Windsor Holidays

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    Better together

    Save up to S$134 when you book a flight and hotel together*
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    Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package
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    Rest easy

    Plan, book, and manage your trip all in one place
Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
per person
1 Sept - 8 Sept
found 1 day ago
Return flight included
Singapore (SIN) 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 Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Save 100% on your flight
per person
1 Sept - 8 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.2/10 Very Good! (2,157 reviews)
The staff were excellent the apartment was roomy and the hotel has easy access to train , ferry and attractions

Reviewed on 14 Jul, 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
1 Sept - 8 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.6/10 Excellent! (1,007 reviews)
Nothing standout but a good, average hotel. I didn’t like that my room didn’t have a window to the outside, but I also get that it’s right in the heart of the CBD and that isn’t always possible. The staff were wonderful though, so kind, friendly, and helpful!

Reviewed on 9 Jul, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Save 100% on your flight
per person
1 Sept - 8 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
9/10 Wonderful! (570 reviews)
wonderful get away, five star experience. Breakfast is a must!

Reviewed on 24 Jun, 2025

Coogee Bay Boutique Hotel

Coogee Bay Boutique Hotel

4 out of 5
Coogee
Save 100% on your flight
per person
1 Sept - 8 Sept
found 1 day ago
Return flight included
Singapore (SIN) to Sydney (SYD)
8.8/10 Excellent! (820 reviews)
Great facility and location

Reviewed on 29 Jun, 2025

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
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Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(343 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

Top hotels in Windsor

Crowne Plaza Hawkesbury Valley by IHG
Crowne Plaza Hawkesbury Valley by IHG
4 out of 5
61 Hawkesbury Valley Way, Windsor, NSW
Fully refundable
The price is S$168 per night from 21 Jul to 22 Jul
S$168
21 Jul - 22 Jul
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Everything we needed at our fingertips."

Reviewed on 3 Jul, 2025

Crowne Plaza Hawkesbury Valley by IHG
Tates Hotel Windsor
Tates Hotel Windsor
3 out of 5
335 George St, Windsor, NSW
5.8/10 (70 reviews)
Comfortable to stay at
"Initially went past then found entrance off a side street. Quick book in. Parking availability limited.Nice bistro"

Reviewed on 11 Jul, 2025

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Tates Hotel Windsor
Windsor Heritage Motel
Windsor Heritage Motel
3 out of 5
54 George Street, Windsor, NSW
5.2/10 (283 reviews)
"Everything was diabolically dirty, theirs mould in bathroom, shower was brown, the basin sink tap was broken etc etc"

Reviewed on 1 Jul, 2025

Get rates
Windsor Heritage Motel
See all 619 properties in Windsor
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 Windsor holiday package cost?
Perhaps less than you might think --- from a tempting S$889, in fact! By combining flights, hotels and car rentals into a custom-built travel package, your Windsor escape is just clicks away.
How do I get a cheap travel package to Windsor?
If you love getting an amazing deal, combine your bookings into a Windsor holiday package. Whether you're looking for flights, hotels, rental cars or activities, you can book them all in one place. You'll have loads of choice at your fingertips too. Expedia has over 550 air carriers and 1,000,000 hotel options globally to choose from. Fly with who you want, check in where you like and save some cash --- now that's the perfect getaway!
Where should I stay in Windsor?
A trip to Windsor isn't complete without visiting Hawkesbury River, Hawkesbury Race Club and Lynwood Country Club. Spend your evenings close to these attractions and make sightseeing a breeze.
What are the top hotels in Windsor?
If it's your first visit to Windsor, lock in a room at Crowne Plaza Hawkesbury Valley, an IHG Hotel or Windsor Terrace Motel. Both will make you feel at home and are favourites with lots of travellers.
How far in advance should I book my Windsor holiday?
Reserving your flights early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to a year in advance. This is usually the cheapest time to book. If circumstances have left you booking late, low prices to Windsor will sometimes occur in the weeks leading up to departure.
What does an Expedia Windsor travel package include?
Expedia has all you need to book your Windsor escape, but what your package looks like depends on you. Choose from a combination of rental cars, flights and hotels. After some tours or experiences to fill in your time? Once you've made your booking, you can add them on too. No matter your budget or style, there's a package to suit your needs.
What should I know before booking a Windsor travel package?
A travel package can be customized for your circumstances and is a fantastic way to stretch your hard-earned dollars. What you include is completely up to you. Rental cars, hotels and flights --- come up with a combination that works with your plans.
Can I choose my airline with a Windsor Expedia holiday package?
Expedia has access to more than 550 airline partners globally, so you sure can! Just select your favourite carrier and put together your ideal Windsor trip.
If I'm not able to travel, can I cancel my Windsor holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Windsor holiday package. If you booked in the last 24 hours, you may be eligible for a refund. If your booking is older, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal for more information.

Popular places to visit

Sydney Opera House

Sydney Opera House

4.5/5(293 reviews)

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

Sydney Opera House
Circular Quay showing a city, central business district and modern architecture

Circular Quay

4.5/5(313 reviews)

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

Circular Quay
Sydney Harbour Bridge

Sydney Harbour Bridge

4.5/5(317 reviews)

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

Things to do

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

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

S$164
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

S$82
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
Blue Mountains Sunset & Three Sisters Small Group Tours

Blue Mountains Sunset & Three Sisters Tour Comfortable Wildlife Experience

S$121
per adult
96% of travellers recommend
Blue Mountains Sunset & Three Sisters Tour Comfortable Wildlife Experience
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. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.