Windsor Vacations from ￥234,314

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to ￥45,448 when you book a flight and hotel together*

  • Find the right fit

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

  • Rest easy

    Plan, book, and manage your trip all in one place

The Latest Windsor Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Stamford Plaza Sydney Airport Hotel & Conference Centre

Stamford Plaza Sydney Airport Hotel & Conference Centre

4.5 out of 5
Mascot
Price was ￥280,245, price is now ￥234,314 per person
￥234,314
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Sydney (SYD)
8.6/10 Excellent! (1,257 reviews)
The room was spotless! Staff was nice .

Reviewed on Nov 10, 2025

Quest Bella Vista

Quest Bella Vista

4 out of 5
Bella Vista
Price was ￥334,833, price is now ￥254,788 per person
￥254,788
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Sydney (SYD)
9/10 Wonderful! (637 reviews)
Nice stay, clean and well maintained property.

Reviewed on Oct 13, 2025

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was ￥413,312, price is now ￥336,400 per person
￥336,400
per person
Dec 26 - Dec 30
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Sydney (SYD)
9/10 Wonderful! (587 reviews)
We will miss the hotel when it is gone

Reviewed on Nov 2, 2025

Rydges Darling Square Apartment Hotel

Rydges Darling Square Apartment Hotel

4 out of 5
Sydney Central Business District
Price was ￥286,123, price is now ￥235,351 per person
￥235,351
per person
Feb 2 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Sydney (SYD)
8.8/10 Excellent! (1,492 reviews)
Good friendly staff

Reviewed on Oct 29, 2025

YEHS Hotel Sydney QVB

YEHS Hotel Sydney QVB

3.5 out of 5
Sydney Central Business District
Price was ￥393,780, price is now ￥326,737 per person
￥326,737
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip non-stop flight included
Tokyo (HND) to Sydney (SYD)
8.6/10 Excellent! (1,006 reviews)
Location is ideal. Birthday present was a nice touch

Reviewed on Nov 10, 2025

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Sydney Town Hall featuring heritage architecture and a city

Sydney Central Business District

2 out of top 10 points of interest in this area
4.5/5(1,320 area reviews)

Historical and commercial heart of Sydney, the CBD boasts towering skyscrapers, lively café culture, and nightlife in areas like Darling Harbour. Explore parks such as Hyde Park and cultural institutions, while enjoying easy access to public transport.

Find hotels in Sydney Central Business District

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 ￥17,567 per night from Dec 11 to Dec 12
￥17,567
￥19,324 total
Dec 11 - Dec 12
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
Eggs tasteless

Reviewed on Nov 5, 2025

Crowne Plaza Hawkesbury Valley by IHG
Windsor Riverview Inn

Windsor Riverview Inn

3 out of 5
47 George Street, Windsor, NSW
6.6/10 (322 reviews)
Someone had scattered McDonald’s in the back yard and thrown some on the awning roof, It was there when I arrived and it was still there the next day when I left. Other than that, it was good. I would definitely stay there again.

Reviewed on Nov 2, 2025

Get rates
Windsor Riverview Inn
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street, Windsor, NSW
5.2/10 (293 reviews)
The motel is basic but suitable for my need.

Reviewed on Sep 18, 2025

Get rates
Windsor Heritage Motel
See all 602 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 vacation package cost?
Perhaps less than you might think — from a tempting ￥234,314, 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 vacation 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 favorites with lots of travelers.
How far in advance should I book my Windsor vacation?
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 vacation package?
Expedia has access to more than 550 airline partners globally, so you sure can! Just select your favorite carrier and put together your ideal Windsor trip.
If I'm not able to travel, can I cancel my Windsor vacation package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Windsor vacation 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 featuring general coastal views, modern architecture and a city

Circular Quay

Flanked by the Opera House and Harbour Bridge, Sydney’s transportation hub is one of the prettiest terminals in the world.

Circular Quay
Sydney Opera House showing a bay or harbor, modern architecture and a monument

Sydney Opera House

One of the world’s most famous buildings is surprisingly accessible; take in a show or just take a stroll to admire this astonishing building.

Sydney Opera House
Sydney Harbour Bridge showing night scenes, a bridge and a sunset

Sydney Harbour Bridge

Stroll from end-to-end or climb to the top; either way, Sydney’s “Coat Hanger” serves up memories to last a lifetime.

Sydney Harbour Bridge

Things to do

Sydney Tower Eye Tickets

Sydney Tower Eye Tickets

￥3,009
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

￥8,525
per adult
88% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise
Sydney Guided Sightseeing Bus Tour

Sydney Guided Sightseeing Bus Tour

￥4,914
per adult
86% of travellers recommend
Sydney Guided Sightseeing Bus Tour
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.