Title: Winston Hills Vacation Packages | Holiday Packages & Trips 2026/2026 from CA $2,146 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 Harbour Suites](https://images.trvl-media.com/lodging/1000000/430000/426200/426104/144baa87_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### YEHS Hotel Sydney Harbour Suites Sydney Central Business District CA $2,146 per person Feb 5 - Feb 9 found 1 day ago Roundtrip flight included Calgary (YYC) to Sydney (SYD) 8.2/10 Very Good! (2,388 reviews) I stayed in a spacious room, great location. Proper CBD with everything within walking distance. Reviewed on Dec 10, 2025 ![APX World Square](https://images.trvl-media.com/lodging/3000000/2270000/2266500/2266432/f3e98fc1_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### APX World Square Haymarket CA $2,205 per person Feb 5 - Feb 9 found 1 day ago Roundtrip flight included Calgary (YYC) to Sydney (SYD) 8/10 Very Good! (2,719 reviews) Great stay, good clean & comfortable room, very quiet & with good bedding, friendly helpful staff. APX World Square is in a very good location, with easy to access to Chinatown light rail, Museum station 5 min walk & Central 10 min walk, very close to Capital Theatre & easy public transport to other Theatre's Including Royal, Lyric & Opera house. Every possible choice of food & drink requirements, Coles supermarket 3 min walk in the World Square centre. We will certainly be considering staying again for future visits Reviewed on Dec 9, 2025 ![Harbour Rocks by Ode Hotels](https://images.trvl-media.com/lodging/1000000/50000/41000/40904/f82639be_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Harbour Rocks by Ode Hotels The Rocks CA $2,392 per person Feb 5 - Feb 9 found 1 day ago Roundtrip flight included Calgary (YYC) to Sydney (SYD) 8.8/10 Excellent! (1,000 reviews) Very interesting hotel and location of the hotel. Close to shore walking, dining, sidewalk market (Fr -Su), ferry terminal. Pleasant and helpfull staff. No elevator, but staff helps with luggage up and down the stairs. We liked it very much. Reviewed on Nov 30, 2025 ![Spacious 3-bed Family House With Courtyard](https://images.trvl-media.com/lodging/123000000/122180000/122170800/122170775/a16e0865_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Spacious 3-bed Family House With Courtyard Balmain CA $2,328 per person Feb 16 - Feb 19 found 7 hours ago Roundtrip non-stop flight included Vancouver (YVR) to Sydney (SYD) No reviews ![The Porter House Hotel Sydney - MGallery](https://images.trvl-media.com/lodging/77000000/76810000/76802600/76802580/19b38fd2_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Porter House Hotel Sydney - MGallery Sydney Central Business District CA $2,360 per person Feb 5 - Feb 9 found 1 day ago Roundtrip flight included Calgary (YYC) to Sydney (SYD) 9.4/10 Exceptional! (253 reviews) Very well situated hotel in Sydney. The room was very clean, large and quiet. The staff at the hotel were super helpful and friendly. Highly recommend! Reviewed on Dec 13, 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](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) ![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) ![Parramatta showing a city and general coastal views](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/86000/86768-Parramatta.jpg?impolicy=fcrop&w=350&h=192&q=medium) ### Parramatta Major CBD and suburb, Parramatta boasts lush Parramatta Park, bustling Westfield shopping center, and diverse dining options on Church Street. Easily accessible via trains, buses, and ferries. [Find hotel + flight trips in Parramatta](https://expedia.ca/go/package/search/FlightHotel/?FromAirport=Downtown%20Columbus,%20Columbus,%20Ohio,%20United%20States%20of%20America&Destination=Parramatta&DestID=7274&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 $229 CA $252 total Jan 12 - Jan 13, 2026 includes taxes & fees 9/10 Wonderful! (2,436 reviews) lounges was lovely Reviewed on Dec 6, 2025 [](https://expedia.ca/Hotel-Search?startDate=12%2F01%2F2026&endDate=13%2F01%2F2026&selected=11974&PinnedHotelID=11974&HadPinnedHotel=true®ionId=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 $224 CA $246 total Dec 22 - Dec 23 includes taxes & fees 8.8/10 Excellent! (1,852 reviews) Very clean room with beautiful views Reviewed on Dec 12, 2025 [](https://expedia.ca/Hotel-Search?startDate=22%2F12%2F2025&endDate=23%2F12%2F2025&selected=15886&PinnedHotelID=15886&HadPinnedHotel=true®ionId=3000463469) ![View Sydney](https://images.trvl-media.com/lodging/1000000/480000/470900/470820/c63ef6c6_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### View Sydney 17 Blue Street North Sydney NSW Fully refundableReserve now, pay when you stay CA $180 CA $199 total Jan 11 - Jan 12, 2026 includes taxes & fees 9/10 Wonderful! (1,234 reviews) Great location. Very close to the train Reviewed on Dec 11, 2025 [](https://expedia.ca/Hotel-Search?startDate=11%2F01%2F2026&endDate=12%2F01%2F2026&selected=470820&PinnedHotelID=470820&HadPinnedHotel=true®ionId=3000463469) [See all 5,832 properties in Winston Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=14%2F12%2F2025&endDate=15%2F12%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? ### 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://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.