Winston Hills Vacations from $1,656

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Your Winston Hills Vacation

Immerse yourself in all this neighborhood has to offer with a tailor-made Winston Hills vacation package. However you imagine spending your days here, you'll find countless opportunities for fun, adventure and relaxation. Start your trip to Winston Hills with a visit to nearby attractions such as Westfield Parramatta Shopping Centre, CommBank Stadium and Parramatta Park. No matter your travel goals or budget, booking your ideal Winston Hills vacation has never been easier with Expedia.

The Latest Winston Hills Vacation Packages

Price found within the past 48 hours. Click for updated prices.

Studio3: Chic Bondi Abode With Pool & A/C

Bondi Junction

$1,656

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

No reviews

YEHS Hotel Sydney Harbour Suites

Sydney Central Business District

$1,968

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8.2/10 Very Good! (2,874 reviews)

Pullman Sydney Hyde Park

Darlinghurst

$2,147

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8.6/10 Excellent! (1,005 reviews)

No outlets around beds

Reviewed on Aug 14, 2026

Adina Apartment Hotel Bondi Beach Sydney

Bondi Beach

$2,078

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

9.2/10 Wonderful! (1,178 reviews)

Both the girls at check in were first class and made my process so easy. A great place to stay in Bondi

Reviewed on Aug 10, 2026

Nesuto Woolloomooloo Sydney Apartments

Woolloomooloo

$1,733

per person

Nov 3 - Nov 8

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Sydney (SYD)

8.6/10 Excellent! (1,001 reviews)

We stayed in room 216 for three nights, it was great! Regina at front desk was awesome, letting us check in earlier after our long flight from the US. Apartments are spacious clean and comfortable, everything you need for a great stay! Close to all the sights if you are happy to walk, Circular Quay, Sydney Habour, Opera House, Botanical Gardens! Coffee place at the end of Dowling St was great! Bus stop close by to get to Bondi. Would stay again if coming back to Sydney!

Reviewed on Jul 29, 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

A historic clock tower with a modern skyscraper in the background.

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.

A nighttime cityscape with illuminated buildings reflecting on the water.

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.

A large, arched building with multiple entry points, including signs for 'Entry' and 'No entry'.

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.

A street with vintage buildings, pedestrians, and parked cars.

The Rocks

1 out of top 10 points of interest in this area

Historic area near Sydney's city center, The Rocks boasts close proximity to Circular Quay and Harbour Bridge views. Explore weekend Rocks Market, galleries, and historic pubs like Fortune of War, while enjoying walkable streets and easy rail access.

A crowded beach with people sunbathing and swimming, surrounded by buildings and trees.

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

Four Seasons Hotel Sydney

199 George St. Sydney NSW

$219 nightly

$241 total

Aug 23 - Aug 24

Total with taxes and fees

9.6/10 Exceptional! (2,247 reviews)

"Very good"

Reviewed on Aug 16, 2026

Shangri-La Sydney

176 Cumberland Street The Rocks NSW

Fully refundableReserve now, pay when you stay

$209 nightly

$230 total

Aug 23 - Aug 24

Total with taxes and fees

9.2/10 Wonderful! (2,816 reviews)

"We were disturbed twice when we had do not disturb notices on, minibar is very limited."

Reviewed on Aug 16, 2026

Hyatt Regency Sydney

161 Sussex Street Sydney NSW

Fully refundableReserve now, pay when you stay

$173 nightly

$191 total

Sep 13 - Sep 14

Total with taxes and fees

See all 6,251 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.