Windsor Holidays

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Your Windsor Holiday

Book a holiday package to Windsor and immerse yourself in everything this fishing neighbourhood has to offer. With a reputation for watersports, cycling and culture, your next great adventure is waiting for you here. Eager to explore the sights during your trip to Windsor? Make sure you check out nearby attractions such as Hawkesbury River, Hawkesbury Race Club and Lynwood Country Club. No matter your travel plans or budget, booking your dream Windsor holiday is simple with Expedia.

Price found within the past 48 hours. Click for updated prices.
  • Apartment | Dining
    Jul 21 - Jul 28

    Chic 1-bed Retreat Near Shops & Beach + Flight

    Manly
    7 nights
    2.0 star property
    Return • Melbourne (AVV) - Sydney (SYD)
    AVV - SYD • Direct SYD - AVV • Direct
    AU$1,456
    AU$761
    per traveller
    found 1 day ago
    Chic 1-bed Retreat Near Shops & Beach
  • Front of property
    Aug 10 - Aug 19

    YEHS Hotel Sydney CBD + Flight

    Sydney Central Business District
    9 nights
    3.5 star property
    8.2/10 - Very good (1,000 reviews)
    "Centrally located. We love the location. Also the staff are helpful."
    Reviewed May 17, 2026
    Return • Adelaide (ADL) - Sydney (SYD)
    ADL - SYD • Direct SYD - ADL • Direct
    AU$2,502
    AU$1,094
    per traveller
    found 1 day ago
    YEHS Hotel Sydney CBD
  • Apartment | Living area
    Jul 21 - Jul 28

    Huge Harbour View Apartment In Historic Home + Flight

    Cremorne
    7 nights
    2.5 star property
    Return • Melbourne (AVV) - Sydney (SYD)
    AVV - SYD • Direct SYD - AVV • Direct
    AU$1,950
    AU$994
    per traveller
    found 1 day ago
    Huge Harbour View Apartment In Historic Home
  • Apartment | Living room
    Jul 30 - Aug 2

    3-bedroom Home in the Heart of Darlinghurst + Flight

    Darlinghurst
    3 nights
    2.5 star property
    10/10 - Exceptional (1 review)
    Return • Melbourne (AVV) - Sydney (SYD)
    AVV - SYD • Direct SYD - AVV • Direct
    AU$2,483
    AU$1,282
    per traveller
    found 5 hours ago
    3-bedroom Home in the Heart of Darlinghurst
  • Apartment | Marina
    Aug 16 - Aug 19

    Thriving City Location, Dining hub Near CBD + Flight

    Pyrmont
    3 nights
    2.5 star property
    Return • Melbourne (AVV) - Sydney (SYD)
    AVV - SYD • Direct SYD - AVV • Direct
    AU$1,513
    AU$799
    per traveller
    found 1 hour ago
    Thriving City Location, Dining hub Near CBD

Our guide on 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 Dharug National Park.

Find hotels in Wisemans Ferry

Our pick of the best 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 AU$171 per night from 11 June to 12 June
AU$171
11 June - 12 June
includes taxes & fees
9/10 Wonderful! (1,000 reviews)
"We love it here. Had a slight problem this time with one of the managers, but it got sorted. We will definitely stay again."

Reviewed on 15 May 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 AU$164 per night from 29 May to 30 May
AU$164
29 May - 30 May
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 3 May 2026

Windsor Riverview Inn
Windsor Heritage Motel

Windsor Heritage Motel

3 out of 5
54 George Street Windsor NSW
The price is AU$118 per night from 3 June to 4 June
AU$118
3 June - 4 June
includes taxes & fees
5.2/10 (300 reviews)
"Lots of cockroaches and glues onside of the room where we stayed. The towels are worn out. The floor looks terrible."

Reviewed on 24 Apr 2026

Windsor Heritage Motel
See all 671 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 Holidays
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beach holidays
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Frequently asked questions

How much does a Windsor holiday 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 holiday 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 favourites with lots of travellers.
How far in advance should I book my Windsor holiday?
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 holiday package?
Expedia has access to more than 550 airline partners globally, so you sure can! Just select your favourite carrier and put together your ideal Windsor trip.
If I'm not able to travel, can I cancel my Windsor holiday package?
It's impossible to predict what the future holds, so it's comforting to know that you can cancel or change your Windsor holiday 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(3,530 reviews)

Take in a performance or just take in the splendour of one of the world’s most famous buildings.

Sydney Opera House
Circular Quay

Circular Quay

4.5/5(4,930 reviews)

Under the gaze of the magnificent Opera House and Harbour Bridge, Sydney’s transport hub is a terminal of unexpected beauty.

Circular Quay
Sydney Harbour Bridge

Sydney Harbour Bridge

4.5/5(3,629 reviews)

An iconic structure on a beautiful harbour with breath-taking views at any time of day or night. Climb it, walk it, photograph it or just stand back and admire it.

Sydney Harbour Bridge

Activities

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

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

AU$86
per adult
88% of travellers recommend
Taronga Zoo Ticket with Hop-On Hop-Off Sydney Harbour Explorer Cruise
Sydney Harbour Cultural Cruise with Island Stop

Sydney Harbour Cultural Cruise with Island Stop

AU$83
per adult
Sydney Harbour Cultural Cruise with Island Stop
Sydney Harbour Discovery Cruise Including Lunch

Sydney Harbour Discovery Cruise Including Lunch

AU$79
per adult
96% of travellers recommend
Sydney Harbour Discovery Cruise Including Lunch
See all activities in Sydney

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.