Woollahra Vacation Packages

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Top Holiday Package Deals in Woollahra

Price found within the past 48 hours. Click for updated prices.
Haven Glebe

Haven Glebe

4.5 out of 5
Glebe
Price was CA $2,309, price is now CA $2,135 per person
CA $2,135
per person
Oct 31 - Nov 2
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sydney (SYD)
8.8/10 Excellent! (950 reviews)
Good location for Sydney. 25 min walk to Darling harbour or short bus ride to central/ circular quay. Hotel was nice, clean, quiet. Good gym.

Reviewed on Aug. 8, 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Price was CA $2,644, price is now CA $2,279 per person
CA $2,279
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sydney (SYD)
8.2/10 Very Good! (1,000 reviews)
Small room, good for short stay, reasonable walk to L2/3 on George St.

Reviewed on Aug. 20, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was CA $2,654, price is now CA $2,316 per person
CA $2,316
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sydney (SYD)
9/10 Wonderful! (581 reviews)
Quiet and convenient.

Reviewed on Aug. 23, 2025

Coogee Bay Boutique Hotel

Coogee Bay Boutique Hotel

4 out of 5
Coogee
Price was CA $2,732, price is now CA $2,446 per person
CA $2,446
per person
Nov 11 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Sydney (SYD)
8.8/10 Excellent! (827 reviews)
Great location. Spacious, clean room with a beautiful view. Everything within walking distance. Plenty of food options around. The beach is right across the street

Reviewed on Aug. 16, 2025

Harbourside 31 in Mcmahons Point

Harbourside 31 in Mcmahons Point

2 out of 5
McMahons Point
Price was CA $2,583, price is now CA $2,460 per person
CA $2,460
per person
Oct 31 - Nov 2
found 22 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sydney (SYD)
No reviews

Where to stay in Woollahra

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

2 out of top 10 points of interest in this area
4.5/5(381 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 CA $236 per night from Sep 7 to Sep 8
CA $236
CA $260 total
Sep 7 - Sep 8
includes taxes & fees
8.8/10 Excellent! (2,364 reviews)
Was okay not exceptional
"Was okay not exceptional. Before arriving contacted hotel for a request no response. Very disappointed with the club lounge. Club lounge- cramped. Everyone handling wine bottles if you wanted other drinks you had to search for menu then cram in a corner to get servers. Food was VERY limited nothing ..."

Reviewed on Aug. 24, 2025

Shangri-La Sydney
The Fullerton Hotel Sydney

The Fullerton Hotel Sydney

5 out of 5
1 Martin Place, Sydney, NSW
Fully refundableReserve now, pay when you stay
The price is CA $279 per night from Sep 7 to Sep 8
CA $279
CA $308 total
Sep 7 - Sep 8
includes taxes & fees
9.2/10 Wonderful! (2,499 reviews)
"Fantastic experience...everything we could have asked for"

Reviewed on Aug. 24, 2025

The Fullerton Hotel 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 CA $323 per night from Sep 14 to Sep 15
CA $323
CA $355 total
Sep 14 - Sep 15
includes taxes & fees
9.6/10 Exceptional! (1,920 reviews)
"Great location in the rocks, walkable to the Sydney opera house, harbor bridge and botanical gardens. Our room was spacious and we had great views (floor 21). Our kids loved the heated pool and hot tub. We didn’t eat in the hotel but can highly recommend the 4 seasons."

Reviewed on Aug. 18, 2025

Four Seasons Hotel Sydney
See all 5,303 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 Vacations
All Inclusive Vacations
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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 CA $2,135. 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, a sunset and central business district

Circular Quay

4.5/5(424 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

Sydney Opera House

4.5/5(446 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

Sydney Harbour Bridge

4.5/5(411 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

Things to do

Sydney's Secret Bars Nightlife Tour

Sydney's Secret Bars Nightlife Tour

CA $58
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

CA $197
per adult
88% of travellers recommend
Blue Mountains Adventure: Scenic World, Zoo & Koala Photo
Sydney: Blue Mountains National Park Tour with River Cruise

Sydney: Blue Mountains National Park Tour with River Cruise

CA $89
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
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.