Windsor Holidays

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    Save up to S$134 when you book a flight and hotel together*

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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
Price was S$2,366, price is now S$1,844 per person
S$1,844
per person
6 Feb - 10 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Sydney (SYD)
8.2/10 Very Good! (2,388 reviews)
Good location but rooms need a renovation, we also ended up with an accessible bathroom and water from the shower went everywhere and there was no storage.

Reviewed on 5 Jan, 2026

3-bedroom Home in the Heart of Darlinghurst

3-bedroom Home in the Heart of Darlinghurst

2.5 out of 5
Darlinghurst
Price was S$3,097, price is now S$2,473 per person
S$2,473
per person
6 Feb - 10 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Sydney (SYD)
No reviews
Beachfront Manly Apartment With Balcony & Parking

Beachfront Manly Apartment With Balcony & Parking

2.5 out of 5
Manly
Price was S$2,832, price is now S$2,304 per person
S$2,304
per person
6 Feb - 10 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Sydney (SYD)
No reviews
Rydges Australia Square

Rydges Australia Square

4 out of 5
Sydney Central Business District
Price was S$2,253, price is now S$1,893 per person
S$1,893
per person
6 Feb - 10 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Sydney (SYD)
9.2/10 Wonderful! (1,714 reviews)
There was no breakfast served, but place is clean and comfortable except for the pilllows. Great location, close to Sydney Opera House, trains, etc.

Reviewed on 6 Jan, 2026

Ace Hotel Sydney

Ace Hotel Sydney

5 out of 5
Sydney Central Business District
Price was S$2,522, price is now S$2,162 per person
S$2,162
per person
6 Feb - 10 Feb
found 3 hours ago
Return direct flight included
Singapore (SIN) to Sydney (SYD)
9.4/10 Exceptional! (753 reviews)
The room design, the playful contemporary artwork, the friendly staff, the lobby bar, the records and the record player all cool without being pretentious, totally modern but welcoming and warm atmosphere

Reviewed on 3 Jan, 2026

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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Wisemans Ferry

You'll enjoy the cafes and riverfront in Wisemans Ferry. You might want to make time for a stop at Hawkesbury River or Wisemans Ferry Golf Club.

Find hotels in Wisemans Ferry

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$167 per night from 14 Jan to 15 Jan
S$167
14 Jan - 15 Jan
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Clean rooms. Friendly service. Excellent breakfast.

Reviewed on 2 Jan, 2026

Crowne Plaza Hawkesbury Valley by IHG
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street Windsor NSW
Fully refundableReserve now, pay when you stay
The price is S$125 per night from 9 Jan to 10 Jan
S$125
9 Jan - 10 Jan
includes taxes & fees
5.2/10 (293 reviews)
The motel is basic but suitable for my need.

Reviewed on 18 Sept, 2025

Windsor Heritage Motel
PARKROYAL Parramatta

PARKROYAL Parramatta

4.5 out of 5
30 Phillip Street Parramatta NSW
Fully refundableReserve now, pay when you stay
The price is S$163 per night from 11 Jan to 12 Jan
S$163
11 Jan - 12 Jan
includes taxes & fees
8.4/10 Very Good! (1,000 reviews)
Did not use the bar and paid for breakfast as part of my package

Reviewed on 27 Dec, 2025

PARKROYAL Parramatta
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$1,844, 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

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

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

Things to do

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

S$52
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

S$34
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
Small Group Blue Mountains Tour with Dave's.

Blue Mountains Small Group Tour with Lunch, Zoo and Scenic World

S$245
per adult
Blue Mountains Small Group Tour with Lunch, Zoo and Scenic World
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.