Winston Hills Holidays from AU$679

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Your Winston Hills Holiday

Immerse yourself in all this neighbourhood has to offer with a tailor-made Winston Hills holiday package. However you imagine spending your days here, you'll find countless opportunities for fun, adventure and relaxation. Start your trip to Winston Hills with a visit to nearby attractions such as Westfield Parramatta Shopping Centre, CommBank Stadium and Parramatta Park. No matter your travel goals or budget, booking your ideal Winston Hills holiday has never been easier with Expedia.

Top Holiday Package Deals in Winston Hills

Price found within the past 48 hours. Click for updated prices.
Beautiful Bondi 1-bed Apartment Meters From Beach

Beautiful Bondi 1-bed Apartment Meters From Beach

2 out of 5
Bondi Beach
Save 100% on your flight
Price was AU$1,197, price is now AU$679 per person
AU$679
per person
11 Mar - 15 Mar
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
No reviews
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$1,790, price is now AU$976 per person
AU$976
per person
1 Apr - 8 Apr
found 24 hours ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.2/10 Very Good! (2,388 reviews)
Conveniently close to Darling Harbor. Friendly and helpful staff.

Reviewed on 21 Jan 2026

The Ultimo

The Ultimo

4 out of 5
Haymarket
Save 100% on your flight
Price was AU$1,321, price is now AU$724 per person
AU$724
per person
1 Apr - 8 Apr
found 24 hours ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.8/10 Excellent! (1,000 reviews)
Our stay at The Ultimo was great. Room was clean and comfortable, staff were friendly and the location is superb.

Reviewed on 15 Jan 2026

Bright 3-bed House With Garden,

Bright 3-bed House With Garden,

2.5 out of 5
Save 100% on your flight
Price was AU$2,336, price is now AU$1,321 per person
AU$1,321
per person
11 Mar - 18 Mar
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
No reviews

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 Town Hall featuring heritage architecture and a city

Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(8,551 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

Our pick of the best Winston Hills Hotel Deals

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 AU$424 per night from 1 Feb to 2 Feb
AU$424
1 Feb - 2 Feb
includes taxes & fees
9.6/10 Exceptional! (2,075 reviews)
Great staff and service!

Reviewed on 17 Jan 2026

Four Seasons Hotel Sydney
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 AU$334 per night from 1 Feb to 2 Feb
AU$334
1 Feb - 2 Feb
includes taxes & fees
9/10 Wonderful! (2,486 reviews)
We had a great stay at The Shangri-La hotel. All the staff were friendly & helpful. Our room was spotless, spacious & had great views of the bridge & opera house.

Reviewed on 18 Jan 2026

Shangri-La Sydney
Ace Hotel Sydney

Ace Hotel Sydney

5 out of 5
47 Wentworth Ave Sydney NSW
Fully refundableReserve now, pay when you stay
The price is AU$305 per night from 25 Jan to 26 Jan
AU$305
25 Jan - 26 Jan
includes taxes & fees
9.2/10 Wonderful! (834 reviews)
Can’t fault the location or the buzzing vibe. The rooms are extremely cute and very well designed. Would stay again.

Reviewed on 19 Jan 2026

Ace Hotel Sydney
See all 6,092 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Winston Hills holiday package cost?
Discover the best of Winston Hills from as little as AU$679. 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.

Discover the most popular places to visit in Winston Hills

Circular Quay showing street scenes, a city and a sunset

Circular Quay

4.5/5(4,882 reviews)

Under the gaze of the magnificent Opera House and Harbour Bridge, Sydney’s transport hub is a terminal of unexpected beauty.

Circular Quay
Sydney Opera House showing a bay or harbor, modern architecture and a monument

Sydney Opera House

4.5/5(3,486 reviews)

Take in a performance or just take in the splendour of one of the world’s most famous buildings.

Sydney Opera House
Sydney Harbour Bridge showing night scenes, a bridge and a sunset

Sydney Harbour Bridge

4.5/5(3,601 reviews)

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

Activities

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

AU$59
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

AU$40
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise

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

AU$85
per adult
88% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer 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.