Winston Hills Holidays from AU$520

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to AU$2,500 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

Sydney Central Business District
Save 100% on your flight
AU$520
per person
28 Oct - 30 Oct
found 17 hours ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.4/10 Very good! (1,004 reviews)
2-bed Harbourside Home With Views in Fab Location

2-bed Harbourside Home With Views in Fab Location

McMahons Point
AU$1,105
per person
23 Sept - 29 Sept
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
No reviews
Chic Unit With Rooftop Terrace Near Sights & Shops

Chic Unit With Rooftop Terrace Near Sights & Shops

Pyrmont
Save 100% on your flight
AU$1,047
per person
3 Nov - 8 Nov
found 9 hours ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
No reviews
Ground Floor Spacious Home in Kiama's Heart

Ground Floor Spacious Home in Kiama's Heart

Save 100% on your flight
AU$1,112
per person
1 Oct - 5 Oct
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
No reviews
Bright & Spacious 1-bed in Vibrant Sydney

Bright & Spacious 1-bed in Vibrant Sydney

Sydney Central Business District
Save 100% on your flight
AU$585
per person
18 Sept - 21 Sept
found 19 hours ago
Return flight included
Melbourne (MEL) 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
A historic clock tower with a modern skyscraper in the background.

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.

Find hotels in Sydney Central Business District
A nighttime cityscape with illuminated buildings reflecting on the water.

Darling Harbour

Once the site of disused railway yards and dilapidated wharves, one of Sydney’s greatest urban renewal projects has breathed life into this location once more.

Find hotels in Darling Harbour
A street with vintage buildings, pedestrians, and parked cars.

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.

Find hotels in The Rocks
A large, arched building with multiple entry points, including signs for 'Entry' and 'No entry'.

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.

Find hotels in Sydney Olympic Park
A crowded beach with people sunbathing and swimming, surrounded by buildings and trees.

Manly

This coastal suburb of Sydney is like something from a postcard, and a haven for surfers, swimmers and sunbakers.

Find hotels in Manly

Our pick of the best Winston Hills Hotel Deals

Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
AU$378
6 Sept - 7 Sept
includes taxes & fees
9.6/10 Exceptional! (2,260 reviews)
"."

Reviewed on 9 Aug 2026

Four Seasons Hotel Sydney
Shangri-La Sydney

Shangri-La Sydney

176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
AU$319
6 Sept - 7 Sept
includes taxes & fees
Shangri-La Sydney
Hyatt Regency Sydney

Hyatt Regency Sydney

161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
AU$299
16 Aug - 17 Aug
includes taxes & fees
9/10 Wonderful! (2,126 reviews)
"The staff are very polite, and go out of their way to help.,From first greeting onwards. The breakfast in the morning is excellent. The staff at the breakfast simply superb people. Thank you so much."

Reviewed on 10 Aug 2026

Hyatt Regency Sydney
See all 6,242 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
family friendly holidays
Family Friendly Holidays
Family Friendly Holidays
golf holidays
Golf Holidays
Golf Holidays
luxury holidays
Luxury Holidays
Luxury Holidays
romantic holidays
Romantic Holidays
Romantic Holidays
ski holidays
Ski Holidays
Ski Holidays
honeymoon holidays
Honeymoon Holidays
Honeymoon Holidays
pet friendly holidays
Pet-friendly Holidays
Pet-friendly Holidays
Spa Holidays
Spa Holidays
Spa Holidays

Frequently asked questions

How much does a Winston Hills holiday package cost?
Discover the best of Winston Hills from as little as AU$520. 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 HARBOUR ALL-INCLUSIVE DINNER CRUISE

Sydney Harbour Dinner Cruise

AU$159
per adult
100% of travellers recommend
Sydney Harbour Dinner Cruise
Woman at the Sydney Opera House

Great Opera Hits at the Sydney Opera House

AU$69
per adult
100% of travellers recommend
Great Opera Hits at the Sydney Opera House
Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise

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

AU$88
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.