Winston Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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
Price found within the past 48 hours. Click for updated prices.
  • Front of property
    Aug 17 - Aug 21

    YEHS Hotel Sydney CBD + Flight

    Sydney Central Business District
    2 nights
    3.5 star property
    8.2/10 - Very good (1,001 reviews)
    "Centrally located. We love the location. Also the staff are helpful."
    Reviewed May 17, 2026
    Roundtrip • Calgary (YYC) - Sydney (SYD)
    YYC - SYD • 2 stops SYD - YYC • 2 stops
    CA $2,149
    CA $1,895
    per traveller
    found 1 day ago
    YEHS Hotel Sydney CBD
  • Front of property - evening/night
    Jul 11 - Jul 19

    Sofitel Sydney Darling Harbour + Flight

    Sydney Central Business District
    6 nights
    5.0 star property
    9.0/10 - Wonderful (1,005 reviews)
    "Excellent all round. Can't fault it."
    Reviewed May 16, 2026
    Roundtrip • Edmonton (YEG) - Sydney (SYD)
    YEG - SYD • 2 stops SYD - YEG • 2 stops
    CA $3,930
    CA $3,406
    per traveller
    found 1 day ago
    Sofitel Sydney Darling Harbour
  • Restaurant
    Jul 8 - Jul 14

    YEHS Hotel Sydney Harbour Suites + Flight

    Sydney Central Business District
    4 nights
    4.0 star property
    8.2/10 - Very good (2,741 reviews)
    "Very good staff and very clean room and a great experience all around"
    Reviewed May 23, 2026
    Roundtrip • Toronto (YYZ) - Sydney (SYD)
    YYZ - SYD • 2 stops SYD - YYZ • 2 stops
    CA $3,009
    CA $2,635
    per traveller
    found 1 day ago
    YEHS Hotel Sydney Harbour Suites
  • Terrace/patio
    Aug 9 - Aug 15

    The Old Clare by Ode Hotels + Flight

    Chippendale
    4 nights
    4.5 star property
    9.2/10 - Wonderful (570 reviews)
    "Beautiful and characterful room, very spacious, located in a great area."
    Reviewed May 15, 2026
    Roundtrip • Toronto (YYZ) - Sydney (SYD)
    YYZ - SYD • 2 stops SYD - YYZ • 2 stops
    CA $2,638
    CA $2,322
    per traveller
    found 11 hours ago
    The Old Clare by Ode Hotels
  • Exterior
    Jul 11 - Jul 19

    Furama Darling Harbour + Flight

    Haymarket
    6 nights
    4.0 star property
    8.4/10 - Very good (1,001 reviews)
    "Perfect t "
    Reviewed May 17, 2026
    Roundtrip • Edmonton (YEG) - Sydney (SYD)
    YEG - SYD • 2 stops SYD - YEG • 2 stops
    CA $3,624
    CA $3,202
    per traveller
    found 1 day ago
    Furama Darling Harbour

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(383 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 CA $304 per night from May 31 to Jun 1
CA $304
CA $335 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (2,176 reviews)
"Beds comfortable excellent staff & service. Had great view of Sydney Harboir from our room on 14th Floor"

Reviewed on May 23, 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 CA $300 per night from Jun 8 to Jun 9
CA $300
CA $330 total
Jun 8 - Jun 9
includes taxes & fees
9.2/10 Wonderful! (2,681 reviews)
"Great property to visit with young adult. Great location..."

Reviewed on May 22, 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 CA $268 per night from Jun 1 to Jun 2
CA $268
CA $294 total
Jun 1 - Jun 2
includes taxes & fees
9/10 Wonderful! (2,045 reviews)
"Great location. Views from zephyr bar were stunning"

Reviewed on May 22, 2026

Hyatt Regency Sydney
See all 5,981 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 . 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 Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

CA $51
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

CA $322
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

CA $32
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
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.