Woollahra Vacations

Book a Hotel + Flight or Car together to unlock savings

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  • Better together

    Save up to ¥109,000 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
Price found within the past 48 hours. Click for updated prices.
  • Aug 5 - Aug 10

    Spacious Stay Near Shops & Cafes in Marrickville + Flight

    Marrickville
    3 nights
    2.5 star property
    Roundtrip Tokyo (HND) - Sydney (SYD)
    HND - SYD1 stop SYD - HND1 stop
    ¥266,333
    ¥191,367
    per traveler
    found 1 day ago
    Spacious Stay Near Shops & Cafes in Marrickville
  • Aug 1 - Aug 8

    Modern 1-bed With Tamarama Beach Views + Flight

    Tamarama
    7 nights
    2.0 star property
    Roundtrip Tokyo (HND) - Sydney (SYD)
    HND - SYD1 stop SYD - HND1 stop
    Save 100% on your flight
    ¥397,725
    ¥251,208
    per traveler
    found 1 day ago
    Modern 1-bed With Tamarama Beach Views
  • Aug 1 - Aug 8

    Huge Harbour View Apartment In Historic Home + Flight

    Cremorne
    7 nights
    2.5 star property
    Roundtrip Tokyo (HND) - Sydney (SYD)
    HND - SYD1 stop SYD - HND1 stop
    Save 100% on your flight
    ¥370,656
    ¥234,936
    per traveler
    found 1 day ago
    Huge Harbour View Apartment In Historic Home
  • Aug 1 - Aug 8

    YEHS Hotel Sydney Harbour Suites + Flight

    Sydney Central Business District
    7 nights
    4.0 star property
    8.2/10 - Very Good (2,738 reviews)
    "We have stayed in hundreds of hotels and serviced apartments and this hotel is by far the worst experience we have ever had at any property. The unit we were given was generally in rather poor condition due to a lack of maintenance. The floor was filthy, the drawers and shelves appeared to have not been cleaned or even dusted for months, and in general, the entire unit can only be described as tattered and dirty. Since we only booked two nights, we decided to just wipe down the drawers and..."
    Reviewed May 22, 2026
    Roundtrip Tokyo (HND) - Sydney (SYD)
    HND - SYD1 stop SYD - HND1 stop
    ¥282,200
    ¥196,960
    per traveler
    found 1 day ago
    YEHS Hotel Sydney Harbour Suites
  • Aug 11 - Aug 16

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

    Sydney Central Business District
    4 nights
    2.5 star property
    Roundtrip Osaka (KIX) - Sydney (SYD)
    KIX - SYD1 stop SYD - KIX1 stop
    ¥311,290
    ¥220,849
    per traveler
    found 10 hours ago
    Modern CBD Aparment, Workspace, Fast Wifi and Pool

Where to stay in Woollahra

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

Woollahra Hotel Deals

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 ¥35,146 per night from May 31 to Jun 1
¥35,146
¥38,661 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (2,175 reviews)
"Excellent staff at every level and exceptional comfort."

Reviewed on May 21, 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 ¥34,630 per night from May 24 to May 25
¥34,630
¥38,094 total
May 24 - May 25
includes taxes & fees
9.2/10 Wonderful! (2,681 reviews)
"Great property to visit with young adult. Great location..."

Reviewed on May 22, 2026

Shangri-La 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 ¥30,908 per night from May 31 to Jun 1
¥30,908
¥33,999 total
May 31 - Jun 1
includes taxes & fees
9/10 Wonderful! (2,044 reviews)
"Great location. Views from zephyr bar were stunning"

Reviewed on May 22, 2026

Hyatt Regency Sydney
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.