Woollahra Holidays from £1,098

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to £335 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

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

    Rest easy

    Packages with flights are ATOL protected

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.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
per person
7 Nov - 11 Nov
found 1 day ago
Return flight included
Glasgow (GLA) to Sydney (SYD)
8.2/10 Very Good! (1,000 reviews)
Within walking distance to city transport. I had the standard single room which is quite small but adequate for 1 night.

Reviewed on 3 Aug 2025

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
per person
7 Nov - 11 Nov
found 1 day ago
Return flight included
Glasgow (GLA) to Sydney (SYD)
8.6/10 Excellent! (1,000 reviews)
Friendly staff, clean and convenient

Reviewed on 15 Aug 2025

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
per person
7 Nov - 11 Nov
found 1 day ago
Return flight included
Glasgow (GLA) to Sydney (SYD)
8.2/10 Very Good! (2,207 reviews)
Excellent location, just few mins walk to QVB, Townhall & Darling Harbour, lots of restaurants nearby. The room is a bit old, the towel rack had dropped in the washroom. Dun expect the kitchen could be used as the pot & pan are rusty & other food wares are also dirty so I didn’t cook. It’s still good value for money considered the location & room size.

Reviewed on 10 Aug 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
per person
7 Nov - 11 Nov
found 1 day ago
Return flight included
Glasgow (GLA) to Sydney (SYD)
9.4/10 Exceptional! (1,003 reviews)
The hotel was beautiful, but the common areas were open to the outside and cold. Lovely room, but the water pressure in the shower was very low. No free upgrade was offered. I was told one free bottle of wine per night with my VIP status. But I was given one cheap bottle of wine the first night and that was it - the wine was of such poor quality we did not ask for more. The staff was friendly and professional.

Reviewed on 10 Aug 2025

Coogee Bay Boutique Hotel

Coogee Bay Boutique Hotel

4 out of 5
Coogee
per person
7 Nov - 11 Nov
found 1 day ago
Return flight included
Glasgow (GLA) to Sydney (SYD)
8.8/10 Excellent! (824 reviews)
I loved my stay at this lovely boutique hotel near to my favorite Sydney beach. The hotel was tucked away on a street close to the beach and had a clean, modern ambience. Our room was spacious with an appealing decor. Would definitely stay here again.

Reviewed on 28 Jul 2025

Where to stay in Woollahra

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

Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(343 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

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 £135 per night from 14 Sept to 15 Sept
£135
14 Sept - 15 Sept
includes taxes & fees
8.8/10 Excellent! (2,351 reviews)
"Outstanding service. The front-of-house team was excellent. I had trouble ordering room service using the QR code. I will certainly be back. 10/10"

Reviewed on 12 Aug 2025

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 £171 per night from 24 Aug to 25 Aug
£171
24 Aug - 25 Aug
includes taxes & fees
9.6/10 Exceptional! (1,896 reviews)
"The hotel is beautifully presented and the staff are very professional and extremely friendly and helpful."

Reviewed on 11 Aug 2025

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 £129 per night from 15 Sept to 16 Sept
£129
15 Sept - 16 Sept
includes taxes & fees
8.8/10 Excellent! (1,774 reviews)
"good location and nice hotel. but some of the staff are not so nice"

Reviewed on 11 Aug 2025

Hyatt Regency Sydney
See all 5,404 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 £1,098, 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

Circular Quay showing general coastal views, a skyscraper and street scenes

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 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
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's Secret Bars Nightlife Tour

Sydney's Secret Bars Nightlife Tour

£32
per adult
100% of travellers recommend
Sydney's Secret Bars Nightlife Tour
Picture 11 for Activity Blue Mountains: Scenic World, Ferry, Zoo & Free Koala Photo

Blue Mountains Adventure: Scenic World, Zoo & Koala Photo

£107
per adult
88% of travellers recommend
Blue Mountains Adventure: Scenic World, Zoo & Koala Photo
Sydney Hop-On Hop-Off Big Bus Tour

Big Bus Sydney Hop-On Hop-Off Sightseeing Tour

£27
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour
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.