Chester Hill Holidays from NZ$1,340

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Top Holiday Package Deals in Chester Hill

Price found within the past 48 hours. Click for updated prices.
Idyllic 4-bed Home With Alfresco Area Near Beach

Idyllic 4-bed Home With Alfresco Area Near Beach

2.5 out of 5
Dee Why
Save 100% on your flight
Price was NZ$2,238, price is now NZ$1,340 per person
NZ$1,340
per person
16 June - 19 June
found 16 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews
Central 2-bed Apartment With Private Parking

Central 2-bed Apartment With Private Parking

2 out of 5
Strathfield
Save 100% on your flight
Price was NZ$2,975, price is now NZ$1,669 per person
NZ$1,669
per person
27 July - 3 Aug
found 16 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
10/10 Exceptional! (1 review)
Gorgeous 3-bed Manly Pad, Short Walk to the Beach

Gorgeous 3-bed Manly Pad, Short Walk to the Beach

2 out of 5
Manly
Save 100% on your flight
Price was NZ$2,513, price is now NZ$1,461 per person
NZ$1,461
per person
16 June - 19 June
found 16 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews
Huge Harbour View Apartment In Historic Home

Huge Harbour View Apartment In Historic Home

2.5 out of 5
Cremorne
Save 100% on your flight
Price was NZ$2,577, price is now NZ$1,510 per person
NZ$1,510
per person
20 July - 25 July
found 14 hours ago
Return flight included
Wellington (WLG) to Sydney (SYD)
No reviews
Sunrise Cove 2-bed Apartment at Newport Beach

Sunrise Cove 2-bed Apartment at Newport Beach

2 out of 5
Newport
Save 100% on your flight
Price was NZ$2,356, price is now NZ$1,394 per person
NZ$1,394
per person
16 June - 19 June
found 16 hours ago
Return flight included
Auckland (AKL) to Sydney (SYD)
No reviews

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

Sydney Central Business District

3 out of top 10 points of interest in this area
4.5/5(8,638 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

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$410 per night from 1 June to 2 June
NZ$410
1 June - 2 June
includes taxes & fees
9.6/10 Exceptional! (2,178 reviews)
Instructions/explanations on services privided and room lightning.

Reviewed on 17 May 2026

Four Seasons Hotel Sydney
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$410 per night from 8 June to 9 June
NZ$410
8 June - 9 June
includes taxes & fees
9.2/10 Wonderful! (2,675 reviews)
Perfect. Excellent establishment, warm, courteous and very engaged staff. Wr stayed 8 days. Didn't want to leave!

Reviewed on 17 May 2026

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$329 per night from 1 June to 2 June
NZ$329
1 June - 2 June
includes taxes & fees
8.8/10 Excellent! (2,043 reviews)
Great location and in-house food was pretty good. Disappointed when the TV didn’t work for days. End of day be nice to have had that service. Didn’t get much help from the concierge. Other than that, was pretty good.

Reviewed on 17 May 2026

Hyatt Regency Sydney
See all 6,078 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$1,340. 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(3,530 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

Circular Quay

4.5/5(4,930 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(3,629 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

Sydney Hop-On Hop-Off Big Bus Tour

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

NZ$77
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
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

NZ$395
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
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.