Windsor Vacation Packages

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  • Better together

    Save up to CA $1,096 when you book a flight and hotel together*

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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
Price was CA $2,627, price is now CA $2,203 per person
CA $2,203
per person
May 24 - May 29
found 3 hours ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
8.6/10 Excellent! (1,004 reviews)
Close to shopping mall and all other attractions, room clean

Reviewed on Apr 13, 2026

The Old Clare by Ode Hotels

The Old Clare by Ode Hotels

4.5 out of 5
Chippendale
Price was CA $5,165, price is now CA $3,637 per person
CA $3,637
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
9.2/10 Wonderful! (563 reviews)
There was absolutely no staff Visibility to help with luggage we had to lug our own luggage to our rooms which is unheard of / previous owners had bell staff to take your luggage from the car - foyer areas are very run down - whole hotel needs a revamp as it’s looking very stayed - it is such a shame as we have been here many times under the old owners and loved it every time - this time we have been left wanting - even the rooftop bar was empty which tells you something - this used to ALwAyS be pumping …. Do better to stay competitive

Reviewed on Feb 28, 2026

YEHS Hotel Sydney CBD

YEHS Hotel Sydney CBD

3.5 out of 5
Sydney Central Business District
Price was CA $3,307, price is now CA $2,791 per person
CA $2,791
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sydney (SYD)
8.2/10 Very Good! (1,003 reviews)
Top location, couldn't beat the price. Was pleased that the family room had two separate rooms with a door. Helpful staff.

Reviewed on Apr 10, 2026

Rydges Australia Square

Rydges Australia Square

4 out of 5
Sydney Central Business District
Price was CA $2,610, price is now CA $2,256 per person
CA $2,256
per person
May 17 - May 22
found 1 day ago
Roundtrip flight included
Calgary (YYC) to Sydney (SYD)
9/10 Wonderful! (1,839 reviews)
Clean room, breakfast could have been hotter, didn't use parking facilities but hotel vlise yo everything.

Reviewed on Apr 14, 2026

Live in the Heart of Surry Hills - Walk to City

Live in the Heart of Surry Hills - Walk to City

2.5 out of 5
Surry Hills
Price was CA $3,259, price is now CA $2,826 per person
CA $2,826
per person
Jul 8 - Jul 12
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sydney (SYD)
8/10 Very Good! (2 reviews)

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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Berowra Waters

While visiting Berowra Waters, you might make a stop by sights like Berowra Waters Marina and Berowra Valley National Park.

Find hotels in Berowra Waters

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 $170 per night from Apr 27 to Apr 28
CA $170
CA $187 total
Apr 27 - Apr 28
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
Amazing staffs, beautiful location, clean room, lot of activities for kids, very enjoyable stay.

Reviewed on Apr 7, 2026

Crowne Plaza Hawkesbury Valley by IHG
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street Windsor NSW
The price is CA $114 per night from Apr 29 to Apr 30
CA $114
CA $125 total
Apr 29 - Apr 30
includes taxes & fees
5.2/10 (299 reviews)
Room sme

Reviewed on Mar 23, 2026

Windsor Heritage Motel
Windsor Riverview Inn

Windsor Riverview Inn

3 out of 5
47 George Street Windsor NSW
The price is CA $125 per night from Apr 16 to Apr 17
CA $125
CA $137 total
Apr 16 - Apr 17
includes taxes & fees
6.6/10 (324 reviews)
The room was very clean and comfortable. However, there was no toaster or crockery despite having a microwave, and the balcony door could barely be opened.

Reviewed on Nov 27, 2025

Windsor Riverview Inn
See all 625 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 $2,203, 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(453 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

Circular Quay

4.5/5(433 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(417 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

Sydney Hop-On Hop-Off Big Bus Tour

Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus

CA $60
per adult
86% of travellers recommend
Big Bus Sydney Hop-On Hop-Off Sightseeing Tour by Open-Top Bus
Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

CA $47
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
BridgeClimb Summit at Sydney Harbour Bridge

BridgeClimb Summit at Sydney Harbour Bridge

CA $300
per adult
98% of travellers recommend
BridgeClimb Summit at Sydney Harbour Bridge
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.