Title: Winston Hills Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $2,465 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. ![The Ultimo](https://images.trvl-media.com/lodging/16000000/15700000/15696500/15696412/5704b338_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### The Ultimo Haymarket CA $2,465 per person Mar 15 - Mar 19 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) 8.8/10 Excellent! (1,000 reviews) Very well located pet friendly hotel that didn’t cost too much. We’ll definitely be back. Reviewed on Feb 7, 2026 ![InterContinental Sydney Double Bay by IHG](https://images.trvl-media.com/lodging/1000000/470000/460500/460480/06c06da7_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### InterContinental Sydney Double Bay by IHG Double Bay CA $3,330 per person Mar 26 - Mar 31 found 20 hours ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) 9/10 Wonderful! (596 reviews) Great staff very helpful Reviewed on Feb 6, 2026 ![APX Darling Harbour](https://images.trvl-media.com/lodging/1000000/920000/918500/918492/c2726e5d_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### APX Darling Harbour Sydney Central Business District CA $2,481 per person Mar 26 - Mar 31 found 20 hours ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) 7.6/10 Good! (1,001 reviews) Room was great, huge bed,location amazing but the men front of house, not that happy or helpful Reviewed on Jan 6, 2026 ![Ace Hotel Sydney](https://images.trvl-media.com/lodging/76000000/75080000/75072100/75072085/88c29d2c_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ace Hotel Sydney Sydney Central Business District CA $2,945 per person Mar 26 - Mar 31 found 20 hours ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) 9.4/10 Exceptional! (753 reviews) Fantastic hotel, loved it 5⭐️ Reviewed on Feb 10, 2026 ![West Hotel Sydney, Curio Collection by Hilton](https://images.trvl-media.com/lodging/21000000/20600000/20594100/20594078/ba17bbfb_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### West Hotel Sydney, Curio Collection by Hilton Sydney Central Business District CA $2,780 per person Mar 26 - Mar 31 found 20 hours ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) 9/10 Wonderful! (923 reviews) The rooms were clean but small. The hotel is nicely located. Its about 2 blocks from the train station. The staff was very accommodating Reviewed on Feb 2, 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 $305 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®ionId=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 $294 CA $323 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®ionId=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 CA $306 CA $336 total Mar 8 - Mar 9 includes taxes & fees 9.2/10 Wonderful! (850 reviews) Great place with artistic vibe. Rooms were eclectic. Bed and pillow excellent! Good lunch spot also. Stairs up into the lobby but someone there to help with the luggage. Reviewed on Feb 5, 2026 [](https://expedia.ca/Hotel-Search?startDate=08%2F03%2F2026&endDate=09%2F03%2F2026&selected=75072085&PinnedHotelID=75072085&HadPinnedHotel=true®ionId=3000463469) [See all 6,073 properties in Winston Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=11%2F02%2F2026&endDate=12%2F02%2F2026®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://images.trvl-media.com/place/502951/972c7825-5b25-4814-a0ac-6497e997c233.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 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 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 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 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 Hop-On Hop-Off Big Bus Tour](https://mediaim.expedia.com/localexpert/470655/1cf5f7fb-5c53-4eb7-a507-3afd0a863963.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) #### Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus CA $66 per adult **86%** of travellers recommend [](https://expedia.ca/things-to-do/big-bus-sydney-hop-on-hop-off-sightseeing-tour-by-open-top-bus.a470655.activity-details) ![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) [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.