Winston Hills Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon

    Better together

    Save up to CA $1,096 when you book a flight and hotel together*
    lob hotels icon

    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon

    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.
Mariners Court Hotel Sydney

Mariners Court Hotel Sydney

3.5 out of 5
Woolloomooloo
Price was CA $2,778, price is now CA $2,348 per person
CA $2,348
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
8.4/10 Very Good! (1,024 reviews)
Quiet. close to shops, market and 20 minute coastal walk to opera house.

Reviewed on Aug. 31, 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Price was CA $3,201, price is now CA $2,381 per person
CA $2,381
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
8.2/10 Very Good! (1,001 reviews)
Despite being right in the middle of the city it was quiet and nice. Also for a small room it was still spacious and well equipped

Reviewed on Aug. 30, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was CA $3,419, price is now CA $2,754 per person
CA $2,754
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Sydney (SYD)
9/10 Wonderful! (584 reviews)
Quiet and convenient.

Reviewed on Aug. 23, 2025

Coogee Bay Boutique Hotel

Coogee Bay Boutique Hotel

4 out of 5
Coogee
Price was CA $3,205, price is now CA $2,640 per person
CA $2,640
per person
Nov 11 - Nov 16
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
8.8/10 Excellent! (827 reviews)
Great front desk staff, always helpful. Bowls full of Lindor chocolates in reception area …..yum.

Reviewed on Sep. 3, 2025

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was CA $3,094, price is now CA $2,605 per person
CA $2,605
per person
Nov 17 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Sydney (SYD)
8.2/10 Very Good! (2,250 reviews)
Nice staff and great cafe next door

Reviewed on Sep. 5, 2025

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
Default Image

Sydney Central Business District

2 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 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 $234 per night from Sep 14 to Sep 15
CA $234
CA $258 total
Sep 14 - Sep 15
includes taxes & fees
Shangri-La Sydney
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 $313 per night from Sep 7 to Sep 8
CA $313
CA $345 total
Sep 7 - Sep 8
includes taxes & fees
Four Seasons Hotel 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 $222 per night from Sep 14 to Sep 15
CA $222
CA $244 total
Sep 14 - Sep 15
includes taxes & fees
Hyatt Regency Sydney
See all 5,469 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 $2,348. 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

Circular Quay featuring general coastal views, a sunset and central business district

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 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
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

Picture 11 for Activity Blue Mountains: Scenic World, Ferry, Zoo & Free Koala Photo

Blue Mountains Adventure: Scenic World, Zoo & Koala Photo

CA $197
per adult
88% of travellers recommend
Blue Mountains Adventure: Scenic World, Zoo & Koala Photo
Sydney: Blue Mountains National Park Tour with River Cruise

Sydney: Blue Mountains National Park Tour with River Cruise

CA $89
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
Sydney Opera House Tour & Meal + Drink at Opera Bar or House Canteen

Sydney Opera House Tour & Dine Experience

CA $79
per adult
96% of travellers recommend
Sydney Opera House Tour & Dine Experience
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.