Title: Winston Hills Vacation Packages | Holiday Packages & Trips 2026/2027 from CA $2,750 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. ![3-bed Apartment in Beautiful Kiama With Study Nook](https://images.trvl-media.com/lodging/123000000/122310000/122304800/122304764/1e293e78_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### 3-bed Apartment in Beautiful Kiama With Study Nook CA $2,750 per person Apr 26 - May 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) No reviews ![Pristine 3-bed Kiama Unit With Courtyard](https://images.trvl-media.com/lodging/123000000/122230000/122220300/122220260/ce94805b_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Pristine 3-bed Kiama Unit With Courtyard CA $2,945 per person Apr 26 - May 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) 8/10 Very Good! (1 review) ![Ground Floor Spacious Home in Kiama's Heart](https://images.trvl-media.com/lodging/123000000/122170000/122170000/122169908/a8cfb066_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Ground Floor Spacious Home in Kiama's Heart CA $2,828 per person Apr 26 - May 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) No reviews ![Lovely 3-bed With Alfresco Dining](https://images.trvl-media.com/lodging/123000000/122200000/122190900/122190885/1479aee3_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### Lovely 3-bed With Alfresco Dining CA $2,762 per person Apr 26 - May 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) No reviews ![First Floor 3-bed Stunning Unit by The Ocean](https://images.trvl-media.com/lodging/123000000/122200000/122198800/122198746/00575636_y.jpg?impolicy=fcrop&w=900&h=506&q=mediumHigh) ### First Floor 3-bed Stunning Unit by The Ocean CA $2,764 per person Apr 26 - May 1 found 1 day ago Roundtrip flight included Toronto (YTO) to Sydney (SYD) No reviews ## 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(382 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(61 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) ![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) ![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 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) ![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) ## Winston Hills Hotel Deals ![Shangri-La Sydney](https://images.trvl-media.com/lodging/1000000/20000/12000/11974/b0b86b8b_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 $265 CA $292 total Apr 19 - Apr 20 includes taxes & fees 9.2/10 Wonderful! (2,553 reviews) Stayed the night at the hotel and the staff was amazing and we every helpful. The view from the room was amazing and bed so comfortable. Watched a beautiful sunrise in the morning. Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=19%2F04%2F2026&endDate=20%2F04%2F2026&selected=11974&PinnedHotelID=11974&HadPinnedHotel=true®ionId=3000463469) ![Rydges Sydney Airport Hotel](https://images.trvl-media.com/lodging/6000000/5940000/5932400/5932305/dd75ee82_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Rydges Sydney Airport Hotel 8 Arrival Court Mascot NSW Fully refundableReserve now, pay when you stay CA $199 CA $219 total Mar 28 - Mar 29 includes taxes & fees 8.8/10 Excellent! (3,067 reviews) Very convenient for the Airport and despite being so close a very peaceful night sleep ( and that's coming from a light sleeper!). We had an airport facing window which was great to watch the flight land and depart. Prices at the bar are not cheep and no local shops so come prepared if this is an ... Reviewed on Mar 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=28%2F03%2F2026&endDate=29%2F03%2F2026&selected=5932305&PinnedHotelID=5932305&HadPinnedHotel=true®ionId=3000463469) ![Hyatt Regency Sydney](https://images.trvl-media.com/lodging/1000000/20000/15900/15886/c4f7df02_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Hyatt Regency Sydney 161 Sussex Street Sydney NSW Fully refundableReserve now, pay when you stay CA $236 CA $259 total Mar 31 - Apr 1 includes taxes & fees 8.8/10 Excellent! (1,952 reviews) Great Reviewed on Mar 23, 2026 [](https://expedia.ca/Hotel-Search?startDate=31%2F03%2F2026&endDate=01%2F04%2F2026&selected=15886&PinnedHotelID=15886&HadPinnedHotel=true®ionId=3000463469) [See all 5,978 properties in Winston Hills](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=25%2F03%2F2026&endDate=26%2F03%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 ![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(447 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) ![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(425 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 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(412 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 $67 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 $288 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.