Title: Winston Hills Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $2,274 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

- ##  
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- ###  
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.

![THE PARK OASIS BURWOOD](https://images.trvl-media.com/lodging/118000000/117390000/117385000/117384997/43548bc3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### THE PARK OASIS BURWOOD

Burwood

CA $2,274

per person

Mar 26 - Mar 28

found 23 hours ago

Roundtrip flight included

Toronto (YYZ) to Sydney (SYD)

10/10 Exceptional! (5 reviews)

The room had great facilities and quiet!

Reviewed on Jan 15, 2026

![Ultimate Apartments Bondi Beach](https://images.trvl-media.com/lodging/2000000/1430000/1426900/1426897/499afba4_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Ultimate Apartments Bondi Beach

Bondi Beach

CA $2,374

per person

Mar 26 - Mar 28

found 23 hours ago

Roundtrip flight included

Toronto (YYZ) to Sydney (SYD)

8/10 Very Good! (1,105 reviews)

Cleaners need to be more thorough. I couldn't reach the air conditioner switch, and I'm not able to safely stand on a chair. It's a VERY old unit.

Reviewed on Dec 12, 2025

![Establishment Hotel](https://images.trvl-media.com/lodging/1000000/570000/564400/564346/2c2b5ae9_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Establishment Hotel

Sydney Central Business District

CA $2,610

per person

Mar 18 - Mar 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Sydney (SYD)

9/10 Wonderful! (658 reviews)

Extremely convenient, great bars down stairs. Great service.

Reviewed on Jan 18, 2026

![The William Inglis Hotel - MGallery Hotel Collection](https://images.trvl-media.com/lodging/21000000/20170000/20166000/20165912/w4695h3127x0y0-8ddc9f27_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### The William Inglis Hotel - MGallery Hotel Collection

Warwick Farm

CA $2,350

per person

Mar 18 - Mar 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Sydney (SYD)

9.2/10 Wonderful! (478 reviews)

Check in was easy. Amenities good. Nice and quiet, good views, the bed was comfy. No complaints.

Reviewed on Jan 6, 2026

![Quest Woolooware Bay](https://images.trvl-media.com/lodging/93000000/92510000/92507600/92507600/119107f7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

### Quest Woolooware Bay

Woolooware

CA $2,350

per person

Mar 18 - Mar 21

found 1 day ago

Roundtrip flight included

Toronto (YTO) to Sydney (SYD)

9.6/10 Exceptional! (131 reviews)

The accomodation was fantastic. Very clean and well appointed room. The only downside was the location. Unfortunately, the Woolooware Bay centre is a bit quiet. Lots of closed restaurants and shops. That said, if you have a car and don’t mind driving to restaurants, I would highly recommend.

Reviewed on Jan 25, 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](https://expedia.ca/Sydney-Winston-Hills.dx3000463469)

![Sydney Town Hall featuring heritage architecture and a city](https://images.trvl-media.com/place/502950/3976c6f9-4173-4359-8a39-120bd8a7447d.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### 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 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://images.trvl-media.com/place/6047418/a2d5eb62-42ce-4fd4-aa40-0b3492929009.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)

![Manly Beach featuring a coastal town, tropical scenes and a beach](https://images.trvl-media.com/place/6141018/85e1eaa5-5d3a-4635-a487-40ae8779972e.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://images.trvl-media.com/place/6060961/d440b634-7bec-47e1-8477-6ea1033b19e3.jpg?impolicy=fcrop&w=350&h=192&q=medium)

### Bondi Beach

1 out of top 10 points of interest in this area

 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 Markets. 

[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)

![500px Photo ID: 141620587 - The train station at Sydney Olympic Park was designed in a modern style for the Sydney 2000 Olympics.](https://images.trvl-media.com/place/6134346/13b8f86f-9124-4f54-b8b0-5e21754cd8f8.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)

## 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 $304

CA $335 total

Mar 8 - Mar 9

includes taxes & fees

9.6/10 Exceptional! (2,098 reviews)

Clean room! Slippers were placed on either side of the king bed. Room was all ready and waiting for us. It was very noisy on the street side at night which isn’t something they can really change. The only improvement the room needs is actual drawers! All of the ones under the TV are filled with coffee ...

Reviewed on Feb 5, 2026

[](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&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 $295

CA $324 total

Mar 9 - Mar 10

includes taxes & fees

9/10 Wonderful! (2,514 reviews)

everything was very good

Reviewed on Feb 4, 2026

[](https://expedia.ca/Hotel-Search?startDate=09%2F03%2F2026&endDate=10%2F03%2F2026&selected=11974&PinnedHotelID=11974&HadPinnedHotel=true&regionId=3000463469)

![Ace Hotel Sydney](https://images.trvl-media.com/lodging/76000000/75080000/75072100/75072085/88c29d2c_y.jpg?impolicy=resizecrop&rw=340&ch=150)

### 

Ace Hotel Sydney

47 Wentworth Ave Sydney NSW

Fully refundableReserve now, pay when you stay

CA $548

CA $602 total

Feb 19 - Feb 20

includes taxes & fees

9.2/10 Wonderful! (846 reviews)

Room was not spotless staff at front desk good

Reviewed on Feb 3, 2026

[](https://expedia.ca/Hotel-Search?startDate=19%2F02%2F2026&endDate=20%2F02%2F2026&selected=75072085&PinnedHotelID=75072085&HadPinnedHotel=true&regionId=3000463469)

[See all 6,073 properties in Winston Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=09%2F02%2F2026&endDate=10%2F02%2F2026&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?

### How do I get a cheap travel package to Winston Hills?

### Where should I stay in Winston Hills?

### How far in advance should I book my Winston Hills vacation?

### What does an Expedia Winston Hills travel package include?

### What should I know before booking a Winston Hills travel package?

### Can I choose my airline with a Winston Hills Expedia vacation package?

### If I'm not able to travel, can I cancel my Winston Hills vacation package?

### Discover the most popular places to visit in Winston Hills

![Circular Quay featuring general coastal views, a sunset and central business district](https://images.trvl-media.com/place/502951/972c7825-5b25-4814-a0ac-6497e997c233.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 showing a bay or harbor, modern architecture and a monument](https://images.trvl-media.com/place/502962/459302cf-7b27-4cb8-9e39-fbe072c060d9.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 showing night scenes, a bridge and a sunset](https://images.trvl-media.com/place/508804/7fecd070-d63b-4e64-8f81-83ae63ed464a.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

![Sydney Attractions Pass including SEA LIFE Sydney Aquarium](https://mediaim.expedia.com/localexpert/171990/c0a246ff-a176-425b-9229-96bb9df31164.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### Sydney Attractions Pass including SEA LIFE Sydney Aquarium

CA $47

per adult

**86%** of travellers recommend

[](https://expedia.ca/things-to-do/sydney-attractions-pass-including-sea-life-sydney-aquarium.a171990.activity-details)

![BridgeClimb Summit at Sydney Harbour Bridge](https://mediaim.expedia.com/localexpert/188962/57f1a1a0-bfbc-43b3-8014-858ea0617e7d.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

#### BridgeClimb Summit at Sydney Harbour Bridge

CA $349

per adult

**98%** of travellers recommend

[](https://expedia.ca/things-to-do/bridgeclimb-summit-at-sydney-harbour-bridge.a188962.activity-details)

![Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise](https://mediaim.expedia.com/localexpert/188986/4e814d56-d1d8-40f8-a06e-e9f969358e1a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh)

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

CA $81

per adult

**88%** of travellers recommend

[](https://expedia.ca/things-to-do/taronga-zoo-ticket-with-hop-on-hop-off-sydney-harbour-explorer-cruise.a188986.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.