Winston Hills Vacations from ￥154,521

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The Latest Winston Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Airport Hotel Sydney

Airport Hotel Sydney

3.5 out of 5
Arncliffe
Price was ￥212,195, price is now ￥154,521 per person
￥154,521
per person
Jun 21 - Jun 26
found 20 hours ago
Roundtrip flight included
Tokyo (TYO) to Sydney (SYD)
6.2/10 (542 reviews)
Was a bit scary at 4.15 am when leavi ng through the side door to be meet by a drunk guy wanting to give me a hug. Luckily the taxi came a little early. Just got a fright when going out the door, as i didn't see him there.

Reviewed on Apr 10, 2026

Native Rose Hotel

Native Rose Hotel

2 out of 5
Rozelle
Price was ￥224,308, price is now ￥167,918 per person
￥167,918
per person
Aug 6 - Aug 13
found 6 hours ago
Roundtrip flight included
Tokyo (HND) to Sydney (SYD)
8/10 Very Good! (15 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 Aug 16, 2025

Mariners Court Hotel Sydney

Mariners Court Hotel Sydney

3.5 out of 5
Woolloomooloo
Price was ￥217,080, price is now ￥166,453 per person
￥166,453
per person
Jun 21 - Jun 26
found 20 hours ago
Roundtrip flight included
Tokyo (TYO) to Sydney (SYD)
8.6/10 Excellent! (1,002 reviews)
Great View of the harbor which was the point of our selection for staying.

Reviewed on May 12, 2026

The William Inglis Hotel - MGallery Hotel Collection

The William Inglis Hotel - MGallery Hotel Collection

5 out of 5
Warwick Farm
Price was ￥214,955, price is now ￥168,169 per person
￥168,169
per person
Jun 21 - Jun 26
found 16 hours ago
Roundtrip flight included
Tokyo (TYO) to Sydney (SYD)
9.2/10 Wonderful! (508 reviews)
Very Calm environment, simple and elegant interior, nothing flashy or shiny. At the time of Checkout, we met "Moss The Boss", oh, he was such an amazing person and the best asset of any Organization.

Reviewed on May 9, 2026

The Clarence Hotel Sydney by Accor

The Clarence Hotel Sydney by Accor

3.5 out of 5
Sydney Central Business District
Price was ￥266,654, price is now ￥209,512 per person
￥209,512
per person
Aug 6 - Aug 13
found 6 hours ago
Roundtrip flight included
Tokyo (HND) to Sydney (SYD)
9/10 Wonderful! (60 reviews)
Quaint boutique hotel. The room was small but was all I needed for two nights.

Reviewed on May 12, 2026

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

Sydney Central Business District

3 out of top 10 points of interest in this area
4.5/5(1,344 area reviews)

Historical and commercial heart of Sydney, the CBD boasts towering skyscrapers, lively café culture, and nightlife in areas like Darling Harbour. Explore parks such as Hyde Park and cultural institutions, while enjoying easy access to public transport.

Find hotels in Sydney Central Business District

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 ￥34,669 per night from Jun 16 to Jun 17
￥34,669
￥38,136 total
Jun 16 - Jun 17
includes taxes & fees
9.6/10 Exceptional! (2,173 reviews)
N/A

Reviewed on May 15, 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 ￥33,534 per night from May 17 to May 18
￥33,534
￥36,888 total
May 17 - May 18
includes taxes & fees
9.2/10 Wonderful! (2,666 reviews)
We requested some things on check in and it took 3 phone calls before they were delivered to our room. The rooms are a little tired. Room was not soundproof. Beautiful view, but the windows were dirty. We couldn't use the top floor bar as there was a private function booked.

Reviewed on May 14, 2026

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 ￥27,766 per night from Jun 14 to Jun 15
￥27,766
￥30,543 total
Jun 14 - Jun 15
includes taxes & fees
8.8/10 Excellent! (2,038 reviews)
Clean, great location, beautiful inside, great staff. Sumi at the bar was helpful and gave us hot water for tea. She was lovely and so were all the other staff members .

Reviewed on May 16, 2026

Hyatt Regency Sydney
See all 6,020 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.

Frequently asked questions

How much does a Winston Hills vacation package cost?
Discover the best of Winston Hills from as little as ￥154,521. 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 vacation 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 vacation!
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 vacation?
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 favorite 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, cozy city apartments and even houseboats and castles!
Can I choose my airline with a Winston Hills Expedia vacation package?
With a vacation 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 vacation 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 vacation 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

Sydney Opera House

Sydney Opera House

One of the world’s most famous buildings is surprisingly accessible; take in a show or just take a stroll to admire this astonishing building.

Sydney Opera House
Circular Quay

Circular Quay

Flanked by the Opera House and Harbour Bridge, Sydney’s transportation hub is one of the prettiest terminals in the world.

Circular Quay
Sydney Harbour Bridge

Sydney Harbour Bridge

Stroll from end-to-end or climb to the top; either way, Sydney’s “Coat Hanger” serves up memories to last a lifetime.

Sydney Harbour Bridge

Things to do

Sydney Hop-On Hop-Off Big Bus Tour

Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

￥7,218
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

￥5,809
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Woman at the Sydney Opera House

Great Opera Hits at the Sydney Opera House

￥7,694
per adult
100% of travellers recommend
Great Opera Hits at the Sydney Opera House
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.