Title: Winston Hills Vacation Packages & Trips 2025 from CA $2,345 | 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. ![Serene Studio With Balcony in Prime Location](https://images.trvl-media.com/lodging/123000000/122210000/122204400/122204348/a1db0574_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Serene Studio With Balcony in Prime Location Wollstonecraft CA $1,976 per person Feb 5 - Feb 10 found 20 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Sydney (SYD) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2026-02-05/2026-02-10/?FromAirport=YVR&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=122204348&paandie=true&dealMarker=YuzTOQtUvagNoHumTfJT2GRmWBK30dqYlCtj0NG_YLU6kKmJY7ClP6MTER8wtF6x) ![Stylish 3-bed Newport Stay With Balcony](https://images.trvl-media.com/lodging/123000000/122230000/122220700/122220677/0f565058_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stylish 3-bed Newport Stay With Balcony Newport CA $5,938 per person Dec 31 - Jan 3 found 1 day ago Roundtrip non-stop flight included Toronto (YTO) to Sydney (SYD) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-12-31/2026-01-03/?FromAirport=YTO&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=122220677&paandie=true&dealMarker=XinlGwxp0EHvKcditEtyh4p37l-vpSQ3yMdHUJTwob3OlCYd1oF2BbulyrEy7t8V) ![King Size Studio With Water View, Walk To The City](https://images.trvl-media.com/lodging/123000000/122230000/122229000/122228930/049f38d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### King Size Studio With Water View, Walk To The City Woolloomooloo CA $2,524 per person Dec 26 - Dec 29 found 1 day ago Roundtrip flight included Calgary (YYC) to Sydney (SYD) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2025-12-26/2025-12-29/?FromAirport=YYC&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=122228930&paandie=true&dealMarker=cD5XS1Y6GX17UityUmD-znZo2htBkGi4y7OHSvjD59f3v9elcMWBiMAyRDy6qvIG) ![Stylish Studio in the Heart of Vibrant Surry Hills](https://images.trvl-media.com/lodging/123000000/122190000/122184800/122184791/0f0723d5_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Stylish Studio in the Heart of Vibrant Surry Hills Surry Hills CA $2,504 per person Jan 15 - Jan 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) No reviews [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-20/?FromAirport=YTO&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=122184791&paandie=true&dealMarker=Paq4skrmtZQlocDge_1LBIS8Nr9g7n-qccFszKsg4hEBWFQxxmCkYxQXtwEIs1EJ) ![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 $2,239 per person Jan 15 - Jan 20 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) 17.2/10 Exceptional! (1,002 reviews) Good location at a reasonable price. Good sized room and bathroom. Reviewed on Nov 22, 2025 [](https://expedia.ca/go/package/search/FlightHotel/2026-01-15/2026-01-20/?FromAirport=YTO&Destination=SYD&NumRoom=1&NumAdult=2&NumChild=0&hotelId=31199461&paandie=true&dealMarker=Paq4skrmtZQlocDge_1LBDIiEZAzqPOm4Pefpzm_VJGa0vxnWR5Zj7n2pWuBKHRD) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Limited-time deals: save up to 50% on select hotels [Book now](https://expedia.ca/deals?rfrr=PKG_BF_PROMO_3000463469) ## 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 1 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) ![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 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) ![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) ## Winston Hills Hotel Deals ![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 $253 CA $279 total Dec 15 - Dec 16 includes taxes & fees 9/10 Wonderful! (2,436 reviews) Staff were excellent very helpful and courteous. Reviewed on Nov 21, 2025 [](https://expedia.ca/Hotel-Search?startDate=15%2F12%2F2025&endDate=16%2F12%2F2025&selected=11974&PinnedHotelID=11974&HadPinnedHotel=true®ionId=3000463469) ![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 $309 CA $340 total Dec 16 - Dec 17 includes taxes & fees 9.6/10 Exceptional! (2,020 reviews) Service. Luxury. Reviewed on Nov 21, 2025 [](https://expedia.ca/Hotel-Search?startDate=16%2F12%2F2025&endDate=17%2F12%2F2025&selected=2220&PinnedHotelID=2220&HadPinnedHotel=true®ionId=3000463469) ![YEHS Hotel Sydney Harbour Suites](https://images.trvl-media.com/lodging/1000000/430000/426200/426104/144baa87_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### YEHS Hotel Sydney Harbour Suites 252 Sussex Street Sydney NSW CA $134 CA $147 total Dec 14 - Dec 15 includes taxes & fees 8.2/10 Very Good! (2,395 reviews) The location is great and the hotel staff is welcoming. It’s more run down than advertising videos show. Housekeeping was short staffed one day but we were ok with that and just asked for a couple of towels and received it right away. Honny and Sim at the front desk were extra helpful and wonderful ... Reviewed on Nov 18, 2025 [](https://expedia.ca/Hotel-Search?startDate=14%2F12%2F2025&endDate=15%2F12%2F2025&selected=426104&PinnedHotelID=426104&HadPinnedHotel=true®ionId=3000463469) [See all 5,759 properties in Winston Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=24%2F11%2F2025&endDate=25%2F11%2F2025®ionId=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 $1,976. 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 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. [](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 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. [](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 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. [](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 $49 per adult **84%** of travellers recommend [](https://expedia.ca/things-to-do/sydney-attractions-pass-including-sea-life-sydney-aquarium.a171990.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 $77 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) ![Sydney Tower Eye Tickets](https://mediaim.expedia.com/localexpert/462113/93d9eb03-f0c6-46d7-8d84-65ba72db353a.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Sydney Tower Eye Tickets CA $27 per adult **82%** of travellers recommend [](https://expedia.ca/things-to-do/sydney-tower-eye-tickets.a462113.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.