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 $4,200 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 QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
Price was CA $2,906, price is now CA $2,306 per person
CA $2,306
per person
Aug 8 - Aug 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
8.6/10 Excellent! (1,003 reviews)
Great value for money in the heart of Sydney. Very helpful staff.

Reviewed on Apr 28, 2026

Huge Harbour View Apartment In Historic Home

Huge Harbour View Apartment In Historic Home

2.5 out of 5
Cremorne
Price was CA $3,504, price is now CA $2,548 per person
CA $2,548
per person
Aug 8 - Aug 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
No reviews
Beachside Studio With Pool and Gym Access

Beachside Studio With Pool and Gym Access

2 out of 5
Cronulla
Price was CA $3,032, price is now CA $2,367 per person
CA $2,367
per person
Aug 8 - Aug 13
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
No reviews
Chic 1-bed Retreat Near Shops & Beach

Chic 1-bed Retreat Near Shops & Beach

2 out of 5
Manly
Price was CA $3,727, price is now CA $3,087 per person
CA $3,087
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
No reviews
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Price was CA $3,497, price is now CA $2,920 per person
CA $2,920
per person
Jul 18 - Jul 23
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
8.2/10 Very Good! (1,006 reviews)
Great location at CBD. Close to everything. As a female solo traveler, safety and convenience are my top priorities. This hotel works. My room was small and there is no view. My window faces another wall. But I don’t mind. The room was quiet and I got good rest after each day’s outing. No complaints.

Reviewed on Apr 30, 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

Sydney Central Business District

3 out of top 10 points of interest in this area
4.5/5(383 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 hotels in Sydney Central Business District

Winston Hills Hotel Deals

Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
The price is CA $299 per night from May 31 to Jun 1
CA $299
CA $329 total
May 31 - Jun 1
includes taxes & fees
9.6/10 Exceptional! (2,174 reviews)
The staff is great and very helpful. Highly recommended !

Reviewed on May 16, 2026

Four Seasons Hotel Sydney
Shangri-La Sydney

Shangri-La Sydney

5 out of 5
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
The price is CA $290 per night from May 17 to May 18
CA $290
CA $320 total
May 17 - May 18
includes taxes & fees
9.2/10 Wonderful! (2,669 reviews)
Excellent location. Reception staff very helpful but lacked local information which would have been of help i.e short cuts to the piers. Clean all over the hotel but house keeping lacking in our room, i.e not clean the first day. Furing stay, cutlery and linen napkin and glass wasn't taken away to ...

Reviewed on May 16, 2026

Shangri-La Sydney
Hyatt Regency Sydney

Hyatt Regency Sydney

5 out of 5
161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
The price is CA $265 per night from Jun 11 to Jun 12
CA $265
CA $291 total
Jun 11 - Jun 12
includes taxes & fees
8.8/10 Excellent! (2,039 reviews)
Clean, great location, beautiful inside, great staff. Sumi at the bar was helpful and gave us hot water for tea. She was lovely and so were all the other staff members .

Reviewed on May 16, 2026

Hyatt Regency Sydney
See all 6,030 properties in Winston Hills
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Winston Hills vacation package cost?
Discover the best of Winston Hills from as little as CA $2,306. 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.

Discover the most popular places to visit in Winston Hills

Sydney Opera House

Sydney Opera House

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.

Sydney Opera House
Circular Quay

Circular Quay

Flanked by the Opera House and Harbour Bridge, Sydney’s transportation hub is one of the prettiest terminals in the world.

Circular Quay
Sydney Harbour Bridge

Sydney Harbour Bridge

Stroll from end-to-end or climb to the top; either way, Sydney’s “Coat Hanger” serves up memories to last a lifetime.

Sydney Harbour Bridge

Things to do

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

CA $51
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

CA $322
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

CA $32
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
See all activities in Sydney
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.