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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Price found within the past 48 hours. Click for updated prices.
  • Rooftop terrace
    Aug 17 - Aug 28

    The Strand Hotel + Flight

    Darlinghurst
    9 nights
    3.0 star property
    8.6/10 - Excellent (200 reviews)
    "The hotel is quirky and the pub downstairs is very popular. I didn’t have any hot water to shower, except my first night, which made showering not possible."
    Reviewed June 5, 2026
    Roundtrip • Vancouver (YVR) - Sydney (SYD)
    YVR - SYD • 2 stops SYD - YVR • 2 stops
    CA $2,510
    CA $2,109
    per traveller
    found 1 day ago
    The Strand Hotel
  • Apartment | Outdoor dining
    Aug 1 - Aug 8

    Apartment With Pool Access, a Minute to the Beach + Flight

    Manly
    5 nights
    2.5 star property
    Roundtrip • Montreal (YUL) - Sydney (SYD)
    YUL - SYD • 2 stops SYD - YUL • 2 stops
    CA $5,684
    CA $3,264
    per traveller
    found 15 hours ago
    Apartment With Pool Access, a Minute to the Beach
  • Apartment | Reception
    Jul 29 - Aug 5

    Woolwich Studio Bliss, Private Oasis by the Water + Flight

    Woolwich
    5 nights
    2.5 star property
    8.0/10 - Very good (1 review)
    "Great location "
    Reviewed April 1, 2026
    Roundtrip • Montreal (YUL) - Sydney (SYD)
    YUL - SYD • 2 stops SYD - YUL • 2 stops
    CA $4,074
    CA $2,485
    per traveller
    found 10 hours ago
    Woolwich Studio Bliss, Private Oasis by the Water
  • Family Suite, 2 Bedrooms Bunk
    Aug 17 - Aug 28

    Rydges North Sydney + Flight

    North Sydney
    9 nights
    4.0 star property
    8.8/10 - Excellent (352 reviews)
    "Staff in every shift throughout my stay had been very resourceful and courteous . When I made an enquiry n/ or provided feedback , the duty person at the reception counter never failed to revert to me ."
    Reviewed June 7, 2026
    Roundtrip • Vancouver (YVR) - Sydney (SYD)
    YVR - SYD • 2 stops SYD - YVR • 2 stops
    CA $2,710
    CA $2,260
    per traveller
    found 1 day ago
    Rydges North Sydney
  • Signature Twin Room, Balcony, City View
    Sep 1 - Sep 7

    YEHS Hotel Sydney QVB + Flight

    Sydney Central Business District
    4 nights
    3.5 star property
    8.6/10 - Excellent (1,007 reviews)
    "Staff were lovely and the hotel was in a convenient spot. However, room was not up to our standards regarding cleanliness. Stains down the side of the bedside tables and the checkered layered on the top was peeling off. Rust in the bathroom. Small bugs on the ceiling. Wifi was awful- constantly lost connection in our room. Air conditioning didn’t work. Tv had a strange timer where it just randomly shut off. There is no ice machine or water available (outside of the sink) on site."
    Reviewed June 5, 2026
    Roundtrip • Edmonton (YEG) - Sydney (SYD)
    YEG - SYD • 1 stop SYD - YEG • 1 stop
    CA $2,913
    CA $2,465
    per traveller
    found 1 day ago
    YEHS Hotel Sydney QVB

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Three horses in the shade in a field on the Great Northern Road between Wiseman's Ferry and Bucketty, Yengo National Park, NSW, Australia

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 $174 per night from Jul 2 to Jul 3
CA $174
CA $192 total
Jul 2 - Jul 3
includes taxes & fees
9/10 Wonderful! (1,004 reviews)
"Very nice room and great breakfast. Only downside was no microwave in the room we stayed in."

Reviewed on Jun 8, 2026

Crowne Plaza Hawkesbury Valley by IHG
Windsor Riverview Inn

Windsor Riverview Inn

3 out of 5
47 George Street Windsor NSW
The price is CA $131 per night from Jun 23 to Jun 24
CA $131
CA $146 total
Jun 23 - Jun 24
includes taxes & fees
6.6/10 (327 reviews)
"Room was clean. Tv worked but could only access Network 10 channels only. Very disappointing."

Reviewed on May 3, 2026

Windsor Riverview Inn
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street Windsor NSW
The price is CA $108 per night from Jun 20 to Jun 21
CA $108
CA $120 total
Jun 20 - Jun 21
includes taxes & fees
5.2/10 (301 reviews)
"Permanent residents noisy"

Reviewed on May 31, 2026

Windsor Heritage Motel
See all 679 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 , 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

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

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

Circular Quay
Taronga Zoo

Taronga Zoo

This world-renowned zoo is cherished for its Sydney Harbour views and its residents.

Taronga Zoo

Things to do

Sydney: The Art of Indian Seven-Course Cooking Masterclass

Sydney: The Art of Indian Seven-Course Cooking Masterclass

CA $208
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
Hunter Valley Full Day Tour

Hunter Valley: Wine Tour with 2-Course Lunch, Choc & Cheese

CA $218
per adult
Hunter Valley: Wine Tour with 2-Course Lunch, Choc & Cheese
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.