Chester Hill Holidays from AU$614

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Your Chester Hill Holiday

Make planning your travels simple by booking a holiday package to Chester Hill. We'll take care of the minutiae, so you can focus on savouring everything this neighbourhood has to offer. Not sure what to do and see during your trip to Chester Hill? Nearby attractions like Auburn Botanic Gardens, Crest Sporting Complex and Crest of Bankstown Reserve are good places to begin. Whatever your travel goals or budget, booking your perfect Chester Hill holiday is quick and easy with Expedia.

Top Holiday Package Deals in Chester Hill

Price found within the past 48 hours. Click for updated prices.
Stylish 2-bed House With Private Courtyard

Stylish 2-bed House With Private Courtyard

2.5 out of 5
Redfern
Price was AU$1,281, price is now AU$614 per person
AU$614
per person
13 June - 16 June
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
10/10 Exceptional! (1 review)
Excellent place for us to use as a base for vivisting Sydney for a short holiday. 5-10min walk from Redfern railway station meaning it was easy to move around the city.

Reviewed on 5 May 2026

Modern 3-bed With Pool & Water Views by Beach

Modern 3-bed With Pool & Water Views by Beach

2.5 out of 5
Cabarita
Price was AU$1,649, price is now AU$779 per person
AU$779
per person
18 June - 22 June
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
6/10 (1 review)
The whole suite is quite spacious with a spectacular view out the back. The living room is large but not a lot of seating, especially if your group/family is larger than 3-4. The neighborhood is very nice and maintained, we felt very safe. The cleanliness inside when we arrived was average. There’s a washing machine but not a dryer. We couldn’t use the pool because it was extremely filthy, the host said they would have it cleaned on the day we arrived but it didn’t get cleaned the entire time we were there (4 days) so we didn’t get to use it. Would I stay here again…Maybe

Reviewed on 27 Nov 2025

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
Price was AU$1,726, price is now AU$840 per person
AU$840
per person
26 June - 29 June
found 17 hours ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
No reviews
Spacious Stay Near Shops & Cafes in Marrickville

Spacious Stay Near Shops & Cafes in Marrickville

2.5 out of 5
Marrickville
Price was AU$1,526, price is now AU$743 per person
AU$743
per person
18 June - 22 June
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
No reviews
Bright 2-bed Apartment With Balcony & Garage

Bright 2-bed Apartment With Balcony & Garage

2.5 out of 5
Five Dock
Price was AU$1,394, price is now AU$684 per person
AU$684
per person
18 June - 22 June
found 1 day ago
Return flight included
Melbourne (MEL) 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

2 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

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 AU$325 per night from 11 May to 12 May
AU$325
11 May - 12 May
includes taxes & fees
9.2/10 Wonderful! (2,666 reviews)
Unbelievable views of Sydney harbor. Very comfortable room. The place to stay in Sydney by far.

Reviewed on 9 May 2026

Shangri-La Sydney
Four Seasons Hotel Sydney

Four Seasons Hotel Sydney

5 out of 5
199 George St. Sydney NSW
The price is AU$336 per night from 24 May to 25 May
AU$336
24 May - 25 May
includes taxes & fees
9.6/10 Exceptional! (2,186 reviews)
Fantastic location when visiting Sydney. The staff was amazing and very friendly Our room was very comfortable with a window seat that looked out towards the bridge. Highly recommend staying here!

Reviewed on 9 May 2026

Four Seasons Hotel 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 AU$269 per night from 24 May to 25 May
AU$269
24 May - 25 May
includes taxes & fees
8.8/10 Excellent! (2,032 reviews)
Only 3 of the 6 elevators appeared to be working (but there was no signage to confirm this) which resulted in my low mobility mother and I having to wait more than 25 minutes for an elevator to check out, at which point she had to force herself into an already full elevator while I took the stairs. ...

Reviewed on 8 May 2026

Hyatt Regency Sydney
See all 6,006 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.
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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 AU$614. 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

Circular Quay

Under the gaze of the magnificent Opera House and Harbour Bridge, Sydney’s transport hub is a terminal of unexpected beauty.

Circular Quay
Sydney Opera House

Sydney Opera House

Take in a performance or just take in the splendour of one of the world’s most famous buildings.

Sydney Opera House
Sydney Harbour Bridge

Sydney Harbour Bridge

An iconic structure on a beautiful harbour with breath-taking views at any time of day or night. Climb it, walk it, photograph it or just stand back and admire it.

Sydney Harbour Bridge

Activities

Sydney Harbour Cultural Cruise with Island Stop

Sydney Harbour Cultural Cruise with Island Stop

AU$83
per adult
Sydney Harbour Cultural Cruise with Island Stop
Sydney Harbour Discovery Cruise Including Lunch

Sydney Harbour Discovery Cruise Including Lunch

AU$79
per adult
96% of travellers recommend
Sydney Harbour Discovery Cruise Including Lunch
Sydney Opera House Official Guided Walking Tour

Sydney Opera House Official Guided Walking Tour

AU$50
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.