Title:  Winston Hills Vacation Packages & Trips 2025 from $1,892 | Expedia.ca

  

[Hotels in Winston Hills](https://expedia.ca/Winston-Hills-Sydney-Hotels.0-n3000463469-0.Travel-Guide-Filter-Hotels)[Flights to Sydney](https://expedia.ca/Cheap-Flights-To-Sydney.d178312.Travel-Guide-Flights)[Things to do in Sydney](https://expedia.ca/Things-To-Do-In-Sydney.d178312.Travel-Guide-Activities)[Winston Hills Car Rentals](https://expedia.ca/Car-Rentals-In-Winston-Hills.d3000463469.Car-Rental-Guide)

![](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_packages.jpeg?impolicy=fcrop&w=1200&h=300&q=medium)

# 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 $1,096 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

## Top Holiday Package Deals in Winston Hills

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

![YEHS Hotel Sydney QVB](https://images.trvl-media.com/lodging/32000000/31200000/31199500/31199461/d35c9f07_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### YEHS Hotel Sydney QVB

Sydney Central Business District

CA $2,343

per person

Oct 24 - Oct 28

found 1 day ago

Roundtrip flight included

Edmonton (YEG) to Sydney (SYD)

8.6/10 Excellent! (1,005 reviews)

24 hour concierge, central location.

Reviewed on Sep 16, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-10-24/2025-10-28/?FromAirport=YEG&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=31199461&paandie=true&dealMarker=owaIBlbrObzc9OgD9Pr0Da6S3hDre8yxoBgWwAja-DlN92n5wlJvDcvZkuS6R1us)

![YEHS Hotel Sydney CBD](https://images.trvl-media.com/lodging/13000000/12460000/12456600/12456551/7f9c48b5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### YEHS Hotel Sydney CBD

Sydney Central Business District

CA $2,643

per person

Dec 9 - Dec 13

found 8 hours ago

Roundtrip flight included

Toronto (YYZ) to Sydney (SYD)

8.2/10 Very Good! (1,002 reviews)

Amazing location. Nice and clean. Super friendly staff

Reviewed on Sep 18, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-12-09/2025-12-13/?FromAirport=YYZ&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=12456551&paandie=true&dealMarker=45fiTByaY2pXBgsfwX7WcRw0eMlsZAgl2WZVgXT68EiszelcTfdu5T7nOJSPkSw_)

![Capella Sydney](https://images.trvl-media.com/lodging/90000000/89650000/89646400/89646350/75184b88_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Capella Sydney

Sydney Central Business District

CA $3,450

per person

Nov 24 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Sydney (SYD)

9.8/10 Exceptional! (316 reviews)

We liked the friendliness and the efficiency of the staff We missed the fruit offering in the room

Reviewed on Sep 15, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-29/?FromAirport=YVR&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=89646350&paandie=true&dealMarker=Ow-Q0z5ZIEEdBymoJ4wUiHsCjmKrR1AVSJ_vgoiRLia2zTOiLP7rEUfUa6L7_ehp)

![The Old Clare by Ode Hotels](https://images.trvl-media.com/lodging/12000000/11270000/11262400/11262386/a193e588_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The Old Clare by Ode Hotels

Chippendale

CA $2,445

per person

Nov 24 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Sydney (SYD)

9.2/10 Wonderful! (533 reviews)

Boutique hotel that's only 10 years old but already showing it's age. Some design elements quite dated and room basics like cupboards and carpets show wear and tear. Light switches and aircon control poorly located in the loft room that I booked. I was expecting luxury from the photos, but the reality felt like a 3~4 star hotel, not 5 star.

Reviewed on Sep 15, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-29/?FromAirport=YVR&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=11262386&paandie=true&dealMarker=Ow-Q0z5ZIEEdBymoJ4wUiFypdDfX0pL4iDEIwA_rE0hpl2YS-PP3bi86pJvOkJVw)

![SKYE Suites Sydney](https://images.trvl-media.com/lodging/25000000/24510000/24507600/24507540/0bd3a563_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### SKYE Suites Sydney

Sydney Central Business District

CA $2,715

per person

Nov 24 - Nov 29

found 1 day ago

Roundtrip non-stop flight included

Vancouver (YVR) to Sydney (SYD)

9.4/10 Exceptional! (766 reviews)

Such a nice quiet place and relaxing place to stay.

Reviewed on Sep 21, 2025

[](https://expedia.ca/go/package/search/FlightHotel/2025-11-24/2025-11-29/?FromAirport=YVR&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=24507540&paandie=true&dealMarker=Ow-Q0z5ZIEEdBymoJ4wUiOhhkJs_XPW31uL7-MtDkOa6AlJI_sR_QQOOrq49NpXx)

## 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](https://expedia.ca/Sydney-Winston-Hills.dx3000463469)

![Default Image](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/152000/152944-Sydney-Town-Hall.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sydney Central Business District

2 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 hotel + flight trips in Sydney Central Business District](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sydney%20Central%20Business%20District&DestID=6050650&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Darling Harbour showing city views, a bay or harbour and a city](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31111-Darling-Harbour.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Darling Harbour

4.5/5(60 area reviews)

Adjacent to Sydney's city centre, Darling Harbour boasts a pedestrian precinct with attractions like the Australian National Maritime Museum and Chinese Garden of Friendship. Enjoy dining at Cockle Bay Wharf, explore Tumbalong Park, and access various transport options, including the Inner West Light Rail and ferry services.

[Find hotel + flight trips in Darling Harbour](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Darling%20Harbour&DestID=6047418&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Default Image](https://mediaim.expedia.com/destination/1/f62173c58edbe39e125473be1dd47291.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Sydney Olympic Park

1 out of top 10 points of interest in this area

Featuring a large sports and entertainment area, commercial developments, and extensive parklands, this Greater Western Sydney suburb offers attractions like Bicentennial Park and Newington Armory. Easily accessible via Olympic Park railway line and ferry services.

[Find hotel + flight trips in Sydney Olympic Park](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Sydney%20Olympic%20Park&DestID=6134346&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Manly Beach featuring a coastal town, tropical scenes and a beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/31000/31187-Manly-Beach.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Manly

Beach-side suburb with easy ferry access, Manly offers a mix of ocean and harbor beaches, scenic cycle tracks, and a lively commercial area along The Corso. Explore historic sites like North Head Quarantine Station and enjoy outdoor dining.

[Find hotel + flight trips in Manly](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Manly&DestID=7055&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

![Bondi Beach featuring general coastal views, a coastal town and a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/251000/251855-Bondi.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Bondi Beach

A noteworthy feature of Bondi Beach is its stunning beaches. While you're in town, be sure to stop and check out Bondi Beach and Bondi Icebergs.

[Find hotel + flight trips in Bondi Beach](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Bondi%20Beach&DestID=6132031&DaysInFuture=30&StayLength=7&rfrr=TG.LP.Dest.PKG.Neighborhoods)

## Winston Hills Hotel Deals

![Four Seasons Hotel Sydney](https://images.trvl-media.com/lodging/1000000/10000/2300/2220/a7811611_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Four Seasons Hotel Sydney

199 George St., Sydney, NSW

Fully refundableReserve now, pay when you stay

CA $302

CA $332 total

Sep 25 - Sep 26

includes taxes & fees

9.6/10 Exceptional! (1,955 reviews)

"It was my 30th bday and we had just gotten engaged and they gave us a free bottle of champagne to celebrate! They helped with bags, they really were just so nice and friendly and the room was gorgeous!"

Reviewed on Sep 17, 2025

[](https://expedia.ca/Hotel-Search?startDate=25%2F09%2F2025&endDate=26%2F09%2F2025&selected=2220&PinnedHotelID=2220&HadPinnedHotel=true&regionId=3000463469)

![Shangri-La Sydney](https://images.trvl-media.com/lodging/1000000/20000/12000/11974/4d64faa5_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Shangri-La Sydney

176 Cumberland Street, The Rocks, NSW

Fully refundableReserve now, pay when you stay

CA $260

CA $286 total

Oct 12 - Oct 13

includes taxes & fees

9/10 Wonderful! (2,405 reviews)

"The view was amazing from the room"

Reviewed on Sep 18, 2025

[](https://expedia.ca/Hotel-Search?startDate=12%2F10%2F2025&endDate=13%2F10%2F2025&selected=11974&PinnedHotelID=11974&HadPinnedHotel=true&regionId=3000463469)

![Hyatt Regency Sydney](https://images.trvl-media.com/lodging/1000000/20000/15900/15886/d068b4c6_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Hyatt Regency Sydney

161 Sussex Street, Sydney, NSW

Fully refundableReserve now, pay when you stay

CA $245

CA $269 total

Oct 9 - Oct 10

includes taxes & fees

8.8/10 Excellent! (1,814 reviews)

"Beautiful property. Close to restaurants and bars."

Reviewed on Sep 15, 2025

[](https://expedia.ca/Hotel-Search?startDate=09%2F10%2F2025&endDate=10%2F10%2F2025&selected=15886&PinnedHotelID=15886&HadPinnedHotel=true&regionId=3000463469)

[See all 5,488 properties in Winston Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=22%2F09%2F2025&endDate=23%2F09%2F2025&regionId=3000463469)

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.

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

All Inclusive Vacations

[](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Beach Vacations

[](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Family Vacations

[](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Golf Vacations

[](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Luxury Vacations

[](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Romantic Vacations

[](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click)

![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh)

Ski Vacations

[](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click)

## Frequently asked questions

### How much does a Winston Hills vacation package cost?

> Discover the best of Winston Hills from as little as CA $2,343. 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](https://www.expedia.ca/service/?langid=4105). 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

![Circular Quay featuring general coastal views, a sunset and central business district](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/152000/152942-Circular-Quay.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Circular Quay

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

[](https://expedia.ca/Circular-Quay-The-Rocks.d502951.Vacation-Attraction)

![Sydney Opera House](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/474000/474916-Sydney-Opera-House.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

[](https://expedia.ca/Sydney-Opera-House-Sydney-Central-Business-District.d502962.Vacation-Attraction)

![Sydney Harbour Bridge](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/543000/543113-sydney-harbour-bridge.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### 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.

[](https://expedia.ca/Sydney-Harbour-Bridge-Sydney.d508804.Vacation-Attraction)

### Things to do

![Picture 11 for Activity Blue Mountains: Scenic World, Ferry, Zoo & Free Koala Photo](https://mediaim.expedia.com/localexpert/49246219/7bf33dc4-8468-4574-8b69-baecc50102f3.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Blue Mountains Adventure: Scenic World, Zoo & Koala Photo

CA $190

per adult

**90%** of travellers recommend

[](https://expedia.ca/things-to-do/blue-mountains-adventure-scenic-world.a49246219.activity-details)

![Sydney Opera House Tour & Meal + Drink at Opera Bar or House Canteen](https://mediaim.expedia.com/localexpert/3670715/3893300c-8a58-47a4-8e78-5195483bec23.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sydney Opera House Tour & Dine Experience

CA $80

per adult

**96%** of travellers recommend

[](https://expedia.ca/things-to-do/sydney-opera-house-tour-dine-experience.a3670715.activity-details)

![Sydney: Blue Mountains National Park Tour with River Cruise](https://mediaim.expedia.com/localexpert/48574923/029b8128-bf55-4db5-9d95-d6bb03aa70ee.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sydney: Blue Mountains National Park Tour with River Cruise

CA $81

per adult

**100%** of travellers recommend

[](https://expedia.ca/things-to-do/sydney-blue-mountains-national-park-tour-with-river-cruise.a48574923.activity-details)

[See all activities in Sydney](https://expedia.ca/things-to-do/search?rid=3000463469)

\* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.