Windsor Vacation Packages

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Top Holiday Package Deals in Windsor

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
Save 100% on your flight
per person
Sep 22 - Sep 29
found 10 hours ago
Roundtrip flight included
Melbourne (AVV) 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 Jul. 14, 2025

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
per person
Sep 22 - Sep 29
found 10 hours ago
Roundtrip flight included
Melbourne (AVV) 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 Jun. 23, 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
Sep 22 - Sep 29
found 10 hours ago
Roundtrip flight included
Melbourne (AVV) 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 Jul. 9, 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
Sep 22 - Sep 29
found 10 hours ago
Roundtrip flight included
Melbourne (AVV) to Sydney (SYD)
9/10 Wonderful! (570 reviews)
wonderful get away, five star experience. Breakfast is a must!

Reviewed on Jun. 24, 2025

Ovolo Woolloomooloo

Ovolo Woolloomooloo

5 out of 5
Woolloomooloo
Save 100% on your flight
per person
Sep 22 - Sep 29
found 10 hours ago
Roundtrip flight included
Melbourne (AVV) to Sydney (SYD)
9.4/10 Exceptional! (1,004 reviews)
Nice stay noting overly wow

Reviewed on Jul. 10, 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(381 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
The price is CA $162 per night from Jul 21 to Jul 22
CA $162
CA $178 total
Jul 21 - Jul 22
includes taxes & fees
8.8/10 Excellent! (1,001 reviews)
"Everything we needed at our fingertips."

Reviewed on Jul. 3, 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 Jul. 11, 2025

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Tates Hotel Windsor
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street, Windsor, NSW
The price is CA $88 per night from Jul 22 to Jul 23
CA $88
CA $98 total
Jul 22 - Jul 23
includes taxes & fees
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 Jul. 1, 2025

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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Perhaps less than you might think --- from a tempting CA $677, 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

Sydney Opera House

Sydney Opera House

4.5/5(446 reviews)

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
Circular Quay featuring general coastal views, a sunset and central business district

Circular Quay

4.5/5(424 reviews)

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

Circular Quay
Sydney Harbour Bridge

Sydney Harbour Bridge

4.5/5(411 reviews)

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

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

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

CA $177
per adult
88% 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

CA $89
per adult
100% of travellers recommend
Sydney: Blue Mountains National Park Tour with River Cruise
Taronga Zoo Ticket with Hop-On Hop-Off Explorer Cruise

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

CA $76
per adult
88% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise
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.