Winston Hills Vacation Packages
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to CA $4,200 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Medusa Boutique Hotel
Darlinghurst
CA $3,164
per person
Dec 8 - Dec 13
found 24 hours ago
Roundtrip flight included
Toronto (YYZ) to Sydney (SYD)
9.6/10 Exceptional! (498 reviews)
The rooms were gorgeous and the staff were super friendly and helpful. I would come back again for another staycation.
Reviewed on Oct 24, 2026
Elegant 1-bed by Riverside Park & Amenities
Canterbury
CA $4,900
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
6/10 (1 review)
Never got a response from the owner prior to arrival when I emailed with questions. Check in/out emails were all automated.
Apartment absolutely stunk of cigarette on arrival and despite using air freshener and keeping windows open alot, we never got the smell out.
Reviewed on Jun 8, 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
Sydney Central Business District
2 out of top 10 points of interest in this area
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.
Darling Harbour
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.
Sydney Olympic Park
2 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.
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 Pavilion.
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.
Winston Hills Hotel Deals
Shangri-La Sydney
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
CA $354
CA $389 total
Oct 26 - Oct 27
includes taxes & fees
Four Seasons Hotel Sydney
199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
CA $395
CA $434 total
Nov 8 - Nov 9
includes taxes & fees
Hyatt Regency Sydney
161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
CA $281
CA $309 total
Nov 2 - Nov 3
includes taxes & fees
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.
Frequently asked questions
How much does a Winston Hills vacation package cost?
Discover the best of Winston Hills from as little as CA $3,164. 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. 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.
Things to do
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
CA $51
per adult
86% of travellers recommend
Sydney Opera House Official Guided Walking Tour
CA $49
per adult
96% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
CA $320
per adult
98% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.