Windsor Holidays from AU$665

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Your Windsor Holiday

Book a holiday package to Windsor and immerse yourself in everything this fishing neighbourhood has to offer. With a reputation for watersports, cycling and culture, your next great adventure is waiting for you here. Eager to explore the sights during your trip to Windsor? Make sure you check out nearby attractions such as Hawkesbury River, Hawkesbury Race Club and Lynwood Country Club. No matter your travel plans or budget, booking your dream Windsor holiday is simple with Expedia.

Top Holiday Package Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$1,047, price is now AU$665 per person
AU$665
per person
14 Nov - 16 Nov
found 1 day ago
Return flight included
Brisbane (BNE) to Sydney (SYD)
8.6/10 Excellent! (1,005 reviews)
Simply the best customer service!

Reviewed on 9 Oct 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$1,362, price is now AU$832 per person
AU$832
per person
27 Nov - 1 Dec
found 21 hours ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.2/10 Very Good! (1,002 reviews)
near townhall and QVB

Reviewed on 6 Oct 2025

YEHS Hotel Sydney Harbour Suites

YEHS Hotel Sydney Harbour Suites

4 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$1,428, price is now AU$886 per person
AU$886
per person
27 Nov - 1 Dec
found 21 hours ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
8.2/10 Very Good! (2,280 reviews)
Amenities and staff are lovely and really kind. They provided insightful recommendations on how to experience Sydney and also it waa very thoughtful of them to leave chocolates and wine in the room as I told them I was proposing that night to my girlfriend. Thanks Hanny, Susan, Buddhi and all others in the counter, you are the best.

Reviewed on 7 Oct 2025

APX Darling Harbour

APX Darling Harbour

3.5 out of 5
Sydney Central Business District
Save 100% on your flight
Price was AU$2,883, price is now AU$1,858 per person
AU$1,858
per person
29 Dec - 2 Jan
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
7.6/10 Good! (1,010 reviews)
Second time staying here and will stay again. Friendly staff, very convenient location at darling harbour. Comfortable rooms

Reviewed on 5 Oct 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
Price was AU$1,270, price is now AU$841 per person
AU$841
per person
2 Dec - 5 Dec
found 1 day ago
Return flight included
Adelaide (ADL) to Sydney (SYD)
9.2/10 Wonderful! (1,001 reviews)
Staff were very friendly and helpful! Easy to walk to most places. Great night sleep. Fun and quirky place. Book here and enjoy

Reviewed on 8 Oct 2025

Our guide on where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Default Image

Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(8,551 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 Windsor Hotel Deals

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 AU$199 per night from 14 Oct to 15 Oct
AU$199
14 Oct - 15 Oct
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"Clean and tidy, good staff and amenities."

Reviewed on 20 Sept 2025

Crowne Plaza Hawkesbury Valley by IHG
Windsor Riverview Inn

Windsor Riverview Inn

3 out of 5
47 George Street, Windsor, NSW
The price is AU$157 per night from 9 Nov to 10 Nov
AU$157
9 Nov - 10 Nov
includes taxes & fees
6.6/10 (321 reviews)
"Clean room"

Reviewed on 5 Oct 2025

Windsor Riverview Inn
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street, Windsor, NSW
The price is AU$140 per night from 11 Oct to 12 Oct
AU$140
11 Oct - 12 Oct
includes taxes & fees
5.2/10 (292 reviews)
"The motel is basic but suitable for my need."

Reviewed on 18 Sept 2025

Windsor Heritage Motel
See all 612 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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Frequently asked questions

How much does a Windsor holiday package cost?
Perhaps less than you might think — from a tempting AU$665, 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.

Discover the most popular places to visit in Windsor

Circular Quay showing street scenes, a city and a sunset

Circular Quay

4.5/5(4,882 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 Opera House

Sydney Opera House

4.5/5(3,486 reviews)

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

4.5/5(3,601 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

Activities

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

AU$62
per adult
84% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

AU$40
per adult
82% of travellers recommend
Sydney Tower Eye Tickets
Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise

Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise

AU$81
per adult
88% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise
See all activities in Sydney

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.