Winston Hills Holidays from NZ$1,425
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Top Holiday Package Deals in Winston Hills
Price found within the past 48 hours. Click for updated prices.
The Old Clare by Ode Hotels
Chippendale
NZ$2,188
per person
3 Dec - 10 Dec
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
9.2/10 Wonderful! (592 reviews)
This was a last minute booking and I was able to book this smoothly within hours of checking in. The hotel is nicely located with a grocery store, pharmacy and restaurants within 3 minutes walking distance.
It is close to public transport - within walking distance on a main road to Central station, buses and light rail.
I had a room booked for 1 night which was clean, modern, with good amenities - robe, slippers, tea & coffee & various selections for the minibar. I utilized the kettle for my tea, appreciated this immensely! I ended up extending my stay for 4 nights - but switched rooms due to availability.
The only suggestion I have is for plugs to be upgraded to include USB/UBC outlets for easy charging ports near the bed and at the built in table. Upgraded lighting around the bathroom mirror would make a noticeable difference and I’m not sure there was a separate fan for the bathroom so got quite steamy during showering! All hotels I have stayed at for this price point have had a clear fan system for bathrooms.
Safe for solo travelers! Would stay here again.
Note ** The rooftop pool and bar were closed for the winter season so was unable to access these amenities despite the weather being warm and pleasant.
Reviewed on 5 Sept 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
3 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
1 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 Afterpay Arena or Accor Stadium 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.
Bondi Beach
1 out of top 10 points of interest in this area
Travellers to Bondi Beach praise its stunning beaches. If you've got some more time to explore, be sure to stop by Bondi Beach and Bondi Pavilion.
Our pick of the best Winston Hills Hotel Deals
Four Seasons Hotel Sydney
199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
NZ$527
25 Oct - 26 Oct
includes taxes & fees
9.6/10 Exceptional! (2,273 reviews)
"Everything was amazing, staff, amenities, room, view. Lounge."
Reviewed on 16 Oct 2026
Hyatt Regency Sydney
161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
NZ$365
1 Nov - 2 Nov
includes taxes & fees
9/10 Wonderful! (2,193 reviews)
"Great central location"
Reviewed on 16 Oct 2026
Shangri-La Sydney
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
NZ$397
25 Oct - 26 Oct
includes taxes & fees
9.2/10 Wonderful! (2,870 reviews)
"We had a great 14th wedding anniversary weekend with our eight-year-old daughter. The only criticism would be the double beds are a bit small for two adults but we could’ve got a bigger room just would’ve cost more level 36 is still as unreal as it always has been recommend to stay."
Reviewed on 16 Oct 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$1,425. 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$64
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
NZ$89
per adult
86% of travellers recommend
Sydney Opera House Official Guided Walking Tour
NZ$62
per adult
96% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.