Chester Hill Holidays

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

Haven Glebe

Glebe
S$1,361
per person
4 Dec - 9 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.8/10 Excellent! (1,000 reviews)
Great place to stay, helpful staff and amazing location

Reviewed on 8 Sept, 2026

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

Sydney Central Business District
Save 100% on your flight
S$1,458
per person
4 Dec - 9 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.4/10 Very good! (1,000 reviews)
Very central location…staff were nice. But a few warning signs on the floors advising guests to respect others and keep quiet would have been good. Was not impressed with noisy guests on my floor with little self awareness.

Reviewed on 11 Sept, 2026

Stylish Inner City 2-bed Unit by Fig Lane Park

Stylish Inner City 2-bed Unit by Fig Lane Park

Ultimo
Save 100% on your flight
S$1,634
per person
4 Dec - 9 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
No reviews
YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

Sydney Central Business District
S$1,492
per person
4 Dec - 9 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.6/10 Excellent! (1,004 reviews)
Bright Stay in Sydney With Harbour Bridge Views

Bright Stay in Sydney With Harbour Bridge Views

Surry Hills
S$1,461
per person
4 Dec - 9 Dec
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
No reviews

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
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

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.

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A nighttime cityscape with illuminated buildings reflecting on the water.

Darling Harbour

Once the site of disused railway yards and dilapidated wharves, one of Sydney’s greatest urban renewal projects has breathed life into this location once more.

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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

Unique features of Sydney Olympic Park include the theatres and live music. Make a stop by Accor Stadium or Sydney Olympic Park Athletic Centre while you're exploring the area.

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

Manly

This coastal suburb of Sydney is like something from a postcard, and a haven for surfers, swimmers and sunbakers.

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A beach with waves, a woman running, and buildings in the background.

Bondi Beach

1 out of top 10 points of interest in this area

Travellers to Bondi Beach praise its stunning beaches. If you've got some more time to explore, be sure to stop by Bondi Beach and Bondi Pavilion.

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Top hotels in Chester Hill

Shangri-La Sydney

Shangri-La Sydney

176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
S$327
21 Sept - 22 Sept
includes taxes & fees
9.2/10 Wonderful! (2,849 reviews)
"The room is clean and all staffs are courteous and professional. Room for improvement for housekeeping staff due to the following - did not refill soap bar, toilet paper, forks, plates inside the drawer of the round table in our room. Room should have been cleaned after the “do not disturb” sign ..."

Reviewed on 13 Sept, 2026

Shangri-La Sydney
Hyatt Regency Sydney

Hyatt Regency Sydney

161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
S$244
20 Sept - 21 Sept
includes taxes & fees
9/10 Wonderful! (2,167 reviews)
"Staff very kind & helpful"

Reviewed on 13 Sept, 2026

Hyatt Regency Sydney
Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
S$376
20 Sept - 21 Sept
includes taxes & fees
Four Seasons Hotel Sydney
See all 6,297 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$1,361. 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.

Stay near popular Chester Hill attractions

Terry Lamb Complex

Explore the great outdoors at Terry Lamb Complex, a lovely green space in Sydney. Make some time to visit the shops while you're in the area.
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Things to do

Sydney Hop-On Hop-Off Big Bus Tour

Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

S$58
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

S$47
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Opera House Official Guided Walking Tour

Sydney Opera House Official Guided Walking Tour

S$46
per adult
96% of travellers recommend
Sydney Opera House Official Guided Walking Tour
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.