Winston Hills Holidays from AU$449

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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.
Coogee Bay Hotel

Coogee Bay Hotel

3.5 out of 5
Coogee
Save 100% on your flight
Price was AU$706, price is now AU$449 per person
AU$449
per person
11 Nov - 14 Nov
found 24 hours ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
9.2/10 Wonderful! (111 reviews)
What an amazing night we had for our anniversary! Staff were amazing and the room was just to die for, thanks so much!!

Reviewed on 21 Sept 2025

Airport Hotel Sydney

Airport Hotel Sydney

3.5 out of 5
Arncliffe
Save 100% on your flight
Price was AU$1,703, price is now AU$972 per person
AU$972
per person
5 Nov - 12 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
6/10 (421 reviews)
I was worried with it being outside airport shuttle range .but local public bus transport was faster and cheaper. Room was small but very comfortable..will definitely stay here again. Loved the decor

Reviewed on 22 Sept 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$1,329, price is now AU$786 per person
AU$786
per person
6 Nov - 8 Nov
found 1 day ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.2/10 Very Good! (1,002 reviews)
Amazing location. Nice and clean. Super friendly staff

Reviewed on 18 Sept 2025

Native Rose Hotel

Native Rose Hotel

2 out of 5
Rozelle
Save 100% on your flight
Price was AU$991, price is now AU$600 per person
AU$600
per person
14 Nov - 18 Nov
found 24 hours ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
8/10 Very Good! (7 reviews)
Didn't dine at the property, but the food looks really good, bed was comfortable, t.v remote needs repairing and the window (room 5) everything easily accessible, Karaoke looks a hoot. Bathrooms are lovely

Reviewed on 16 Aug 2025

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$1,075, price is now AU$684 per person
AU$684
per person
14 Dec - 18 Dec
found 1 hour ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.6/10 Excellent! (1,005 reviews)
24 hour concierge, central location.

Reviewed on 16 Sept 2025

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
Default Image

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$385 per night from 28 Sept to 29 Sept
AU$385
28 Sept - 29 Sept
includes taxes & fees
9.6/10 Exceptional! (1,970 reviews)
"My all around experience was excellent. From hotel staff, food, to surrounding area I was happy for my choice. Will stay again ."

Reviewed on 24 Sept 2025

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$319 per night from 12 Oct to 13 Oct
AU$319
12 Oct - 13 Oct
includes taxes & fees
9/10 Wonderful! (2,397 reviews)
"Every aspect from the moment we checked in was faultless and the staff were so friendly and helpful. Probably the best hotel I’ve ever stayed in - and I’ve stayed in a few! Dr Jerry Evans MBE"

Reviewed on 25 Sept 2025

Shangri-La 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 AU$296 per night from 6 Oct to 7 Oct
AU$296
6 Oct - 7 Oct
includes taxes & fees
8.8/10 Excellent! (1,821 reviews)
"Great weekend stay right on the darling harbour"

Reviewed on 22 Sept 2025

Hyatt Regency Sydney
See all 5,430 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 holiday package cost?
Discover the best of Winston Hills from as little as AU$449. 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

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

Sydney Opera House

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

Sydney Harbour Bridge

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

Picture 11 for Activity Blue Mountains: Scenic World, Ferry, Zoo & Free Koala Photo

Blue Mountains Adventure: Scenic World, Zoo & Koala Photo

AU$208
per adult
90% of travellers recommend
Blue Mountains Adventure: Scenic World, Zoo & Koala Photo
Sydney Opera House Tour & Meal + Drink at Opera Bar or House Canteen

Sydney Opera House Tour & Dine Experience

AU$88
per adult
96% of travellers recommend
Sydney Opera House Tour & Dine Experience
Sydney: Blue Mountains National Park Tour with River Cruise

Sydney: Blue Mountains National Park Tour with River Cruise

AU$89
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River 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.