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.
Mantra on Sydney Airport

Mantra on Sydney Airport

4 out of 5
Mascot
Price was CA $3,292, price is now CA $2,178 per person
CA $2,178
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
8.6/10 Excellent! (1,005 reviews)
The staff were particularly helpful

Reviewed on Jun 19, 2026

Stylish 2-bed House With Private Courtyard

Stylish 2-bed House With Private Courtyard

2.5 out of 5
Redfern
Price was CA $3,988, price is now CA $2,433 per person
CA $2,433
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
10/10 Exceptional! (1 review)
Excellent place for us to use as a base for vivisting Sydney for a short holiday. 5-10min walk from Redfern railway station meaning it was easy to move around the city.

Reviewed on May 5, 2026

The Old Clare by Ode Hotels

The Old Clare by Ode Hotels

4.5 out of 5
Chippendale
Price was CA $3,689, price is now CA $2,382 per person
CA $2,382
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
9.2/10 Wonderful! (574 reviews)
Lovely lovely property - beautiful location, amazing property beautifully restored, appropriate amenities and super super conveniently located. And the staff were really kind. And the rooftop bar is special!

Reviewed on Jun 8, 2026

Rydges Sydney Airport Hotel

Rydges Sydney Airport Hotel

4 out of 5
Mascot
Price was CA $3,559, price is now CA $2,341 per person
CA $2,341
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
8.8/10 Excellent! (3,222 reviews)
We only came to overnight before catching a flight in the morning. The location is terrific for that and well worth not dealing with Sydney traffic in a morning.

Reviewed on Jun 21, 2026

Rydges Camperdown

Rydges Camperdown

4 out of 5
Camperdown
Price was CA $3,414, price is now CA $2,254 per person
CA $2,254
per person
Jul 24 - Jul 29
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Sydney (SYD)
8.2/10 Very good! (1,004 reviews)
Clean simple large room. Had everything that was need for a short stay, and staff were very helpful. So close to central areas of Newtown.

Reviewed on Apr 12, 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

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 $271 per night from Jun 25 to Jun 26
CA $271
CA $298 total
Jun 25 - Jun 26
includes taxes & fees
9.2/10 Wonderful! (2,739 reviews)
"Great location, Great stay"

Reviewed on Jun 22, 2026

Shangri-La Sydney
Rydges Sydney Airport Hotel

Rydges Sydney Airport Hotel

4 out of 5
8 Arrival Court Mascot NSW
Fully refundableReserve now, pay when you stay
The price is CA $159 per night from Jun 25 to Jun 26
CA $159
CA $175 total
Jun 25 - Jun 26
includes taxes & fees
8.8/10 Excellent! (3,181 reviews)
"We only came to overnight before catching a flight in the morning. The location is terrific for that and well worth not dealing with Sydney traffic in a morning."

Reviewed on Jun 21, 2026

Rydges Sydney Airport Hotel
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 $343 per night from Jun 28 to Jun 29
CA $343
CA $377 total
Jun 28 - Jun 29
includes taxes & fees
9.6/10 Exceptional! (2,208 reviews)
"I finally made an official complaint to Four Seasons about the problem they have caused in returning my security deposite. This is the second times that happens, and I will suggest everyone who choose to stay in Four Seasons to double check how Four Seasons return your secuirty deposite."

Reviewed on Jun 22, 2026

Four Seasons Hotel Sydney
See all 6,110 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 $2,178. 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
Hunter Valley Full Day Tour

Hunter Valley: Wine Tour with 2-Course Lunch, Choc & Cheese

CA $218
per adult
Hunter Valley: Wine Tour with 2-Course Lunch, Choc & Cheese
BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

CA $372
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
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.