Winston Hills Holidays from £983

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Your Winston Hills Holiday

Experience everything this neighbourhood has to offer with a customized Winston Hills holiday package. However you picture yourself spending your time here, you'll find endless opportunities for relaxation, fun and adventure. When it's time to take in the sights, you'll find loads of big-name attractions nearby including CommBank Stadium, Westfield Parramatta Shopping Centre and Parramatta Park. Tick off one, two or all during your trip to Winston Hills. No matter what your ideal Winston Hills holiday looks like, you can make it a reality with Expedia.

Price found within the past 48 hours. Click for updated prices.
Beautiful Bondi 1-bed Apartment Meters From Beach

Beautiful Bondi 1-bed Apartment Meters From Beach

2 out of 5
Bondi Beach
Price was £1,214, price is now £983 per person
£983
per person
6 May - 10 May
found 1 day ago
Return direct flight included
London (LON) to Sydney (SYD)
No reviews
Haven Glebe

Haven Glebe

4.5 out of 5
Glebe
Price was £1,570, price is now £1,107 per person
£1,107
per person
10 Apr - 15 Apr
found 1 day ago
Return direct flight included
London (LHR) to Sydney (SYD)
8.8/10 Excellent! (981 reviews)
Room clean staff friendly close to shops

Reviewed on 23 Jan 2026

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Price was £1,163, price is now £1,003 per person
£1,003
per person
2 May - 5 May
found 1 day ago
Return direct flight included
London (LHR) to Sydney (SYD)
8.2/10 Very Good! (2,388 reviews)
Great staff, clean simple room, central location.

Reviewed on 11 Feb 2026

Spacious Inner-city House With Balcony Views

Spacious Inner-city House With Balcony Views

2.5 out of 5
Millers Point
Price was £2,348, price is now £1,684 per person
£1,684
per person
10 Apr - 13 Apr
found 1 day ago
Return direct flight included
London (LON) to Sydney (SYD)
No reviews
Central Bondi Studio With Rooftop Pool Access

Central Bondi Studio With Rooftop Pool Access

2 out of 5
Bondi
Price was £1,312, price is now £1,037 per person
£1,037
per person
6 May - 10 May
found 1 day ago
Return direct flight included
London (LON) 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
Sydney Town Hall featuring heritage architecture and a city

Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(343 area reviews)

Known for its captivating waterfront views and popular shops, there's plenty to explore in Sydney Central Business District. Check out top attractions like Circular Quay and Sydney Opera House, and jump on the metro at Martin Place Station or St. James Station to see more of the city.

Find hotels in Sydney Central Business District

Top hotels in Winston Hills

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 £181 per night from 8 Mar to 9 Mar
£181
8 Mar - 9 Mar
includes taxes & fees
9.6/10 Exceptional! (2,101 reviews)
Excellent view of opera house

Reviewed on 11 Feb 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 £172 per night from 8 Mar to 9 Mar
£172
8 Mar - 9 Mar
includes taxes & fees
9/10 Wonderful! (2,535 reviews)
Each member of the staff was very friendly and helpful. They took care of everything we needed plus. There was absolutely nothing I could find wrong. I strongly recommend upgrading to an upper floor. It included many extras you don’t get from a regular room. Worth the extra for upgrade.

Reviewed on 9 Feb 2026

Shangri-La Sydney
Ace Hotel Sydney

Ace Hotel Sydney

5 out of 5
47 Wentworth Ave Sydney NSW
Fully refundableReserve now, pay when you stay
The price is £259 per night from 22 Feb to 23 Feb
£259
22 Feb - 23 Feb
includes taxes & fees
9.2/10 Wonderful! (853 reviews)
Very nice

Reviewed on 12 Feb 2026

Ace Hotel Sydney
See all 6,060 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 Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Winston Hills travel package cost?
Our Winston Hills packages, which begin at just £983, are the easiest way to save loads of cash. Pick your preferred hotels, flights and rental car to create your dream itinerary.
If I'm not able to travel, can I cancel my Winston Hills travel package?
It's impossible to predict what tomorrow might bring, so it's comforting to know that you can change or cancel your Winston Hills travel package. If your booking was made in the last 24 hours, you may be entitled to a refund. If your booking is older, your hotel, airline or car rental company may charge a fee. Visit our Customer Service Portal for more information.
How do I get a cheap travel package to Winston Hills?
Creating your own Winston Hills travel package with Expedia is the easiest way to save. We have access to more than 550 air carriers and 1,000,000 hotels around the globe. With such an amazing range to pick from, you'll have no worries pulling together your dream holiday.
Does Expedia offer Book Now, Pay Later Winston Hills holidays?
Expedia has joined forces with online lender Klarna to make booking your next break easier on your budget. Paying by instalment means you can spread the costs of your dream holiday, leaving you with more money to spend while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that suits your budget. Consider these flexible payment options:

  • Pay monthly holidays: If paying bite-sized amounts each month sounds best for you, Klarna offers just that! Paying in easy monthly instalments will make your getaway dreams come true.
  • Pay in instalments holidays: Like the idea of paying off your holiday in multiple transactions? Then go for this Book Now, Pay Later option with Klarna.
  • Low deposit holidays: When you stumble on an unbeatable deal but your budget doesn't quite cover it yet, Klarna's low deposit holiday plan will help you secure your getaway.

Where should I stay in Winston Hills?
Take the hassle out of sightseeing by staying in a hotel just a stone's throw away from Winston Hills's big attractions. Sydney Opera House and Bondi Beach are two of the best in the area.
What are the top hotels in Winston Hills?
If this will be your first visit to Winston Hills, reserve a room at Sheraton Grand Sydney Hyde Park or Hyatt Regency Sydney. Both will make you feel at home and are popular options with many travellers.
How far in advance should I book my Winston Hills holiday?
To bag rock-bottom prices, book as early as you can. Air carriers usually release flight tickets, along with some of the lowest fares, around 12 months ahead of time. Hotels, experiences and car rental should also be booked early to avoid disappointment. If you were hoping for a last-minute getaway in Winston Hills, there are always lots of great bargains to be had on Expedia. Book something in today!
What does an Expedia Winston Hills travel package include?
Expedia has all you need to lock in Winston Hills trip, but how you structure your package is entirely up to you. Pick from any combination of flights, hotels and rental cars. In search of some tours or experiences to keep you on the go? Once you've made your booking, you can add them on too. Whatever your style, there's a travel package to meet your needs.
What should I know before booking a Winston Hills travel package?
You can look forward to saving with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with terrific discounts. You're not limited to hotels, though. Book with us and choose from island villas, city apartments and just about everything in between!
Can I choose my airline with a Winston Hills Expedia travel package?
Most definitely. Expedia has more than 550 partner airlines to pick from across the world. With so many choices, finding the ideal carrier to whisk you away to Winston Hills will be a breeze.

Popular places to visit

Circular Quay showing general coastal views, a skyscraper and street scenes

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 showing a bay or harbor, modern architecture and a monument

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 showing night scenes, a bridge and a sunset

Sydney Harbour Bridge

An iconic structure on a beautiful harbour with breath-taking views at any time of day or night. Climb it, walk it, photograph it or just stand back and admire it.

Sydney Harbour Bridge

Things to do

BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

£187
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
Woman at the Sydney Opera House

Great Opera Hits at the Sydney Opera House

£56
per adult
100% of travellers recommend
Great Opera Hits at the Sydney Opera House
Hansel & Gretel at Sydney Opera House

Hansel & Gretel at Sydney Opera House

£41
per traveller
Hansel & Gretel at Sydney Opera House
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. Flight-inclusive packages are ATOL protected.