Chester Hill Holidays from NZ$1,288

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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 Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Save 100% on your flight
Price was NZ$2,094, price is now NZ$1,288 per person
NZ$1,288
per person
21 Jan - 27 Jan
found 23 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
16.4/10 Exceptional! (2,388 reviews)
Room was a good size and clean. Bathroom could do with hand soap at basin

Reviewed on 13 Nov 2025

Airport Hotel Sydney

Airport Hotel Sydney

3.5 out of 5
Arncliffe
Save 100% on your flight
Price was NZ$4,223, price is now NZ$2,460 per person
NZ$2,460
per person
27 Dec - 3 Jan
found 9 hours ago
Return flight included
Christchurch (CHC) to Sydney (SYD)
12.4/10 Exceptional! (458 reviews)
Property was not as described, only thing good about it was it was close to the airport. Hard for taxis to pick up from.

Reviewed on 13 Nov 2025

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was NZ$3,238, price is now NZ$1,955 per person
NZ$1,955
per person
6 Feb - 13 Feb
found 14 hours ago
Return direct flight included
Hamilton (HLZ) to Sydney (SYD)
8.6/10 Excellent! (1,006 reviews)
Fantastic location and neat little hotel. Rooms on the small side, but good value for Sydney.

Reviewed on 17 Nov 2025

Stylish 3-bed Newport Stay With Balcony

Stylish 3-bed Newport Stay With Balcony

2.5 out of 5
Newport
Save 100% on your flight
Price was NZ$8,555, price is now NZ$5,199 per person
NZ$5,199
per person
27 Dec - 3 Jan
found 9 hours ago
Return flight included
Christchurch (CHC) to Sydney (SYD)
No reviews
InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Save 100% on your flight
Price was NZ$3,998, price is now NZ$2,511 per person
NZ$2,511
per person
21 Jan - 27 Jan
found 23 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
18/10 Exceptional! (596 reviews)
We will miss the hotel when it is gone

Reviewed on 2 Nov 2025

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
Default Image

Sydney Central Business District

1 out of top 10 points of interest in this area
4.5/5(8,551 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

Our pick of the best Chester Hill Hotel Deals

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 NZ$344 per night from 16 Dec to 17 Dec
NZ$344
16 Dec - 17 Dec
includes taxes & fees
9/10 Wonderful! (2,436 reviews)
Room was beautiful front desk staff lovely. The restaurant staff could use some training. But the rest was beautiful

Reviewed on 13 Nov 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 NZ$406 per night from 18 Dec to 19 Dec
NZ$406
18 Dec - 19 Dec
includes taxes & fees
9.6/10 Exceptional! (2,010 reviews)
Everything was 5 star as per usual. We love staying at the Four Seasons Hotel

Reviewed on 11 Nov 2025

Four Seasons Hotel Sydney
View Sydney

View Sydney

4 out of 5
17 Blue Street North Sydney NSW
Fully refundableReserve now, pay when you stay
The price is NZ$246 per night from 14 Dec to 15 Dec
NZ$246
14 Dec - 15 Dec
includes taxes & fees
9/10 Wonderful! (1,197 reviews)
The gentleman at check in was great.

Reviewed on 15 Nov 2025

View Sydney
See all 5,665 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 NZ$1,288. 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.

Discover the most popular places to visit in Chester Hill

Circular Quay showing street scenes, a city and a sunset

Circular Quay

Trains, buses and boats all make a bee-line for Circular Quay, a place at the heart of Sydney's journeying – and so should you.

Circular Quay
Sydney Opera House

Sydney Opera House

The bold lines of the Sydney Opera House speak more about Sydney than any other part of this cosmopolitan city of four million.

Sydney Opera House
Sydney Harbour Bridge

Sydney Harbour Bridge

A colossus of engineering, the Harbour Bridge brings the pieces of Sydney together, and offers you a different perspective on the city's wide-angle drama.

Sydney Harbour Bridge

Activities

Sydney Hop-On Hop-Off Big Bus Tour

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

NZ$71
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

NZ$62
per adult
84% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

NZ$34
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
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.