Chester Hill Holidays
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Hotel Woolstore 1888, Sydney - Handwritten Collection
Pyrmont
€2,009
per person
28 Dec - 31 Dec
found 1 day ago
Return direct flight included
Dublin (DUB) to Sydney (SYD)
9.2/10 Wonderful! (1,000 reviews)
The location was great. It was a 15 minute walk to the Town Hall, and only a five minute walk to the train. The hotel was overall clean but we had a room with large stains on the area rug and the couch was old and dirty. The air conditioner would not work either. When we spoke to the staff at the front desk, there was no effort to have it checked out. It was miserably hot in the room.
Reviewed on 12 Oct 2026
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
3 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
Once the site of rusting railroad yards and wharves, one of Sydney’s greatest urban renewal projects now buzzes with museums, boutiques and eateries.
Sydney Olympic Park
1 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 Afterpay Arena or Accor Stadium while you're exploring the area.
Manly
This coastal suburb of Sydney is like something from a postcard, and a haven for surfers, swimmers and sunbakers.
Bondi Beach
1 out of top 10 points of interest in this area
Travellers to Bondi Beach praise its stunning beaches. If you've got some more time to explore, be sure to stop by Bondi Beach and Bondi Pavilion.
Top hotels in Chester Hill
Four Seasons Hotel Sydney
199 George St. Sydney NSW
Fully refundableReserve now, pay when you stay
€264
25 Oct - 26 Oct
includes taxes & fees
9.6/10 Exceptional! (2,273 reviews)
"Everything was amazing, staff, amenities, room, view. Lounge."
Reviewed on 16 Oct 2026
Hyatt Regency Sydney
161 Sussex Street Sydney NSW
Fully refundableReserve now, pay when you stay
€159
1 Nov - 2 Nov
includes taxes & fees
9/10 Wonderful! (2,193 reviews)
"Great central location"
Reviewed on 16 Oct 2026
Shangri-La Sydney
176 Cumberland Street The Rocks NSW
Fully refundableReserve now, pay when you stay
€199
25 Oct - 26 Oct
includes taxes & fees
9.2/10 Wonderful! (2,870 reviews)
"We had a great 14th wedding anniversary weekend with our eight-year-old daughter. The only criticism would be the double beds are a bit small for two adults but we could’ve got a bigger room just would’ve cost more level 36 is still as unreal as it always has been recommend to stay."
Reviewed on 16 Oct 2026
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 €1,925. 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.
Stay near popular Chester Hill attractions
Terry Lamb Complex
Explore the great outdoors at Terry Lamb Complex, a lovely green space in Sydney. Make some time to visit the shops while you're in the area.
Things to do
Blue Mountains Adventure: Scenic World, Zoo & Koala Photo
€132
per adult
94% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
€44
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.