Bay
  • Apartment | Outdoor dining
    Aug 9 - Aug 15

    Apartment With Pool Access, a Minute to the Beach + Flight

    Manly
    5 nights
    2.5 star property
    Roundtrip • Tokyo (NRT) - Sydney (SYD)
    NRT - SYD • 1 stop SYD - NRT • 1 stop
    ￥541,521
    ￥255,601
    per traveler
    found 12 hours ago
    Apartment With Pool Access, a Minute to the Beach
  • Apartment | Living room
    Jul 15 - Jul 19

    Central 2-bed With Parking & Stunning Views + Flight

    Parramatta
    3 nights
    2.5 star property
    Roundtrip • Tokyo (NRT) - Sydney (SYD)
    NRT - SYD • 1 stop SYD - NRT • 1 stop
    Save 100% on your flight
    ￥527,175
    ￥250,734
    per traveler
    found 1 day ago
    Central 2-bed With Parking & Stunning Views
  • Apartment | Living room
    Jul 15 - Jul 19

    2-bed Apartment Near Manly Beach + Flight

    Manly
    3 nights
    2.5 star property
    Roundtrip • Tokyo (NRT) - Sydney (SYD)
    NRT - SYD • 1 stop SYD - NRT • 1 stop
    ￥451,869
    ￥230,739
    per traveler
    found 1 day ago
    2-bed Apartment Near Manly Beach

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(1,344 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 ￥34,364 per night from Jun 15 to Jun 16
￥34,364
￥37,801 total
Jun 15 - Jun 16
includes taxes & fees
9.2/10 Wonderful! (2,726 reviews)
"Excellent staffs, services, good location and amazing view of Opera house from the room."

Reviewed on Jun 9, 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
The price is ￥37,031 per night from Jun 23 to Jun 24
￥37,031
￥40,734 total
Jun 23 - Jun 24
includes taxes & fees
9.6/10 Exceptional! (2,216 reviews)
"The staff were amazing, could not do enough for you. Exceptional"

Reviewed on Jun 9, 2026

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
The price is ￥30,671 per night from Jun 14 to Jun 15
￥30,671
￥33,738 total
Jun 14 - Jun 15
includes taxes & fees
9/10 Wonderful! (2,072 reviews)
"So very disappointed TV was not working no hiar dryer no fan in bathroom services was terrible will not go there 😢 should get a refund"

Reviewed on Jun 8, 2026

Hyatt Regency Sydney
See all 6,151 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.