Winston Hills Vacation Packages

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Top Holiday Package Deals in Winston Hills

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
8.2/10 Very Good! (2,195 reviews)
The front desk staff is very friendly and helpful. Very convenient and perfect location. Close to shopping Center and Chinatown. Surrounded by so many good restaurants. The only downside is our room is quite noisy and cant sleep specially during heavy traffic. I wish they have double glass windows to cut the traffic noise. On our second day the cleaner didn’t empty the rubbish and wash all the cups and mugs. Apart from that all good.

Reviewed on Aug. 4, 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
9.4/10 Exceptional! (1,004 reviews)
Really quirky hotel with friendly staff, good location, clean, comfortable and sizeable room

Reviewed on Jul. 28, 2025

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
8.6/10 Excellent! (1,002 reviews)
In centre of city with shops, transportation, culture & nightlife close by. Room was at rear of property overlooking an access road & looking onto another property. There is a common area to eat or relax but sometimes this was closed off due to meetings. Only way to access this area is via the lift as the corridor was used for left luggage. Staff were helpful & communication prior to stay. Front desk seemed always staffed which was beneficial as arrival was delayed by 15 hours due to cancelled flight.

Reviewed on Aug. 1, 2025

Pullman Quay Grand Sydney Harbour

Pullman Quay Grand Sydney Harbour

5 out of 5
Sydney Central Business District
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
9.2/10 Wonderful! (1,006 reviews)
It’s right on the quay,

Reviewed on Jul. 21, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
9/10 Wonderful! (579 reviews)
wonderful get away, five star experience. Breakfast is a must!

Reviewed on Jun. 24, 2025

Where to stay in Winston Hills

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

Winston Hills 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 $239 per night from Aug 17 to Aug 18
CA $239
CA $262 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (2,338 reviews)
"We enjoyed the large, comfortable rooms with large bathroom. Pillows weren't great, wouldve been nice to have aome options. We used the Horizon lounge, good selection of vegen food in the evening. Also had the pool to ourselves and enjoyed the spa. Reduced to 4* as not sure its value for money compared ..."

Reviewed on Aug. 3, 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 CA $282 per night from Aug 24 to Aug 25
CA $282
CA $310 total
Aug 24 - Aug 25
includes taxes & fees
9.6/10 Exceptional! (1,890 reviews)
"Stayed here recently and couldn’t be happier with the experience. The location was perfect, close to everything I needed, and the view from the room was stunning. The room itself was spotless, modern, and very comfortable - exactly what I was hoping for. From check-in to check-out, everything was ..."

Reviewed on Jul. 31, 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 CA $218 per night from Aug 17 to Aug 18
CA $218
CA $240 total
Aug 17 - Aug 18
includes taxes & fees
8.8/10 Excellent! (1,768 reviews)
"Location is ideal We return over. And over again Views from sky bar are to die for"

Reviewed on Jul. 31, 2025

Hyatt Regency Sydney
See all 5,449 properties in Winston Hills
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.
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Frequently asked questions

How much does a Winston Hills vacation package cost?
Discover the best of Winston Hills from as little as CA $1,900. Choose from a wonderful selection of flights, hotels and rental cars to suit every style and budget. Score even more discounts when you add a few experiences or tours to your package.
How do I get a cheap travel package to Winston Hills?
If you love amazing deals, combine your bookings into a Winston Hills vacation package. Whether you're searching for flights, hotels, rental cars or day tours, you can book everything in one place. You'll have loads of choice at your fingertips too. Expedia has more than 550 air carriers and 1,000,000 hotels throughout the world to take your pick of. Fly with who you prefer, stay in a place you like and save a pretty penny — now that's the perfect vacation!
Where should I stay in Winston Hills?
Stay at a hotel near Sydney Showground. This well-known attraction is in the heart of the action and on the to-do lists of many urban explorers.
How far in advance should I book my Winston Hills vacation?
While not all airlines release tickets early, you can usually compare international flights on Expedia up to a year in advance. This is the time you can score some incredible deals. If you're booking late, you may still be in luck. Sometimes the cheapest prices appear only weeks prior to departure.
What does an Expedia Winston Hills travel package include?
Flights, hotels and a cool car for all your fun road trip adventures. Simply mix and match your favorite bundle and get access to incredible deals. Once you've made your booking, add on a few tours and experiences and watch your savings grow. When it comes to creating your Winston Hills break, you're the boss!
What should I know before booking a Winston Hills travel package?
You'll save plenty with an Expedia travel package. Combine your airfares, rental cars and hotels and score exciting discounts. Hotels aren't your only choice, however. We've got beachfront villas, cozy city apartments and even houseboats and castles!
Can I choose my airline with a Winston Hills Expedia vacation package?
With a vacation package, you're always in charge. Whether you'd prefer to fly to Winston Hills in coach or business class, simply pick from the available airline options. Expedia has access to over 550 partner airlines across the world.
If I'm not able to travel, can I cancel my Winston Hills vacation package?
Because we understand life can throw you a few curveballs, the answer is yes. To find out more, check out our Customer Service Portal. But generally speaking, if you've booked your Winston Hills vacation package in the last 24 hours, you may be able to cancel or change it for no charge. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Winston Hills

Circular Quay featuring general coastal views, a sunset and central business district

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

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 Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

CA $46
per adult
84% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise

Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise

CA $73
per adult
88% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

CA $27
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
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.