Winston Hills Vacation Packages

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    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
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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

3.5 out of 5
Sydney Central Business District
per person
Aug 24 - Aug 26
found 1 hour ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
8.2/10 Very Good! (1,000 reviews)
A charming little hotel smack bang in the middle of Sydney. Short walk to town hall station and darling Harbour. We, husband and the wee one stayed in a 1 bedroom apartment room and had an excellent time

Reviewed on Jun. 23, 2025

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
8.6/10 Excellent! (1,002 reviews)
Nothing standout but a good, average hotel. I didn’t like that my room didn’t have a window to the outside, but I also get that it’s right in the heart of the CBD and that isn’t always possible. The staff were wonderful though, so kind, friendly, and helpful!

Reviewed on Jul. 9, 2025

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
8.2/10 Very Good! (2,118 reviews)
Great place and convenient next to places to eat!

Reviewed on Jul. 8, 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
9.4/10 Exceptional! (1,003 reviews)
Excellent hotel and location!

Reviewed on Jul. 5, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
per person
Sep 30 - Oct 5
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
9/10 Wonderful! (570 reviews)
wonderful get away, five star experience. Breakfast is a must!

Reviewed on Jun. 24, 2025

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

3 out of top 10 points of interest in this area
4.5/5(381 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

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 CA $218 per night from Jul 18 to Jul 19
CA $218
CA $240 total
Jul 18 - Jul 19
includes taxes & fees
8.8/10 Excellent! (1,752 reviews)
"Excellent aspect, professional service and friendly staff, generous options for breakfast"

Reviewed on Jul. 6, 2025

Hyatt Regency 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 CA $215 per night from Jul 13 to Jul 14
CA $215
CA $237 total
Jul 13 - Jul 14
includes taxes & fees
8.8/10 Excellent! (2,301 reviews)
"Great Service, Friendly staff. Efficient check in and check out."

Reviewed on Jul. 7, 2025

Shangri-La Sydney
Rydges Sydney Airport Hotel
Rydges Sydney Airport Hotel
4 out of 5
8 Arrival Court, Sydney International Airport, Mascot, NSW
Fully refundableReserve now, pay when you stay
The price is CA $170 per night from Jul 14 to Jul 15
CA $170
CA $187 total
Jul 14 - Jul 15
includes taxes & fees
8.6/10 Excellent! (2,827 reviews)
"Big attraction is that it is close to International Terminal. So easy. Room was a tiny bit small but still fine. We loved the Ascot Restaurant! Every course was a standout. We had all seafood and super fresh."

Reviewed on Jul. 8, 2025

Rydges Sydney Airport Hotel
See all 5,484 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 Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Winston Hills vacation package cost?
Discover the best of Winston Hills from as little as CA $1,954. 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

4.5/5(446 reviews)

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 featuring general coastal views, a sunset and central business district

Circular Quay

4.5/5(424 reviews)

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

4.5/5(411 reviews)

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

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

Blue Mountains: Scenic World, Ferry, Zoo & Koala Photo

CA $176
per adult
92% of travellers recommend
Blue Mountains: Scenic World, Ferry, Zoo & Koala Photo
Sydney: Blue Mountains National Park Tour with River Cruise

Sydney: Blue Mountains National Park Tour with River Cruise

CA $88
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise

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

CA $76
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.