Chester Hill Holidays

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

Rydges Australia Square

4 out of 5
Sydney Central Business District
Price was S$1,931, price is now S$1,535 per person
S$1,535
per person
14 Feb - 18 Feb
found 5 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9.2/10 Wonderful! (1,714 reviews)
There was no breakfast served, but place is clean and comfortable except for the pilllows. Great location, close to Sydney Opera House, trains, etc.

Reviewed on 6 Jan, 2026

3-bedroom Home in the Heart of Darlinghurst

3-bedroom Home in the Heart of Darlinghurst

2.5 out of 5
Darlinghurst
Save 100% on your flight
Price was S$3,225, price is now S$2,331 per person
S$2,331
per person
14 Feb - 18 Feb
found 5 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
No reviews
InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was S$2,111, price is now S$1,552 per person
S$1,552
per person
14 Feb - 18 Feb
found 5 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9/10 Wonderful! (596 reviews)
Initial room was sub standard with mol

Reviewed on 13 Dec, 2025

Pullman Quay Grand Sydney Harbour

Pullman Quay Grand Sydney Harbour

5 out of 5
Sydney Central Business District
Price was S$2,557, price is now S$1,881 per person
S$1,881
per person
14 Feb - 18 Feb
found 5 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9.2/10 Wonderful! (1,002 reviews)
Great location and harbor view.Breakfast was excellent. Checking and checkout was easy and fast. Will stay again definitely.

Reviewed on 21 Dec, 2025

The Sebel Quay West Suites Sydney

The Sebel Quay West Suites Sydney

5 out of 5
The Rocks
Price was S$2,187, price is now S$1,660 per person
S$1,660
per person
14 Feb - 18 Feb
found 5 hours ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9.2/10 Wonderful! (2,374 reviews)
Great hotel. A little hard to find the entry but a clean, beautiful hotel with great facilities. The pool was sensational. Gym a little small. Great location though. Definitely be back.

Reviewed on 30 Dec, 2025

Where to stay in Chester Hill

Find the best Chester Hill areas and neighborhoods for the activities you enjoy most. Learn more about Chester Hill
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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 Chester Hill

Shangri-La Sydney

Shangri-La Sydney

5 out of 5
176 Cumberland Street The Rocks NSW
The price is S$269 per night from 14 Jan to 15 Jan
S$269
14 Jan - 15 Jan
includes taxes & fees
9/10 Wonderful! (2,455 reviews)
Room view over Sydney harbour over opera house

Reviewed on 30 Dec, 2025

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 S$345 per night from 11 Jan to 12 Jan
S$345
11 Jan - 12 Jan
includes taxes & fees
9.6/10 Exceptional! (2,067 reviews)
Clean room and very comfortable bed. Great views and location.

Reviewed on 5 Jan, 2026

Four Seasons Hotel Sydney
YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
252 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
The price is S$138 per night from 11 Jan to 12 Jan
S$138
11 Jan - 12 Jan
includes taxes & fees
8.2/10 Very Good! (2,474 reviews)
Lovely room nice staff and the right price

Reviewed on 2 Jan, 2026

YEHS Hotel Sydney Harbour Suites
See all 6,035 properties in Chester Hill
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.

Frequently asked questions

How much does a Chester Hill holiday package cost?
Be ready to book, because a trip to Chester Hill starts from an enticing S$1,535. When you combine your flights, hotels and car rentals into a package, you'll land the biggest bargains.
How do I get a cheap travel package to Chester Hill?
Combining your flight and hotel with Expedia won't just save you time — it'll save you money too. A Chester Hill holiday package makes it simple to arrange your perfect trip. With more than 550 airlines across the world to select from, finding convenient flights that fit your schedule will be no sweat. Not only that, we have over 1,000,000 hotel options globally to take your pick of. Now that's what you call choice. No matter who you are, Expedia puts the world within your reach.
Where should I stay in Chester Hill?
Most who travel to Chester Hill put both Sydney Opera House and Sydney Harbour Bridge on their sightseeing itineraries. Why not select a hotel close to one of these great attractions?
What are the top hotels in Chester Hill?
When it comes to comfy and convenient places to stay in Chester Hill, you can't beat Nightcap at Chester Hill Hotel. Browse its deals and pick up a bargain.
How far in advance should I book my Chester Hill holiday?
Search Expedia to compare international flights ASAP. You can generally purchase a seat up to a year before departure. If it's too early for your preferred carrier, or you've left things to the last moment, don't worry. Cheap fares to Chester Hill sometimes appear just weeks before departure.
What does an Expedia Chester Hill travel package include?
Rental cars, flights and hotels — we have them well covered. With Expedia, you can shape your Chester Hill travel package the way you want. All you have to do is work out what you need. Once you've made your booking, you can add extras like tours and activities. The more you bundle, the bigger the savings!
What should I know before booking a Chester Hill travel package?
Get set to save with an Expedia travel package. Bundle your airfares, rental cars and hotels and enjoy terrific discounts. Hotels aren't your only option, though. Book with us and take your pick of beachfront villas, chalets in the middle of mountains and even castles and houseboats!
Can I choose my airline with a Chester Hill Expedia holiday package?
With a holiday package, you're the one in charge. Whether you're looking to fly to Chester Hill in economy or first class, simply select from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Chester Hill holiday package?
It's difficult to predict what tomorrow might bring, so it's good to know that you can change or cancel your Chester Hill holiday package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it's an older booking, your airline, hotel or car rental company may charge a fee. Check our Customer Service Portal to find out more.

Popular places to visit

Circular Quay showing a city, central business district and modern architecture

Circular Quay

4.5/5(313 reviews)

Under the gaze of the magnificent Opera House and Harbour Bridge, Sydney’s transport hub is a terminal of unexpected beauty.

Circular Quay
Sydney Opera House

Sydney Opera House

4.5/5(293 reviews)

Take in a performance or just take in the splendour of one of the world’s most famous buildings.

Sydney Opera House
Sydney Harbour Bridge

Sydney Harbour Bridge

4.5/5(317 reviews)

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

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

S$52
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

S$34
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
Small Group Blue Mountains Tour with Dave's.

Blue Mountains Small Group Tour with Lunch, Zoo and Scenic World

S$245
per adult
Blue Mountains Small Group Tour with Lunch, Zoo and Scenic World
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.