Chester Hill Holidays from NZ$1,581
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Top Holiday Package Deals in Chester Hill
Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney QVB
Sydney Central Business District
NZ$1,719
per person
20 Oct - 27 Oct
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.6/10 Excellent! (1,001 reviews)
Staff were helpful. Room was quiet and clean, though bathroom tiles were cracked in some places. Clean, but a bit worn. Room was small but efficient. Area of hotel is very convenient when getting train to/from airport. Short walking distance (15-20min) to Circular Quay, The Rocks and Opera House. Lots of supermarkets and restaurants in close proximity to get food as needed. Wonder if the room would get hot in summer as not too much control over room temp/fan.
Reviewed on 15 Aug 2026
Our guide on 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
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.
Darling Harbour
The best place to get acquainted with Sidney's nautical passions – sailing, pleasure-boating, whale watching – or the Maritime Museum if you prefer dry land.
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.
The Rocks
1 out of top 10 points of interest in this area
A noteworthy feature of The Rocks is its captivating waterfront views. While you're in town, be sure to stop and check out Circular Quay and Museum of Contemporary Art.
Manly
Venture to Sydney’s northern coast to explore this picturesque beach suburb, the perfect spot for surfing, shopping and sunbathing.
Our pick of the best Chester Hill Hotel Deals
Four Seasons Hotel Sydney
199 George St. Sydney NSW
NZ$409
23 Aug - 24 Aug
includes taxes & fees
9.6/10 Exceptional! (2,247 reviews)
"Very good"
Reviewed on 16 Aug 2026
Shangri-La Sydney
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
NZ$391
23 Aug - 24 Aug
includes taxes & 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 16 Aug 2026
Hyatt Regency Sydney
161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
NZ$323
13 Sept - 14 Sept
includes taxes & fees
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 NZ$1,581. 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.
Activities
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
NZ$62
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
NZ$77
per adult
86% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.