Chester Hill Holidays from NZ$1,023

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

    • payments icon
    Better together
    Save up to NZ$616 when you book a flight and hotel together*
    lob hotels icon
    Find the right fit
    With over 300,000 hotels worldwide, it's easy to create a perfect package
    lob packages icon
    Rest easy
    Plan, book, and manage your trip all in one place

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
per person
18 Sept - 23 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.2/10 Very Good! (2,118 reviews)
Location is good close to public transport, unit was clean and tidy the only thing that let our stay down was outside street noise. Would happily recommend to others.

Reviewed on 25 Jun. 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
Save 100% on your flight
per person
21 Aug - 26 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
9.4/10 Exceptional! (1,003 reviews)
Very unique stay, wonderful management, and a great experience. I highly recommend

Reviewed on 24 Jun. 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
per person
18 Sept - 23 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.2/10 Very Good! (1,000 reviews)
A charming little hotel smack bang in the middle of Sydney. Short walk to town hall station and darling Harbour. We, husband and the wee one stayed in a 1 bedroom apartment room and had an excellent time

Reviewed on 23 Jun. 2025

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
per person
21 Aug - 26 Aug
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.6/10 Excellent! (1,002 reviews)
It was fine. Just fine. Also, there was a used razor in my shower, so can I assume my shower wasn’t cleaned between guests? Gross

Reviewed on 11 Jun. 2025

Rydges Sydney Central

Rydges Sydney Central

4.5 out of 5
Surry Hills
per person
18 Sept - 23 Sept
found 1 day ago
Return flight included
Auckland (AKL) to Sydney (SYD)
8.6/10 Excellent! (1,006 reviews)
Best Rydges by a mile. Great rooms helpful staff and fantastic spa pool pool gym. Could not be better - location is excellent too

Reviewed on 20 Jun. 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

3 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$297 per night from 27 July to 28 July
NZ$297
27 July - 28 July
includes taxes & fees
8.8/10 Excellent! (2,286 reviews)
"We loved the views and the staff were amazing..we'll definitely be coming back."

Reviewed on 26 Jun. 2025

Shangri-La Sydney
Hyatt Regency Sydney
Hyatt Regency Sydney
5 out of 5
161 Sussex Street, Sydney, NSW
Fully refundableReserve now, pay when you stay
The price is NZ$290 per night from 8 July to 9 July
NZ$290
8 July - 9 July
includes taxes & fees
8.8/10 Excellent! (1,729 reviews)
"Comfortable room with gorgeous view. Best breakfast selection we’ve had in ages! Will book again soon!"

Reviewed on 26 Jun. 2025

Hyatt Regency Sydney
The Fullerton Hotel Sydney
The Fullerton Hotel Sydney
5 out of 5
1 Martin Place, Sydney, NSW
Fully refundableReserve now, pay when you stay
The price is NZ$292 per night from 30 June to 1 July
NZ$292
30 June - 1 July
includes taxes & fees
9.2/10 Wonderful! (2,415 reviews)
"It’s convenient for transport options. But sound insulation of noise gets into the room which is disturbing to sleeping well. Bath room fixture is also rather poorly maintained eg doors can’t close well. Probably the lower end of Fullerton hotel I have ever experienced."

Reviewed on 26 Jun. 2025

The Fullerton Hotel Sydney
See all 5,427 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$1,023. 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

Sydney Opera House

Sydney Opera House

4.5/5(3,486 reviews)

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
Circular Quay showing street scenes, a city and a sunset

Circular Quay

4.5/5(4,882 reviews)

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 Harbour Bridge

Sydney Harbour Bridge

4.5/5(3,601 reviews)

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

Picture 11 for Activity Blue Mountains: Scenic World, Ferry, Zoo & Free Koala Photo

Blue Mountains: Scenic World, Ferry, Zoo & Koala Photo

NZ$215
per adult
92% of travellers recommend
Blue Mountains: Scenic World, Ferry, Zoo & Koala Photo
Sydney: Blue Mountains National Park Tour with River Cruise

Sydney: Blue Mountains National Park Tour with River Cruise

NZ$107
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
Sydney Hop-On Hop-Off Big Bus Tour

Big Bus Sydney Hop-On Hop-Off Sightseeing Tour

NZ$67
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing 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.