Windsor Holidays

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Price found within the past 48 hours. Click for updated prices.
Haven Glebe

Haven Glebe

4.5 out of 5
Glebe
Save 100% on your flight
Price was S$858, price is now S$499 per person
S$499
per person
5 Nov - 8 Nov
found 12 hours ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
8.8/10 Excellent! (960 reviews)
Hotel was clean and staff friendly and efficient. How ever it seems that this Hotel is the same as must Hotels in Australia, cooked Breakfast my be cooked but it is only like warm. Pityy as the food would be good

Reviewed on 24 Sept, 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Price was S$1,220, price is now S$535 per person
S$535
per person
5 Nov - 8 Nov
found 1 day ago
Return flight included
Melbourne (MEL) 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
Price was S$1,075, price is now S$561 per person
S$561
per person
5 Nov - 8 Nov
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
8.2/10 Very Good! (2,280 reviews)
The apartment was roomy, clean and very quiet. The bed was very comfy and location great.

Reviewed on 4 Oct, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was S$2,598, price is now S$1,608 per person
S$1,608
per person
5 Nov - 8 Nov
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
9/10 Wonderful! (584 reviews)
Quiet and convenient.

Reviewed on 23 Aug, 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
Price was S$1,164, price is now S$726 per person
S$726
per person
5 Nov - 8 Nov
found 1 day ago
Return flight included
Melbourne (MEL) to Sydney (SYD)
9.2/10 Wonderful! (1,001 reviews)
Great location. Quiet area, very walkable to the Royal Botanic Gardens, The Opera House. Staff was very friendly. Property was very cute.

Reviewed on 3 Oct, 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$169 per night from 8 Oct to 9 Oct
S$169
8 Oct - 9 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 S$129 per night from 21 Oct to 22 Oct
S$129
21 Oct - 22 Oct
includes taxes & fees
6.6/10 (319 reviews)
"the shower was hot and the bed was comfortable"

Reviewed on 14 Apr, 2025

Windsor Riverview Inn
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street, Windsor, NSW
The price is S$119 per night from 11 Oct to 12 Oct
S$119
11 Oct - 12 Oct
includes taxes & fees
5.2/10 (291 reviews)
"The motel is basic but suitable for my need."

Reviewed on 18 Sept, 2025

Windsor Heritage Motel
See all 605 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$499, 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

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 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
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

Small Group Blue Mountains Tour with Dave's.

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

S$243
per adult
Blue Mountains Small Group Tour with Lunch, Zoo and Scenic World
Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

S$52
per adult
84% 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
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.