Windsor Vacation Packages

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    Save up to CA $4,200 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.
Poolside Studio Retreat Near Oxford Street

Poolside Studio Retreat Near Oxford Street

2.5 out of 5
Darlinghurst
Price was CA $2,869, price is now CA $2,465 per person
CA $2,465
per person
Jan 25 - Jan 30
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
No reviews

Light-filled, Cosy Cbd-central Escape Terrace

Light-filled, Cosy Cbd-central Escape Terrace

2.5 out of 5
Surry Hills
Price was CA $3,057, price is now CA $2,529 per person
CA $2,529
per person
Jan 25 - Jan 30
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
No reviews

The Old Clare by Ode Hotels

The Old Clare by Ode Hotels

4.5 out of 5
Chippendale
Price was CA $6,312, price is now CA $5,458 per person
CA $5,458
per person
Dec 26 - Jan 2
found 6 hours ago
Roundtrip flight included
Vancouver (YVR) to Sydney (SYD)
9.2/10 Wonderful! (593 reviews)

InterContinental Sydney Double Bay by IHG

InterContinental Sydney Double Bay by IHG

5 out of 5
Double Bay
Price was CA $3,200, price is now CA $2,801 per person
CA $2,801
per person
Jan 25 - Jan 30
found 13 hours ago
Roundtrip flight included
Toronto (YTO) to Sydney (SYD)
9/10 Wonderful! (655 reviews)

Hotel Challis Potts Point

Hotel Challis Potts Point

3.5 out of 5
Potts Point
Price was CA $3,260, price is now CA $2,856 per person
CA $2,856
per person
Dec 9 - Dec 12
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Sydney (SYD)
8.6/10 Excellent! (918 reviews)

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
A tree in a grassy field with horses grazing nearby.

Wisemans Ferry

You'll enjoy the cafes and riverfront in Wisemans Ferry. You might want to make time for a stop at Hawkesbury River or Hawkins Lookout.

Find hotels in Wisemans Ferry

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 CA $176 per night from Nov 29 to Nov 30
CA $176
CA $193 total
Nov 29 - Nov 30
includes taxes & fees
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 $100 per night from Nov 9 to Nov 10
CA $100
CA $110 total
Nov 9 - Nov 10
includes taxes & fees
Windsor Heritage Motel
Visy Dior Hotel

Visy Dior Hotel

4 out of 5
1 Columbia Court Norwest NSW
Fully refundableReserve now, pay when you stay
The price is CA $121 per night from Dec 6 to Dec 7
CA $121
CA $134 total
Dec 6 - Dec 7
includes taxes & fees
8.4/10 Very good! (1,005 reviews)
"We had an excellent stay at this hotel and couldn't fault it. Everything was wonderful, and we thoroughly enjoyed our time there. We would definitely stay here again and would happily recommend it to other travellers."

Reviewed on Nov 2, 2026

Visy Dior Hotel
See all 695 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
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Beach Vacations
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Frequently asked questions

How much does a Windsor vacation package cost?
Perhaps less than you might think — from a tempting CA $2,465, 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.

Stay near popular Windsor attractions

Hawkesbury Regional Gallery

Enjoy an outing to Hawkesbury Regional Gallery during your stay in Sydney. Amble within the gardens or visit the spas in this relaxing area.
See properties

Things to do

Sydney: The Art of Indian Seven-Course Cooking Masterclass

Sydney: The Art of Indian Seven-Course Cooking Masterclass

CA $206
per adult
Sydney: The Art of Indian Seven-Course Cooking Masterclass
Sydney Attractions Pass including SEA LIFE Sydney Aquarium

Sydney Attractions Pass including SEA LIFE Sydney Aquarium

CA $51
per adult
86% of travellers recommend
Sydney Attractions Pass including SEA LIFE Sydney Aquarium
Sydney Opera House Official Guided Walking Tour

Sydney Opera House Official Guided Walking Tour

CA $49
per adult
96% of travellers recommend
Sydney Opera House Official Guided Walking 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.