Winston Hills Holidays from NZ$1,445
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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
Sydney Central Business District
NZ$1,988
per person
6 Nov - 13 Nov
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.2/10 Very good! (2,897 reviews)
A great location, very handy to Darling Harbour and Town Hall station and all near by. Ideal for catching trains, buses or metro to get you around the city or just to Circular Quay.
Having cooking facilities and fridge is a bonus to allow self catering to save costs, and Woolies just up the road.
Good sized apartment with separate bedroom and bathroom.
Some aspects of the room a little tired but more than good enough, and great pricing for central Sydney.
Very attentive and friendly staff at check in and out.
Reviewed on 29 Aug 2026
Our guide on 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
Sydney Central Business District
2 out of top 10 points of interest in this area
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.
Darling Harbour
The best place to get acquainted with Sidney's nautical passions – sailing, pleasure-boating, whale watching – or the Maritime Museum if you prefer dry land.
Sydney Olympic Park
2 out of top 10 points of interest in this area
Unique features of Sydney Olympic Park include the theatres and live music. Make a stop by Accor Stadium or Sydney Olympic Park Athletic Centre while you're exploring the area.
Manly
Venture to Sydney’s northern coast to explore this picturesque beach suburb, the perfect spot for surfing, shopping and sunbathing.
The Rocks
1 out of top 10 points of interest in this area
A noteworthy feature of The Rocks is its captivating waterfront views. While you're in town, be sure to stop and check out Circular Quay and Museum of Contemporary Art.
Our pick of the best Winston Hills Hotel Deals
Shangri-La Sydney
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
NZ$377
6 Sept - 7 Sept
includes taxes & fees
YEHS Hotel Sydney Harbour Suites
252 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
NZ$198
13 Sept - 14 Sept
includes taxes & fees
8.2/10 Very good! (2,900 reviews)
"A great location, very handy to Darling Harbour and Town Hall station and all near by. Ideal for catching trains, buses or metro to get you around the city or just to Circular Quay. Having cooking facilities and fridge is a bonus to allow self catering to save costs, and Woolies just up the road. ..."
Reviewed on 29 Aug 2026
Hyatt Regency Sydney
161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
NZ$326
13 Sept - 14 Sept
includes taxes & fees
9/10 Wonderful! (2,162 reviews)
"Good hotel"
Reviewed on 30 Aug 2026
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 Winston Hills holiday package cost?
Discover the best of Winston Hills from as little as NZ$1,445. 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 holiday 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 holiday!
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 holiday?
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 favourite 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, cosy city apartments and even houseboats and castles!
Can I choose my airline with a Winston Hills Expedia holiday package?
With a holiday 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 holiday 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 holiday 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.
Activities
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
NZ$61
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
NZ$76
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.